KR102390370B1 - Condensed cyclic compound and organic light emitting device including the same - Google Patents

Abstract

A condensed cyclic compound and an organic light emitting device including the condensed cyclic compound are provided.

Description

Condensed cyclic compound and organic light emitting device including the same

A condensed cyclic compound and an organic light emitting device including the same are 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, driving voltage and response speed characteristics, and can be multicolored.

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. Carriers such as 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.

It is to provide a novel condensed cyclic compound and an organic light emitting device employing the same.

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

<Formula 1>

in Formula 1 above

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₁₂ )(R ₁₃ ), Si(R ₁₂ )(R ₁₃ ), P(R ₁₂ ) or P(=O)(R ₁₂ ), f1 and f2 are, independently of each other, 0 or 1, and f1 + f2 is 1;

X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₂₂ )(R ₂₃ ), Si(R ₂₂ )(R ₂₃ ), P(R ₂₂ ) or P(=O)(R ₂₂ ), f3 and f4 are, independently of each other, 0 or 1, and f3+f4 is 1;

X ₃₁ to X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ];

g1 and g2 are, independently of each other, 0, 1 or 2, and g1 + g2 is 2;

i) In Formula 1, when f1=1, f2=0, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N -[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] is not, ii) f1=1, f2=0, f3=1, f4=0, g1=1 and g2=1 in Formula 1, and X ₁₁ when is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], then X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ), iii) In Formula 1, when f1=1, f2=0, f3=0, f4=1, g1=0, and g2=2, and X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N -[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], iv) in Formula 1, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ When C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ), v) in Formula 1 above If f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], then X ₂₁ is C (R ₂₂ ) not (R ₂₃ ), vi) in Formula 1, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], vii) in Formula 1 above, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1; , when X ₁₁ is Si(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], viii) f1=0, f2=1 in Formula 1 , f3=0, f4=1, g1=1 and g2=1, and X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _{b 11} ], then X ₂₁ is not C(R ₂₂ )(R ₂₃ );

L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ hetero Arylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group (substituted or unsubstituted divalent non -aromatic condensed heteropolycyclic group);

a1 to a3, a11 and a12 are each independently selected from an integer of 0 to 5;

R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alke nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensation polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ ) (Q ₇ );

b1 to b3, b11 and b21 are each independently selected from an integer of 1 to 5;

c1 is an integer selected from 1 to 4;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,

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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one; 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ 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 or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non- It is selected from the aromatic heterocondensed polycyclic group.

According to another aspect, the first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode, including a light emitting layer, and including at least one type of condensed cyclic compound represented by Formula 1;

The condensed cyclic compound may be included in the light emitting layer, the light emitting layer may further include a dopant, and the condensed cyclic compound included in the light emitting layer may serve as a host.

Since the condensed cyclic compound has excellent electrical properties and thermal stability, an organic light emitting device employing the condensed cyclic compound may have low driving voltage, high efficiency, high luminance, and long lifespan.

1 is a cross-sectional view schematically illustrating an organic light emitting diode according to an exemplary embodiment.

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

<Formula 1>

in Formula 1 above

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₁₂ )(R ₁₃ ), Si(R ₁₂ )(R ₁₃ ), P(R ₁₂ ) or P(=O)(R ₁₂ ), f1 and f2 are, independently of each other, 0 or 1, and f1 + f2 is 1;

X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₂₂ )(R ₂₃ ), Si(R ₂₂ )(R ₂₃ ), P(R ₂₂ ) or P(=O)(R ₂₂ ), f3 and f4 are, independently of each other, 0 or 1, and f3+f4 is 1;

X ₃₁ to X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ];

g1 and g2 are, independently of each other, 0, 1 or 2, and g1 + g2 is 2;

i) In Formula 1, when f1=1, f2=0, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N -[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] is not, ii) f1=1, f2=0, f3=1, f4=0, g1=1 and g2=1 in Formula 1, and X ₁₁ when is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], then X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ), iii) In Formula 1, when f1=1, f2=0, f3=0, f4=1, g1=0, and g2=2, and X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N -[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], iv) in Formula 1, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ When C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ), v) in Formula 1 above If f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], then X ₂₁ is C (R ₂₂ ) not (R ₂₃ ), vi) in Formula 1, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1, and when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], vii) in Formula 1 above, f1=0, f2=1, f3=1, f4=0, g1=1 and g2=1; , when X ₁₁ is Si(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], viii) f1=0, f2=1 in Formula 1 , f3=0, f4=1, g1=1 and g2=1, and X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _{b 11} ], then X ₂₁ is not C(R ₂₂ )(R ₂₃ );

L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ hetero Arylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group (substituted or unsubstituted divalent non -aromatic condensed heteropolycyclic group);

a1 to a3, a11 and a12 are each independently selected from an integer of 0 to 5;

R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alke nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensation polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ ) (Q ₇ );

b1 to b3, b11 and b21 are each independently selected from an integer of 1 to 5;

c1 is an integer selected from 1 to 4;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,

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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one; 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ 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 or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non- It is selected from the aromatic heterocondensed polycyclic group.

For a description of each substituent in Formula 1, refer to the description in the present specification.

The condensed cyclic compound may be represented by one of Formulas 1-1 to 1-12:

<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 1-7>

<Formula 1-8>

<Formula 1-9>

<Formula 1-10>

<Formula 1-11>

<Formula 1-12>

In Formulas 1 and 1-1 to 1-12, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, S(=O), S(=O) ₂ , C (=O), C(R ₁₂ )(R ₁₃ ), Si(R ₁₂ )(R ₁₃ ), P(R ₁₂ ), or P(=O)(R ₁₂ ); X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₂₂ )(R ₂₃ ), Si(R ₂₂ )(R ₂₃ ), P(R ₂₂ ) or P(=O)(R ₂₂ ).

According to one embodiment, in Formulas 1 and 1-1 to 1-12, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, C(R ₁₂ )(R ₁₃ ) ) or Si(R ₁₂ )(R ₁₃ ); X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, C(R ₂₂ )(R ₂₃ ) or Si(R ₂₂ )(R ₂₃ ), but is not limited thereto.

In Formulas 1 and 1-1 to 1-12, X ₃₁ to X ₃₄ may each independently represent N or C-[(L ₂ ) _a2 -(R ₂ ) _b2 ].

When two or more of X ₃₁ to X ₃₄ in Formulas 1 and 1-1 to 1-12 are C-[(L ₂ ) _a2 -(R ₂ ) _b2 ], they may be different from or the same as each other.

According to one embodiment, all of X ₃₁ to X ₃₄ in Formulas 1 and 1-1 to 1-12 may be C-[(L ₂ ) _a2 -(R ₂ ) _b2 ].

Accordingly, the condensed cyclic compound may be represented by one of the following Chemical Formulas 1A-1 to 1A-12:

<Formula 1A-1>

<Formula 1A-2>

<Formula 1A-3>

<Formula 1A-4>

<Formula 1A-5>

<Formula 1A-6>

<Formula 1A-7>

<Formula 1A-8>

<Formula 1A-9>

<Formula 1A-10>

<Formula 1A-11>

<Formula 1A-12>

In Formulas 1A-1 to 1A-12, X ₁₁ , X ₂₁ , L ₁ to L ₃ , a1 to a3 , R ₁ to R ₇ and c1 are described in the present specification, and c2 is 1 to 4 is selected from among the integers of

The condensed cyclic compound is

i) In Formula 1-2, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

ii) In Formula 1-2, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C( R ₂₂ ) (R ₂₃ ) not,

iii) In Formula 1-4, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

iv) In Formula 1-8, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ) ), not

v) In Formula 1-8, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is not C(R ₂₂ )(R ₂₃ ),

vi) In Formula 1-8, when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

vii) in Formula 1-8, when X ₁₁ is Si(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

viii) In Formula 1-11, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is not C(R ₂₂ )(R ₂₃ ).

Accordingly, when the condensed cyclic compound is represented by Formula 1-2, it is represented by one of Formulas 1A-2-1 to 1A-2-22, and when the condensed cyclic compound is represented by Formula 1-4, It is represented by one of Formulas 1A-4-1 to 1A-4-24, and when the condensed cyclic compound is represented by Formula 1-8, it is represented by one of Formulas 1A-8-1 to 1A-8-20 , When the condensed cyclic compound is represented by Formula 1A-11, it may be represented by one of Formulas 1A-11-1 to 1A-11-24, but is not limited thereto:

For example, Formula 1A-2-10 has a backbone of Formula 1A-2, wherein X ₁₁ is O, X ₁₂ is O, and Formula 1A-2-14 is represented by Formula 1A-2 has a backbone, wherein X ₁₁ is S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ]:

<Formula 1A-2-10>

<Formula 1A-2-14>

Formulas 1A-2-1 to 1A-2-22, 1A-4-1 to 1A-4-24, 1A-8-1 to 1A-8-20, and 1A-11-1 to 1A-11-24 The structure can be understood with reference to the above.

According to one embodiment, the condensed cyclic compound,

represented by one of Formulas 1-1 to 1-7 and 1-9 to 1-12,

In Formulas 1-1 to 1-7 and 1-9 to 1-12,

X ₁₁ and X ₁₂ are each independently O or S;

X ₁₁ is O or S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] or C(R ₂₂ )(R ₂₃ );

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] or C(R ₁₂ )(R ₁₃ ), and X ₁₂ is O or S; or

X ₁₁ may be C(R ₁₂ )(R ₁₃ ), and X ₁₂ may be C(R ₂₂ )(R ₂₃ ).

According to another embodiment, the condensed cyclic compound,

represented by one of Formulas 1A-1 to 1A-7 and 1A-9 to 1A-12,

In Formulas 1A-1 to 1A-7 and 1A-9 to 1A-12,

X ₁₁ and X ₁₂ are each independently O or S;

X ₁₁ is O or S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] or C(R ₂₂ )(R ₂₃ );

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] or C(R ₁₂ )(R ₁₃ ), and X ₁₂ is O or S; or

X ₁₁ may be C(R ₁₂ )(R ₁₃ ), and X ₁₂ may be C(R ₂₂ )(R ₂₃ ).

According to another embodiment, the condensed cyclic compound is represented by one of Chemical Formulas 1-1, 1-3 to 1-7, and 1-9 to 1-11, and Chemical Formulas 1-1, 1-3 to 1 In -7 and 1-9 to 1-11, X ₁₁ may be N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ may be N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ]. there is.

According to another embodiment, the condensed cyclic compound is represented by one of Formulas 1A-1, 1A-3 to 1A-7, and 1A-9 to 1A-11, and Formulas 1A-1, 1A-3 to 1A In -7 and 1A-9 to 1A-11, X ₁₁ may be N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ may be N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] there is.

According to another embodiment, the condensed cyclic compound is represented by Formula 1-2, in Formula 1-2, X ₁₁ is O or S, and X ₁₂ is O, S or N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to another embodiment, the condensed cyclic compound is represented by Formula 1A-2, wherein in Formula 1A-2, X ₁₁ is O or S, and X ₁₂ is O, S or N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to one embodiment, the condensed cyclic compound is represented by one of Formulas 1-1 to 1-7 and 1-9 to 1-12, wherein Formulas 1-1 to 1-7 and 1-9 to 1- X ₁₁ of 12 may be O or S. The condensed cyclic compound in which X ₁₁ is O or S may have improved planarity and excellent charge mobility due to one pair of electrons of O and S.

In Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12 and Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently, substituted or unsubstituted C ₃ - C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl Rene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic) condensed polycyclic group), and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group).

According to one embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently,

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, ace Naphthylene group (acenaphthylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrenylene), anthracenylene group (anthracenylene), fluoranxenylene group ( fluoranthenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene (pentaphenylene), hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinyl Ren group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene), isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, Cinnolinylene, carbazolylene, phenanthridinylene , acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofura Nylene group (benzofuranylene), thiophenylene group (thiophenylene), benzothiophenylene group (benzothiophenylene), thiazolylene group (thiazolylene), isothiazolylene group (isothiazolylene), benzothiazolylene group (benzothiazolylene), isoxazolylene group (isoxazolylene) ), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and

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 ₂₀ aryl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, substituted with at least one of a condensed heterocyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cri Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; can be selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , it may be selected from a cinolinyl group and a quinazolinyl group.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12 and Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are

a phenylene group, a naphthylene group, and a triphenylene group; and

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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, and a chrysenyl group substituted with at least one, a phenylene group, a naphthylene group, and a triphenylene group; may be selected from, but is not limited thereto.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently selected from Formula 1 It may be one of 2-1 to 2-34:

In Formulas 2-1 to 2-34,

Y ₁ is O, S, S(=O), S(=O) ₂ , C(Z ₃ )(Z ₄ ), N(Z ₅ ), or Si(Z ₆ )(Z ₇ );

Z ₁ To Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenane Threnyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinoli a nyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carba Zolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxali selected from a nyl group, a cinolinyl group, and a quinazolinyl group;

d1 is an integer from 1 to 4, d2 is an integer from 1 to 3, d3 is an integer from 1 to 6, d4 is an integer from 1 to 8, d5 is 1 or 2, and d6 is an integer from 1 to 5 ego;

* and *' are binding sites with neighboring atoms, respectively.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently selected from Formula 1 It may be selected from the group represented by 3-1 to 3-21, but is not limited thereto:

* and *' are binding sites with neighboring atoms, respectively.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group;

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, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, and triazinyl group substituted with at least one of, phenylene group, naphthylene group, pyridinyl a ren group, a pyrimidinylene group, and a triazinylene group; may be selected from, but is not limited thereto.

In Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, a1 represents the number of L ₁ , and is 0, 1, 2, 3, 4 or 5, for example For example, it may be 0, 1 or 2, as another example 0 or 1. When a1 is 0, *-(L ₁ ) _a1 -*' becomes a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2, a3, a11, and a12 may be understood with reference to the description of a1, Chemical Formulas 1, 1-1 to 1-12, 1A-1 to 1A-12, and Chemical Formulas in Table 1.

In Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12 and Table 1, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently selected from hydrogen; 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 A salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , 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 ), and -B(Q ₆ )(Q ₇ ).

According to one embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid Or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted A substituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q ₃ )(Q ₄ ) ) (Q ₅ ) may be selected.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas 1 to 1, i) X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) ) at least one of R ₃ and R ₁₁ when _b11 ], ii) at least one of R ₃ and R ₂₁ when X ₁₂ is N-[(L ₂₁ ) _a11 -(R ₂₁ ) _b11 ], and iii) X When ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₂₁ ) _a11 -(R ₂₁ ) _b11 ], then at least one of R ₃ , R ₁₁ and R ₂₁ . are, independently of each other, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or It may be selected from an unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas 1 to 1, R ₃ is a substituted, including at least one nitrogen atom as a ring constituent atom. or an unsubstituted C ₁ -C ₃₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, but is not limited thereto.

According to another embodiment, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in Formulas 1, 1-1 to 1-12 and 1A-1 to 1A-12 and Table 1 are independent of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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 and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Cenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), a triazinyl group, a dibenzofuranyl group (dibenzofuranyl), a dibenzothiophenyl group (dibenzothiophenyl), a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si( _Q33 )( _Q34 )( _Q35 ) At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, Hexasenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group , indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, Phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra a zolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It may be selected from an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in Formulas 1, 1-1 to 1-12 and 1A-1 to 1A-12 and Table 1 are independently of each other, 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a group represented by the following formulas 4-1 to 4-31, and -Si(Q ₃ )(Q ₄ )( Q ₅ );

Wherein Q ₃ To Q ₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto:

In Formulas 4-1 to 4-31,

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

Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group An 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, a pyrenyl group, a phenanthrenyl group, a fluorine group Nyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group selected from a nyl group, a quinazolinyl group, a quinoxalinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina selected from a jolinyl group and a quinoxalinyl group;

e1 is an integer from 1 to 5, e2 is an integer from 1 to 7, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is 1 or 2, and e6 is an integer from 1 to 6 , and * is a binding site with a neighboring atom.

According to another embodiment, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in Formulas 1, 1-1 to 1-12 and 1A-1 to 1A-12 and Table 1 are independently of each other, 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a group represented by the following formulas 5-1 to 5-55, and -Si(Q ₃ )(Q ₄ ) (Q ₅ );

Wherein Q ₃ To Q ₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto:

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, R ₁ , R ₂ and R ₄ to R ₇ may be hydrogen, The present invention is not limited thereto.

In Formulas 1, 1-1 to 1-12, 1A-1 to 1A-12, and Formulas in Table 1, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 5. For example, b1 may be 1 or 2. As another example, b1 may be 1. When b1 is two or more, two or more R ₁ may be the same as or different from each other. Descriptions of b2 to b3, b11, and b12 may be understood with reference to the description of b1, Chemical Formulas 1, 1-1 to 1-12, 1A-1 to 1A-12, and Chemical Formulas in Table 1.

In Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Formulas in Table 1, c1 represents the number of -[(L ₁ ) _a1 -(R ₁ ) _b1 ], and 1 to 4 may be selected from integers of . For example, c1 is 1 or 2. When c1 is 2 or more, two or more -[(L ₁ ) _a1 -(R ₁ ) _b1 ] may be the same as or different from each other.

When X ₁₁ in Formulas 1, 1-1 to 1-12, 1A-1 to 1A-12 and Table 1 is C(R ₁₂ )(R ₁₃ ) or Si(R ₁₂ )(R ₁₃ ) , R ₁₂ and R ₁₃ may be the same as or different from each other. For example, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), various modifications are possible, such as R ₁₂ may be a methyl group and R ₁₃ may be a phenyl group.

When X ₂₁ in Formulas 1, 1-1 to 1-12 and 1A-1 to 1A-12 and Table 1 is C(R ₂₂ )(R ₂₃ ) or Si(R ₂₂ )(R ₂₃ ) , R ₂₂ and R ₂₃ may be the same as or different from each other. For example, when X ₂₁ is C(R ₂₂ )(R ₂₃ ), various modifications are possible, for example, R ₂₂ may be a methyl group and R ₂₃ may be a phenyl group.

In Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12 and Table 1, L ₃ is a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent ratio -Selected from a condensed aromatic polycyclic group, and R ₃ may be selected from a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group.

For example, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Formulas in Table 1, L ₃ is,

a phenylene group, a naphthylene group, and a triphenylene group; and

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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, and a chrysenyl group substituted with at least one, a phenylene group, a naphthylene group, and a triphenylene group; is selected from

R ₃ may be selected from Formulas 4-1 to 4-5.

According to another embodiment, L ₃ is selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and R ₃ is substituted or unsubstituted C ₆ The condensed cyclic compound represented by Formula 1 selected from a -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group may be included, for example, in a hole transport region of an organic light emitting device to be described later.

According to another embodiment, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas 1 to 1, R ₃ may be an electron transporting moiety. For example, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted It may be a cyclic monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in Formulas in Table 1, R ₃ may be selected from the group represented by Formulas 4-6 to 4-25. However, the present invention is not limited thereto.

According to another embodiment, the condensed cyclic compound represented by Formula 1, wherein R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, For example, it may be included in a light emitting layer of an organic light emitting device to be described later.

The condensed cyclic compound may be one of the following compounds 1 to 167, but is not limited thereto:

The condensed cyclic compound represented by Formula 1 has a core having a strong structure in which a plurality of rings are fused to each other as shown in Formula 1, and a relatively high T _g (eg, 130° C. or higher T _g ) and a relatively low T _ev (eg, T _ev of 350° C. or less). Accordingly, the condensed cyclic compound represented by Formula 1 may have excellent process heat resistance.

In addition, in the condensed cyclic compound represented by Formula 1, various groups may exist in X ₁₁ and X ₂₁ in Formula 1 (for the list of X ₁₁ and X ₂₁ in Formula 1, refer to the bar described herein), a molecule It may have a bipolar structure in which the heavy electron transport moiety and the hole transport moiety are evenly distributed. Thereby, it is possible to have HOMO, LUMO and T ₁ energy levels suitable for use as a material for an electrical device, for example an organic light emitting device (eg, a host or hole transport layer material for an organic light emitting device).

For example, simulation evaluation results using Gaussian for HOMO, LUMO and T ₁ energy levels for compounds 50, 59 to 63, 153, 154, 158 to 166 are shown in Table 2:

compound No. HOMO (eV) LUMO (eV) T ₁ (eV) 50 -5.101 -1.734 2.783 59 -5.007 -1.784 2.675 60 -5.013 -1.807 2.683 61 -5.137 -1.757 2.778 62 -5.074 -1.804 2.658 63 -4.971 -1.777 2.565 153 -5.302 1.845 2.793 154 -5.041 -1.743 2.759 158 -5.089 -1.812 2.708 159 -5.005 -1.738 2.677 160 -5.042 -1.809 2.657 161 -5.374 -1.799 2.781 162 -5.236 -1.846 2.680 163 -5.047 -1.729 2.712 164 -5.323 -1.805 2.696 165 -5.329 -1.862 2.619 166 -5.407 -1.767 2.734

From Table 2, the condensed cyclic compound represented by Formula 1 is a material for an electric device, for example, a material for an organic light emitting device (for example, HOMO suitable for use as a host or hole transport layer material of an organic light emitting device); It can be seen that LUMO and T ₁ have energy levels.

According to one embodiment, the condensed cyclic compound represented by Formula 1 may be used as a green phosphorescent host or a hole transport layer material for an organic light emitting device, but is not limited thereto.

A method for synthesizing the condensed cyclic compound represented by Formula 1 can be easily recognized by those skilled in the art with reference to the Synthesis Examples to be described later.

The condensed cyclic compound represented by Formula 1 may be suitable for use as a host of an organic layer of an organic light emitting device, for example, a light emitting layer of the organic layer. a second electrode; and an organic layer interposed between the first electrode and the second electrode, including a light emitting layer, and including at least one type of condensed cyclic compound represented by Formula 1;

The organic light emitting device may have a low driving voltage, high efficiency, high luminance, and long lifespan by having the organic layer including the condensed cyclic compound represented by Formula 1 as described above.

The condensed cyclic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting diode. For example, the condensed cyclic compound may include a light emitting layer, a hole transport region between the first electrode and the light emitting layer (eg, including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer), and between the light emitting layer and the second electrode may be included in at least one of the electron transport region (eg, including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer). For example, the condensed cyclic compound represented by Formula 1 may be included in at least one of the emission layer and the hole transport region. In this case, when the condensed cyclic compound is present in the light emitting layer, the light emitting layer may further include a dopant, and the condensed cyclic compound included in the light emitting layer may serve as a host. The emission layer may be a green emission layer emitting green light, and the dopant may be a phosphorescent dopant.

In the present specification, "(organic layer) includes one or more condensed cyclic compounds" means "(organic layer) 1 type of condensed cyclic compound belonging to the scope of Formula 1 or two different types of fused cyclic compound belonging to the scope of Formula 1 above" may include more than one condensed cyclic compound".

For example, the organic layer may include only Compound 1 as the condensed cyclic compound. In this case, the compound 1 may be present in the emission layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the condensed cyclic compound. In this case, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light emitting layer) or exist in different layers (eg, the compound 1 is the light emitting layer) , and the compound 2 may be present in the hole transport layer).

For example, the first electrode is an anode, the second electrode is a cathode, and the organic layer is i) interposed between the first electrode and the light emitting layer, and is at least one of a hole injection layer, a hole transport layer, and an electron blocking layer. a hole transport region comprising one; and ii) an electron transport region interposed between the emission layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

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

According to another embodiment, the organic layer of the organic light emitting device includes at least one of a first compound represented by the following Chemical Formula 41 and a second compound represented by the following Chemical Formula 61 in addition to the condensed cyclic compound represented by Chemical Formula 1 as described above. may further include:

<Formula 41>

<Formula 61>

<Formula 61A> <Formula 61B>

Among the above formulas,

X ₄₁ is N-[(L ₄₂ ) _a42 -(R ₄₂ ) _b42 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₄₃ )(R ₄₄ ), Si(R ₄₃ )(R ₄₄ ), P(R ₄₃ ), P(=O)(R ₄₃ ) or C=N(R ₄₃ );

Ring A ₆₁ in Formula 61 is represented by Formula 61A;

Ring A ₆₂ in Formula 61 is represented by Formula 61B;

X ₆₁ is N-[(L ₆₂ ) _a62 -(R ₆₂ ) _b62 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₆₃ )(R ₆₄ ), Si(R ₆₃ )(R ₆₄ ), P(R ₆₃ ), P(=O)(R ₆₃ ) or C=N(R ₆₃ );

X ₇₁ is C(R ₇₁ ) or N, X ₇₂ is C(R ₇₂ ) or N, X ₇₃ is C(R ₇₃ ) or N, X ₇₄ is C(R ₇₄ ) or N, and X ₇₅ is C(R ₇₅ ) or N, X ₇₆ is C(R ₇₆ ) or N, X ₇₇ is C(R ₇₇ ) or N, and X ₇₈ is C(R ₇₈ ) or N;

Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ - a C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

n1 and n2 are each independently selected from an integer of 0 to 3;

a41, a42, a61 and a62 are each independently selected from an integer of 0 to 5;

R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ and R ₇₁ to R ₇₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br ( bromo group), -I (iodo group), 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 a salt thereof, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, 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 ) and -B(Q ₆ )(Q ₇ );

b41, b42, b51 to b54, b61, b62 and b79 are each independently selected from an integer of 1 to 3;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,

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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one; 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heterocyclic group It may be selected from a polycyclic group.

For example, in the organic light emitting device, at least one of i) the condensed cyclic compound represented by Formula 1 and ii) the first compound represented by Formula 41 and the second compound represented by Formula 61 are all; It may be included in the light emitting layer.

As another example, the light emitting layer includes a first host, a second host, and a dopant, wherein the first host includes the condensed cyclic compound represented by Formula 1, and the second host includes the Formula 41 It may include at least one of the first compound and the second compound represented by Formula 61.

The weight ratio of the first host and the second host may be selected within the range of 1:99 to 99:1, for example, 10:90 to 90:10. When the weight ratio range is satisfied, the electron-aqueous property by the first host and the hole transport property by the second host can be balanced, so that the luminous efficiency and lifespan of the organic light-emitting device can be improved.

The ring A ₆₁ is fused while sharing carbon with each of the adjacent 5-membered ring and ring A ₆₂ in Formula 61 above. The ring A ₆₂ is fused with each of the adjacent ring A ₆₁ and a 6-membered ring in the following formula 61 while sharing carbon.

According to one embodiment, X ₄₁ may be N-[(L ₄₂ ) _a42 -(R ₄₂ ) _b42 ], S or O, but is not limited thereto.

According to another embodiment, X ₆₁ may be N-[(L ₆₂ ) _a62 -(R ₆₂ ) _b62 ], S or O, but is not limited thereto.

According to another embodiment, in Formula 61, X ₇₁ is C(R ₇₁ ), X ₇₂ is C(R ₇₂ ), X ₇₃ is C(R ₇₃ ), X ₇₄ is C(R ₇₄ ), and , X ₇₅ may be C(R ₇₅ ), X ₇₆ may be C(R ₇₆ ), X ₇₇ may be C(R ₇₇ ), and X ₇₈ may be C(R ₇₈ ), but is not limited thereto.

At least two of R ₇₁ to R ₇₄ in Formula 61 may be optionally connected to each other to form a saturated or unsaturated ring (eg, benzene, naphthalene, etc.).

Meanwhile, in Formula 61, at least two of R ₇₅ to R ₇₈ may be optionally connected to each other to form a saturated or unsaturated ring (eg, benzene, naphthalene, etc.).

Specific examples of Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ , and L ₆₂ in the above formulas may be each independently selected from specific examples of L ₁ in the present specification.

According to one embodiment, in the formulas Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently

phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, Phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, p Rollylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinyl group Ren group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridi Nylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, Benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzo a carbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and

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 ₂₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, which is substituted with at least one of a heterocondensed ring group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cri Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxali nyl group, cinolinyl group and quinazolinyl group; can be selected from

According to another embodiment, in Formulas, Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ It may be selected from a -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group.

According to another embodiment, in the formulas Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently

Phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and chrysenyl group Rengi; and

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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group (biphenyl group) substituted with phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group; may be selected from, but is not limited thereto.

In the formulas, a41 represents the number of L ₄₁ , and is an integer of 0 to 5. For example, a41 may be 0, 1, or 2. When a41 is 0, *-(L ₄₁ ) _a41 -*' in Formula 41 becomes a single bond. When a41 is 2 or more, two or more L ₄₁ may be the same as or different from each other. a42 , a61 , and a62 indicate the number of L ₄₂ , L ₆₁ , and L ₆₂ , respectively, refer to the description of a41 .

n1 represents the number of Ar ₄₁ in Formula 41, and is selected from an integer of 0 to 3. According to one embodiment, n1 is 0 or 1. For example, n1 may be 0, but is not limited thereto.

For example, a41, a42, a61, and a62 in the above formulas may each independently be 0 or 1, but is not limited thereto.

Specific examples of R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ , and R ₇₁ to R ₇₉ in the above formulas may be each independently selected from specific examples of R ₁ in the present specification.

According to one embodiment, in Formulas 41 and 61, R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ and R ₇₁ to R ₇₉ 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 ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and di benzocarbazolyl group; and

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, phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo A phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, benzo which is substituted with at least one of a thiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Fluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; may be selected from, but is not limited thereto.

According to another embodiment, R ₅₁ , R ₅₃ and R ₅₄ in Formula 41 and R ₇₁ to R ₇₉ in Formula 61 may be each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydrogen 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 a salt thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ It may be selected from an alkenyl group, a C ₂ -C ₂₀ alkynyl group, and a C ₁ -C ₂₀ alkoxy group.

According to another embodiment, R ₅₁ , R ₅₃ and R ₅₄ in Formula 41 and R ₇₁ to R ₇₉ in Formula 61 may all be hydrogen.

According to another embodiment, R ₄₁ , R ₄₂ and R ₅₂ in Formula 41 and R ₆₁ and R ₆₂ in Formula 61 may be each independently represented by one of Formulas 4-1 to 4-31.

According to another embodiment, R ₄₁ , R ₄₂ and R ₅₂ in Formula 41 and R ₆₁ and R ₆₂ in Formula 61 may be each independently selected from Formulas 4-1 to 4-5 and 4-26 to 4- 31 may be displayed.

According to another embodiment, R ₄₁ , R ₄₂ and R ₅₂ in Formula 41 and R ₆₁ and R ₆₂ in Formula 61 may be each independently selected from Formulas 5-1 to 5-26, 5-56 to 5- 85, but is not limited thereto.

The first compound may be represented by one of the following Chemical Formulas 41-1 to 41-12, and the second compound may be represented by one of the following Chemical Formulas 61-1 to 61-6, but is not limited thereto.

In Formulas 41-1 to 41-12 and 61-1 to 61-6, X ₄₁ , X ₆₁ , L ₄₁ , L ₄₂ , a41 , a42 , L ₆₁ , L ₆₂ , a61 , a62 , R ₄₁ to R ₄₄ , For descriptions of b41, b42, R ₆₁ to R ₆₄ , b61, b62, R ₇₁ to R ₇₉ and b79, refer to the description herein.

According to one embodiment, the first compound represented by Formula 41 may include one of the following compounds A1 to A83, and the second compound represented by Formula 61 may include one of the following compounds B1 to B20, However, the present invention is not limited thereto.

In the organic light emitting device, for example, the light emitting layer of the organic light emitting device includes at least one of the first compound represented by Formula 41 and the second compound represented by Formula 61 in addition to the condensed cyclic compound represented by Formula 1 above. When one is further included, the balance between hole transport and electron transport among the organic light emitting devices may be more effectively achieved, and thus efficiency, luminance, and lifespan characteristics of the organic light emitting device may be improved.

A method for synthesizing the condensed cyclic compound represented by Formula 1, the first compound represented by Formula 41, and the second compound represented by Formula 61 can be easily recognized by those skilled in the art with reference to the following synthesis examples. .

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting device according to an exemplary embodiment of the present invention will be described with reference to FIG. 1 . The organic light emitting diode 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 the 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.

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, etc. there is.

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 target structure and thermal characteristics of the hole injection layer, etc., but, for example, a 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, but not limited thereto.

In the case of forming the hole injection layer by the spin coating method, the coating conditions vary 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 may include at least one of the above-described condensed cyclic compounds. For example, the hole transport layer in the hole transport region may include at least one of the above-described condensed cyclic compounds.

According to an embodiment, the hole transport region (eg, the hole transport layer in the hole transport region) includes the condensed cyclic compound represented by Chemical Formula 1, wherein L ₃ in Chemical Formula 1 is substituted or unsubstituted C selected from a ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and R ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic group It may be selected from a condensed polycyclic group.

According to another embodiment, the hole transport region (eg, the hole transport layer in the hole transport region) includes the condensed cyclic compound represented by Formula 1, wherein L ₃ in Formula 1 is,

a phenylene group, a naphthylene group, and a triphenylene group; and

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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, and a chrysenyl group substituted with at least one, a phenylene group, a naphthylene group, and a triphenylene group; is selected from

R ₃ may be selected from Formulas 4-1 to 4-5.

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

<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, 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 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 Nyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ - A phenylene group, a pentarenylene group, an indenylene group, a naphthylene group, an azulenylene group, substituted with at least one of 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, a picenylene group, a perylenylene group, and a pentacenylene group; can be selected from

In Formula 201, xa and xb may each independently represent 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 C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with one or more salts thereof;

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

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, 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, 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, a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group substituted with one or more of a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; can be selected from

According to one embodiment, the compound represented by Chemical Formula 201 may be represented by the following Chemical 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 It may be 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, a satisfactory level of 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 a cyano group-containing compound such as the following compound HT-D1, but is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

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 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 and 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.

The emission layer may include a host and a dopant. The host may include at least one of the condensed cyclic compounds represented by Formula 1 above.

For example, the host includes a condensed cyclic compound represented by Formula 1, wherein R ₃ in Formula 1 is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent ratio - It may be a condensed aromatic heteropolycyclic group.

According to an embodiment, the host includes the condensed cyclic compound represented by Formula 1, wherein R ₃ in Formula 1 may be selected from the group represented by Formulas 4-6 to 4-25.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and/or a blue light emitting layer are stacked, and thus various modifications such as emitting white light are possible. Among the red light emitting layer, the green light emitting layer, and the blue light emitting layer, the host may include at least one of the condensed cyclic compounds represented by Formula 1 above. According to one embodiment, the host in the green light emitting layer may include one or more of the condensed cyclic compound represented by Formula 1 above.

Meanwhile, in the emission layer, a host includes a first host and a second host, wherein the first host includes at least one of the condensed cyclic compounds represented by Formula 1, and the second host is represented by Formula 41 It may include at least one of the first compound and the second compound represented by Formula 61.

A dopant in the emission layer may include a fluorescent dopant that emits light according to a fluorescence emission mechanism or a phosphorescent dopant that emits light according to a phosphorescence emission mechanism.

According to an exemplary embodiment, the light emitting layer may include a host including at least one of the condensed cyclic compounds represented by Formula 1 and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 81:

<Formula 81>

In Formula 81,

M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thorium (Tm);

Y ₁ to Y ₄ are each independently carbon (C) or nitrogen (N);

Y ₁ and Y ₂ are connected through a single bond or a double bond, Y ₃ and Y ₄ are connected through a single bond or a double bond;

CY ₁ and CY ₂ are independently of each other, benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole , isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzo Thiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran or dibenzothiophene, CY ₁ and CY ₂ are optionally (optionally); linked to each other via a single bond or an organic linking group;

R ₈₁ and R ₈₂ are each independently 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 carboxyl group Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, -SF ₅ , 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 A substituted 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 aryl Oxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -B(Q ₆ )(Q ₇ );

a81 and a82 are each independently selected from an integer of 1 to 5;

n81 is selected from an integer from 0 to 4;

n82 is 1, 2 or 3;

L ₈₁ is a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand.

For the description of R ₈₁ and R ₈₂ , refer to the description of R ₁₁ in the present specification.

The phosphorescent dopant may include at least one of the following compounds PD1 to PD74, but is not limited thereto (wherein, compound PD1 is Ir(ppy) ₃ ):

Alternatively, the phosphorescent dopant may comprise the following PtOEP or compound PhGD:

The fluorescent dopant may include at least one of the following DPVBi, DPAVBi, TBPe, DCM, DCJTB, Coumarin 6 and C545T.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 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 of a hole blocking layer, an electron transport layer, and an electron injection layer.

For example, the electron transport region may have a structure of an electron transport layer, 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-mentioned 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 and ET2, 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, or 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), and magnesium-silver (Mg-Ag). It can be used as a material for forming the second electrode 19 . Alternatively, in order to obtain a top light emitting device, various modifications are possible, such as forming the transmissive second electrode 19 using ITO or IZO.

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

In the present specification, the C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, 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 at least one carbon double bond 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 means 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. In the present specification, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

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

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

In the present specification, a C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group is a carbo group having 6 to 60 carbon atoms. It refers to a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, 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 ₁ -C ₆₀ heteroaryl group refers to a monovalent group including at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. and C ₁ -C ₆₀ heteroarylene group means a divalent group including at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms do. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (here, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group is -SA ₁₀₃ (here , A ₁₀₃ represents the above C ₆ -C ₆₀ aryl group).

In the present specification, a 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 (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 1 to 60) in addition to It refers to a monovalent group including a hetero atom selected from N, O, P and S, and 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 ₁ -C ₆₀ alkylene group, the substituted C ₂ -C ₆₀ alkenylene group, the substituted C ₂ -C ₆₀ alkynylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group , substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non- At least one substituent of the condensed aromatic polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic 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, -N(Q ₁₁ ) (Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), and C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of -B(Q ₁₆ )(Q ₁₇ ) , 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 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 and 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 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 hetero condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocyclo Alkenyl group, C _{6 -C 60 aryl group, C 6 -C 60} aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group and monovalent ratio -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); can be selected from

In addition, in the present specification, Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , and Q ₃₁ to Q ₃₇ are each independently hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkyl nyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C It may be selected from a ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group.

For example, the substituted C ₁ -C ₆₀ alkylene group, substituted C ₂ -C ₆₀ alkenylene group, substituted C ₂ -C ₆₀ alkynylene group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ - C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl 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 heterocycloalke Nyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent ratio -At least one substituent of the condensed aromatic polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic 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, -N(Q ₁₁ ) (Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), and C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of -B(Q ₁₆ )(Q ₁₇ ) , C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spy Ro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group , isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phena Zinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group and imidazopyridinyl group;

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 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 heterocyclo Alkyl 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 hetero condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) And -B (Q ₂₆ ) (Q ₂₇ ) substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group , anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, tria Zinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group and at least one substituted with quinazolinyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, Heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, cry Cenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, Isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carba Zolyl group, phenanthridinyl group, acridinyl group, phenanthridinyl group Nantrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group , oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyrimidinyl group dazopyridinyl group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohepsenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthre Nyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, substituted with at least one of a phthalazinyl group, a quinoxalinyl group, a cinolinyl group and a quinazolinyl group , fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, Purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group , phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazole diary, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and It may be selected from an imidazopyridinyl group, but is not limited thereto.

In the present specification, "biphenyl group" means "a phenyl group substituted with a phenyl group".

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 a molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of compound 153

Synthesis of Intermediate A-3

2-bromo-benzo[1,??2-?? b :5,??4-?? b ']??bisbenzofuran, 114g, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 11.3g, PdCl ₂ (dppf) 0.5g and KOAc 8.8g were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. Then, 150ml of DMF was added thereto, and the mixture was heated and stirred at 100° C. for 8 hours. The resulting reactant was poured into 1000 ml of MeOH to crystallize, stirred and filtered, and the resulting solid was dissolved by heating in 500 ml of toluene. The resulting reaction product was filtered through silica, the solvent was removed so that the residual solution was 100 ml, and then added to 1 L of MeOH to crystallize and dried to obtain an intermediate A-3 (79.4 g).

Synthesis of Intermediate A-2

Intermediate A-3 1g, 1-iodo-2-nitrobenzene 0.8g, Pd(PPh ₃ ) ₄ 0.3g, and K ₂ CO ₃ 1g were placed in 20ml of THF / H ₂ O(1:1) and heated to 90℃ for 8 hours. while heating and stirring. The reaction product obtained therefrom was extracted twice using 20 ml of methylene chloride to remove moisture by adding 2 g of MgSO ₄ to the obtained extract, and then purified by silica gel column chromatography to obtain an intermediate A-2 (0.85 g).

Synthesis of Intermediate A-1

1 g of Intermediate A-2 and 2.1 g of PPh ₃ were put into 15 ml of 1,2-dichlorobenzene, and after heating and stirring for 22 hours, the solvent was distilled off. ) was obtained.

Synthesis of compound 153

Intermediate A-1 1g, 2-chloro-4,6-diphenylpyrimidine 0.95g, Pd ₂ (dba) ₃ 0.1g, NaOtBu, 0.6g were placed in a flask, vacuum was created, and a nitrogen atmosphere was created, and then tri 0.1 g of (tetra-butyl) phosphine and 15 ml of toluene were added, and the mixture was heated and stirred at 110° C. for 8 hours. With respect to the reaction product obtained therefrom, the solvent was removed under vacuum and purified by silica gel column chromatography to obtain compound 153 (1.41 g). The resulting compound was confirmed by LC-MS.

C ₄₀ H ₂₃ N ₃ O ₂ : M+ 577.19

¹ H NMR (500 MHz, CDCl3): δ, ppm 8.59(d, 1H), 8.25~8.22(m, 2H), 8.17(d, 1H), 8.04~8.02(m, 4H), 7.74~7.73 (m, 2H), 7.53~7.50(m, 1H), 7.45~7.35(m, 9H), 7.32~7.28(m,1H), 7.16~7.13(m,1H), 7.00(s,1H).

Synthesis Example 2: Synthesis of compound 154

Synthesis of Intermediate B-4

2,8-dibromodibenzo[b,d]thiophene 1.0g, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane ) 2.2 g, PdCl ₂ (dppf) 0.2 g, and KOAc 1.7 g were placed in a flask to create a vacuum environment, and a nitrogen atmosphere was created. 10.0 ml of H ₂ O was added to the reaction product obtained therefrom, and the solid obtained by stirring and filtration was washed with 50 ml of MeOH, and the remaining solid was purified by silica gel column chromatography to obtain Intermediate B-4 (1.1 g).

Synthesis of Intermediate B-3

Intermediate B-4 1g, 1-iodo-2-nitrobenzene 1.2g, Pd(PPh ₃ ) ₄ 0.3g, and K ₂ CO ₃ 1.9g were placed in 30ml of THF / H2O(1:1) and heated to 80℃ for 10 hours. It was heated and stirred. The reaction product obtained therefrom was extracted using methylene chloride, and MgSO ₄ was added to the obtained extract to remove moisture, and the resulting concentrate was purified by silica gel column chromatography to obtain an intermediate B-3 (0.81 g).

Synthesis of Intermediate B-2

1 g of Intermediate B-3 and 3.1 g of PPh ₃ were put into 12 ml of 1,2-dichlorobenzene, and after heating and stirring for 24 hours, the solvent was distilled off. The residue obtained was purified by silica gel column chromatography, and Intermediate B-2, 0.31 g got

Synthesis of Intermediate B-1

Intermediate B-2 1g, iodobenzene 0.6g, Pd ₂ (dba) ₃ 0.2g, and NaOtBu 0.6g were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. Here, 0.1 g of tri(tetra-butyl)phosphine and 15 ml of toluene were added, and the reaction product obtained by heating and stirring at 110 ° C. for 8 hours. The solvent was removed under vacuum and purified by silica gel column chromatography to purify Intermediate B-1 (0.8 g ) was obtained.

Synthesis of compound 154

1 g of Intermediate B-1, 1.1 g of 2-chloro-4,6-diphenylpyrimidine, 0.2 g of Pd ₂ (dba) ₃ , and 0.5 g of NaOtBu were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was heated and stirred at 110° C. for 8 hours. The solvent was removed under vacuum and purified by silica gel column chromatography to obtain compound 99 (0.95 g). got it The resulting compound was confirmed by LC-MS.

C ₄₆ H ₂₈ N ₄ S : M+ 668.31

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.90(d, 1H), 8.04(d, 1H), 7.93(d, 1H), 7.85(d, 1H), 7.74 (d, 1H), 7.60(s) , 2H), 7.47 (td, 2H), 7.35-7.11 (m,15H), 7.06-7.00 (m,1H), 6.80 (t, 2H), 6.58 (t, 1H).

Synthesis Example 3: Synthesis of compound 155

After adding 1 g of Intermediate B-1 to 11 ml of DMF, 0.2 g of NaH was added, followed by stirring at room temperature for 30 minutes, and then 0.9 g of 2-chloro-4,6-diphenyl-1,3,5-triazine was added. The mixture was stirred at room temperature for 8 hours. Methylene chloride was added to the obtained reaction product to dissolve the solid, washed with H ₂ O, and then concentrated by removing water using MgSO ₄ . The resulting concentrate was purified by silica gel column chromatography to obtain compound 155 (1.38 g). The resulting compound was confirmed by LC-MS.

C ₄₅ H ₂₇ N ₅ S : M+ 669.24

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.93(d, 1H), 8.03(d, 1H), 7.92(d, 2H), 7.69(q, 4H), 7.51 (td, 2H), 7.40-7.08 (m, 13H), 7.06 to 7.00 (m, 1H), 6.83 (t, 2H), 6.58 (t, 1H).

Synthesis Example 4: Synthesis of compound 156

1 g of Intermediate A-1, 0.81 g of 3-bromo-1,1'-biphenyl, 0.1 g of Pd ₂ (dba) ₃ and 0.6 g of NaOtBu were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was heated and stirred at 110° C. for 12 hours. The solvent was removed under vacuum and purified by silica gel column chromatography to obtain compound 156 (1.18 g). . The resulting compound was confirmed by LC-MS.

C ₃₆ H ₂₁ NO ₂ : M + 499.18

¹ H NMR (500 MHz, DMSO): δ, ppm 9.33 (s, 1H), 8.30 (d, 1H), 8.23 (d, 1H) 8.17-8.15 (m, 2H) 7.78 (d, 1H), 7.72 (d) , 1H), 7.64~7.36(m, 13H), 7.29~7.26(m, 1H)

Synthesis Example 5: Synthesis of compound 157

Intermediate B-2 1g, iodobenzene 1.6g, Pd ₂ (dba) ₃ 0.2g and NaOtBu, 1.01g were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was stirred for 8 hours at 110 ° C. The solvent was removed under vacuum and purified by silica gel column chromatography to obtain compound 157 (0.4 g) got it The resulting compound was confirmed by LC-MS.

C ₃₆ H ₂₂ N ₂ S : M+ 514.54

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.20~8.15(m, 2H), 8.01(d, 1H), 7.96~7.92(m, 2H), 7.87(d, 1H), 7.63 (d, 1H) , 7.51~7.28(m, 10H), 7.20~7.14(m, 2H), 7.10~7.04(m, 2H), 6.82~6.76(m, 1H)

Example 1

A glass substrate on which 70/1000/70Å of ITO/Ag/ITO was deposited as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then irradiated with ultraviolet light for 30 minutes. Then, it was cleaned by exposure to ozone and installed in a vacuum deposition apparatus.

After vacuum deposition of 2-TNATA on the anode (ITO/Ag/ITO) on the glass substrate to form a hole injection layer having a thickness of 600 Å, 4,4'-bis[N-(1-(1-) Naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited to form a hole transport layer with a thickness of 1000 Å.

Compound 153 (host) and Ir(ppy) ₃ (dopant) were co-deposited on the hole transport layer in a weight ratio of 90:10 to form an emission layer having a thickness of 250 Å.

BCP was vacuum deposited on the light emitting layer to form a 50 Å thick hole blocking layer, and then Alq ₃ was vacuum deposited on the hole blocking layer to form an electron transporting layer with a 350 Å thickness, and LiF was vacuum deposited on the electron transport layer. After forming an electron injection layer with a thickness of 10 Å, vacuum deposition of Mg and Ag at a weight ratio of 90:10 on the electron injection layer was performed to form a cathode with a thickness of 120 Å, thereby manufacturing an organic light emitting device.

Example 2, Example 3 and comparative example One

An organic light emitting diode was manufactured in the same manner as in Example 1, except that a compound as shown in Table 3 was used instead of Compound 153 as a host when the emission layer was formed.

Evaluation Example 1

The driving voltage, current density, efficiency, and luminance of the organic light emitting diodes of Examples 1 to 3 and Comparative Example 1 were supplied with power from a current voltmeter (Keithley SMU 236), and the luminance meter PR650 Spectoscan Source Measurement Unit (Product of PhotoResearch) was evaluated using , and the results are shown in Table 3 below.

host drive voltage
(V) current density
(㎃/㎠) luminance
(cd/m2) efficiency
(cd/A) Example 1 compound 153 4.1 10 5,332 54.3 Example 2 compound 154 3.7 10 4,960 43.1 Example 3 compound 155 3.5 10 4,813 48.3 Comparative Example 1 CBP 6.8 10 4,766 47.7

From Table 3, it can be seen that the organic light emitting diodes of Examples 1 to 3 have lower driving voltage, high efficiency, and higher luminance than the organic light emitting diodes of Comparative Example 1.

Example 4

An organic light emitting diode was manufactured using the same method as in Example 1, except that Compound 156 was used instead of NPB when forming the hole transport layer, and CBP was used instead of Compound 153 as a host when forming the light emitting layer.

Example 5

An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound 157 was used instead of Compound 156 when forming the hole transport layer.

Evaluation Example 2

The driving voltages of the organic light emitting diodes of Examples 4 and 5 and Comparative Example 1 were evaluated by supplying power from a current voltmeter (Keithley SMU 236), and the results are shown in Table 4 below.

hole transport layer drive voltage
(V) current density
(㎃/㎠) Example 4 compound 156 6.1 10 Example 5 compound 157 6.6 10 Comparative Example 1 NPB 6.8 10

From Table 4, it can be seen that the organic light-emitting devices of Examples 4 and 5 have a lower driving voltage than the organic light-emitting devices of Comparative Example 1.

Example 6

An organic light emitting device was manufactured using the same method as in Example 1, except that compound 155 (host) and Ir(ppy) ₃ (dopant) were co-deposited in a weight ratio of 85:15 when the emission layer was formed. .

Example 7

Example 1 above, except that Compound 155 (first host), Compound A2 (second host), and Ir(ppy) ₃ (dopant) were co-deposited in a weight ratio of 45:45:10 when the emission layer was formed. An organic light emitting device was manufactured using the same method as described above.

Evaluation Example 3

The driving voltage, current density, efficiency, and luminance of the organic light emitting devices of Examples 6 and 7 were evaluated using a luminance meter PR650 Spectoscan Source Measurement Unit (product of PhotoResearch) by supplying power from a current voltmeter (Keithley SMU 236). Thus, it is shown in Table 5. For comparison, Table 5 also shows the data of Comparative Example 1.

host drive voltage
(V) current density
(㎃/㎠) luminance
(cd/m2) efficiency
(cd/A) Example 6 compound 155
(Weight ratio of host and dopant = 85:15) 3.9 10 6,884 50.9 Example 7 compound 155 and compound A2
(weight ratio of 1:1) 3.8 10 5,662 56.7 Comparative Example 1 CBP 6.8 10 4,766 47.7

From Table 5, it can be seen that the organic light-emitting devices of Examples 6 and 7 have a lower driving voltage, higher luminance, and higher efficiency than the organic light-emitting devices of Comparative Example 1.

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

Claims (21)

delete Condensed cyclic compound represented by one of Formulas 1-1 to 1-12:
<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 1-7>

<Formula 1-8>

<Formula 1-9>

<Formula 1-10>

<Formula 1-11>

<Formula 1-12>

In Formulas 1-1 to 1-12,
X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, or C(R ₁₂ )(R ₁₃ );
X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, or O;
X ₃₁ to X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ];
i) In Formula 1-2, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
ii) In Formulas 1-1 to 1-12, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 not ],
iii) In Formula 1-4, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
iv) In Formula 1-8, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
v) In Formula 1-8, when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
vi) In Formulas 1-1 to 1-12, when X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 not ];
L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ hetero Arylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and substituted or unsubstituted divalent non-aromatic condensed heterocondensed polycyclic group (substituted or unsubstituted divalent non -aromatic condensed heteropolycyclic group);
a1 to a3, a11 and a12 are each independently selected from an integer of 0 to 5;
R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alke nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensation polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ ) (Q ₇ );
b1 to b3, b11 and b21 are each independently selected from an integer of 1 to 5;
c1 is an integer selected from 1 to 4;
i) In Formulas 1-1 and 1-3 to 1-12, when X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], a3 is one of integers from 1 to 5, and L ₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, and a substituted or unsubstituted a cyclic secondary non-aromatic condensed heteropolycyclic group;
ii) In Formula 1-2, when X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], a3 is one of integers from 1 to 5, and L ₃ is represented by Formulas 2-9 to 2-23 selected from:

In Formulas 2-9 to 2-23,
Z ₁ is a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzo It is selected from a furanyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, and a biphenyl group,
d2 is an integer from 1 to 3;
d5 is 1 or 2,
* and *' are each a binding site with a neighboring atom;
iii) In Formulas 1-1 to 1-12, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], a11 is one of integers from 1 to 5, and L ₁₁ is substituted or unsubstituted A substituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, and a substituted or unsubstituted secondary ratio - selected from the group of condensed aromatic heteropolycyclic;
said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,
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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one, 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ 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 or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non- It is selected from the aromatic heterocondensed polycyclic group. 3. The method of claim 2,
Condensed cyclic compound represented by one of the following formulas 1A-1 to 1A-12:
<Formula 1A-1>

<Formula 1A-2>

<Formula 1A-3>

<Formula 1A-4>

<Formula 1A-5>

<Formula 1A-6>

<Formula 1A-7>

<Formula 1A-8>

<Formula 1A-9>

<Formula 1A-10>

<Formula 1A-11>

<Formula 1A-12>

In Formulas 1A-1 to 1A-12, the descriptions of X ₁₁ , X ₂₁ , L ₁ to L ₃ , a1 to a3 , R ₁ to R ₇ and c1 are the same as those described in claim 2, and c2 is 1 to It is selected from an integer of 4. 3. The method of claim 2,
When the condensed cyclic compound is represented by Formula 1-2, the following Formulas 1A-2-2, 1A-2-3, 1A-2-5, 1A-2-6, 1A-2-9 to 1A-2 -11, and 1A-2-14 to 1A-2-16, and when the condensed cyclic compound is represented by Formula 1-4, the following Formulas 1A-4-2, 1A-4-3, 1A represented by one of -4-7, 1A-4-8, 1A-4-11 to 1A-4-13, and 1A-4-16 to 1A-4-18, and the condensed cyclic compound is represented by Formula 1-8 When represented as, the following formulas 1A-8-1, 1A-8-2, 1A-8-5, 1A-8-6, 1A-8-9 to 1A-8-11, 1A-8-14, and 1A-8-15, and when the condensed cyclic compound is represented by Formula 1A-11, the following Formulas 1A-11-2 to 1A-11-4, 1A-11-7, 1A-11-8 , 1A-11-12, 1A-11-13, 1A-11-17, and a condensed cyclic compound represented by one of 1A-11-18:

3. The method of claim 2,
Represented by one of Formulas 1-1 to 1-7 and 1-9 to 1-12,
In Formulas 1-1 to 1-7 and 1-9 to 1-12,
X ₁₁ and X ₂₁ are each independently O or S;
X ₁₁ is O or S and X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ];
X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] or C(R ₁₂ )(R ₁₃ ), and X ₂₁ is O or S. delete 3. The method of claim 2,
It is represented by the formula 1-2,
In Formula 1-2, X ₁₁ is O or S, and X ₂₁ is O, S or N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ]. 3. The method of claim 2,
The L ₁ to L ₃ , L ₁₁ and L ₂₁ are each independently,
phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, ace Naphthylene group (acenaphthylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrenylene), anthracenylene group (anthracenylene), fluoranxenylene group ( fluoranthrnylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene (pentaphenylene), hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinyl Ren group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene), isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, Cinnolinylene, carbazolylene, phenanthridinylene , acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofura Nylene group (benzofuranylene), thiophenylene group (thiophenylene), benzothiophenylene group (benzothiophenylene), thiazolylene group (thiazolylene), isothiazolylene group (isothiazolylene), benzothiazolylene group (benzothiazolylene), isoxazolylene group (isoxazolylene) ), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and
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 ₂₀ aryl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, substituted with at least one of a condensed heterocyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cri Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from
Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , a condensed cyclic compound selected from a cinolinyl group and a quinazolinyl group. 3. The method of claim 2,
Wherein L ₁ to L ₃ , L ₁₁ and L ₂₁ are each independently selected from the group represented by Formulas 2-1 to 2-34, a condensed cyclic compound:

In Formulas 2-1 to 2-34,
Y ₁ is O, S, S(=O), S(=O) ₂ , C(Z ₃ )(Z ₄ ), N(Z ₅ ), or Si(Z ₆ )(Z ₇ );
Z ₁ To Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenane Threnyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinoli a nyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );
wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carba Zolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxali selected from a nyl group, a cinolinyl group, and a quinazolinyl group;
d1 is an integer from 1 to 4, d2 is an integer from 1 to 3, d3 is an integer from 1 to 6, d4 is an integer from 1 to 8, d5 is 1 or 2, and d6 is an integer from 1 to 5 ego;
* and *' are binding sites with neighboring atoms, respectively. 3. The method of claim 2,
Wherein L ₁ to L ₃ , L ₁₁ and L ₂₁ are each independently one of Formulas 3-1 to 3-21, a condensed cyclic compound:

* and *' are binding sites with neighboring atoms, respectively. 3. The method of claim 2,
R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent A condensed cyclic compound selected from a non-aromatic condensed heteropolycyclic group, and -Si(Q ₃ )(Q ₄ )(Q ₅ ). 3. The method of claim 2,
i) when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], then at least one of R ₃ and R ₁₁ , and ii) X ₂₁ is N-[(L ₂₁ ) _a11 -(R ₂₁ ) ) _b11 ], at least one of R ₃ and R ₂₁ is, independently of each other, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted A condensed cyclic compound selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Condensed cyclic compound represented by one of Formulas 1-1 to 1-12:
<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 1-7>

<Formula 1-8>

<Formula 1-9>

<Formula 1-10>

<Formula 1-11>

<Formula 1-12>

In Formulas 1-1 to 1-12,
X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, or C(R ₁₂ )(R ₁₃ );
X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, or O;
X ₃₁ to X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ];
i) In Formula 1-2, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
ii) In Formulas 1-1 to 1-12, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] not,
iii) In Formula 1-4, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
iv) In Formula 1-8, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
v) In Formula 1-8, when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],
vi) In Formulas 1-1 to 1-12, when X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 not ];
L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ hetero Arylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and substituted or unsubstituted divalent non-aromatic condensed heterocondensed polycyclic group (substituted or unsubstituted divalent non -aromatic condensed heteropolycyclic group);
a1 to a3, a11 and a12 are each independently selected from an integer of 0 to 5;
R ₁ , R ₂ , R ₄ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a 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 a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted A substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ Aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted Condensed monovalent non-aromatic polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ );
R ₃ is, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl , oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyridazinyl, isoindolyl, indolyl, Indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl , phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxa Zolyl group (isobenzooxazolyl), triazolyl group (triazolyl), tetrazolyl group (tetrazolyl), oxadiazolyl group (oxadiazolyl), triazinyl group (triazinyl), dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl) , a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; and
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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si( _Q33 )( _Q34 )( _Q35 ) At least one substituted, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyridazinyl group group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group , carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, Benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothio a phenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
i) In Formula 1-2, when X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], a3 is one of integers from 1 to 5, and L ₃ is substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocyclo An alkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group selected from the following formulas 2-9 to 2-23, a substituted or unsubstituted divalent It is selected from a non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group:

In Formulas 2-9 to 2-23,
Z ₁ is a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzo It is selected from a furanyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, and a biphenyl group,
d2 is an integer from 1 to 3;
d5 is 1 or 2,
* and *' are each a binding site with a neighboring atom;
ii) In Formulas 1-1 to 1-12, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], R ₁₁ is a pyrrolyl group, a thiophenyl group, or a fura Nyl group (furanyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), thiazolyl group (thiazolyl), isothiazolyl group (isothiazolyl), oxazolyl group (oxazolyl), isoxazolyl group (isooxazolyl), pyridi Nyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), purinyl group (purinyl), quinolinyl group ( quinolinyl), isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, synolinyl Cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzo Furanyl group (benzofuranyl), benzothiophenyl group (benzothiophenyl), isobenzothiazolyl group (isobenzothiazolyl), benzooxazolyl group (benzooxazolyl), isobenzooxazolyl group, triazolyl group tetrazolyl), oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and an imidazopyrimidinyl group; and
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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoqui Nolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimi Dazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, substituted with at least one of a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, isoindoleyl group, indolyl group, Indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, Acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group , isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; is selected from
wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina selected from a jolinyl group and a quinoxalinyl group;
b1 to b3, b11 and b21 are each independently selected from an integer of 1 to 5;
c1 is an integer selected from 1 to 4;
said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,
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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one; 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ 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 or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non- It is selected from the aromatic heterocondensed polycyclic group. 3. The method of claim 2,
R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are independently of each other,
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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 and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Cenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), a triazinyl group, a dibenzofuranyl group (dibenzofuranyl), a dibenzothiophenyl group (dibenzothiophenyl), a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si( _Q33 )( _Q34 )( _Q35 ) At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, Hexasenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group , indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, Phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra a zolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and
-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;
wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, A condensed cyclic compound selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group. 3. The method of claim 2,
R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, 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 group represented by the following Chemical Formulas 4-1 to 4-31 and -Si(Q ₃ )(Q ₄ )(Q ₅ ) selected;
Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina A condensed cyclic compound selected from a zolinyl group and a quinoxalinyl group:

In Formulas 4-1 to 4-31,
Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );
Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group An 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, a pyrenyl group, a phenanthrenyl group, a fluorine group Nyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group selected from a nyl group, a quinazolinyl group, a quinoxalinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );
wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina selected from a jolinyl group and a quinoxalinyl group;
e1 is an integer from 1 to 5, e2 is an integer from 1 to 7, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is 1 or 2, and e6 is an integer from 1 to 6 , and * is a binding site with a neighboring atom. 3. The method of claim 2,
R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ 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 ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a group represented by the following Chemical Formulas 5-1 to 5-55 and -Si(Q ₃ )(Q ₄ )(Q ₅ ) selected;
Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina A condensed cyclic compound selected from a zolinyl group and a quinoxalinyl group:

One of the following compounds 1 to 167, a condensed cyclic compound:

a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode, including a light emitting layer, and including at least one type of the condensed cyclic compound of claim 2 or 13. 19. The method of claim 18,
The first electrode is an anode, the second electrode is a cathode, and the organic layer includes: i) a hole interposed between the first electrode and the light emitting layer, the hole including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer transport area; and ii) an electron transport region interposed between the emission layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. 20. The method of claim 19,
The condensed cyclic compound is included in at least one of the light emitting layer and the hole transport region, the organic light emitting device. 19. The method of claim 18,
An organic light emitting device in which the condensed cyclic compound is included in the light emitting layer, and at least one of a first compound represented by the following Chemical Formula 41 and a second compound represented by the following Chemical Formula 61 is further included in the light emitting layer:
<Formula 41>

<Formula 61>

<Formula 61A><Formula61B>

Among the above formulas,
X ₄₁ is N-[(L ₄₂ ) _a42 -(R ₄₂ ) _b42 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₄₃ )(R ₄₄ ), Si(R ₄₃ )(R ₄₄ ), P(R ₄₃ ), P(=O)(R ₄₃ ) or C=N(R ₄₃ );
Ring A ₆₁ in Formula 61 is represented by Formula 61A;
Ring A ₆₂ in Formula 61 is represented by Formula 61B;
X ₆₁ is N-[(L ₆₂ ) _a62 -(R ₆₂ ) _b62 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₆₃ )(R ₆₄ ), Si(R ₆₃ )(R ₆₄ ), P(R ₆₃ ), P(=O)(R ₆₃ ) or C=N(R ₆₃ );
X ₇₁ is C(R ₇₁ ) or N, X ₇₂ is C(R ₇₂ ) or N, X ₇₃ is C(R ₇₃ ) or N, X ₇₄ is C(R ₇₄ ) or N, and X ₇₅ is C(R ₇₅ ) or N, X ₇₆ is C(R ₇₆ ) or N, X ₇₇ is C(R ₇₇ ) or N, and X ₇₈ is C(R ₇₈ ) or N;
Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ - a C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
n1 and n2 are each independently selected from an integer of 0 to 3;
a41, a42, a61 and a62 are each independently selected from an integer of 0 to 5;
R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ and R ₇₁ to R ₇₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br ( bromo group), -I (iodo group), 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 a salt thereof, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, 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 ) and -B(Q ₆ )(Q ₇ );
b41, b42, b51 to b54, b61, b62 and b79 are each independently selected from an integer of 1 to 3;
said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of the ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,
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, 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, 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 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, -N(Q ₁₁ ) ( Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, substituted with at least one, 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 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, 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, 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, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent ratio -Aromatic heterocondensed polycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heterocyclic group selected from the polycyclic group.

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