KR102336016B1 - 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 Formula 1A or 1B:

<Formula 1A>

<Formula 1B>

<Formula 1C> <Formula 1D>

Among the above formulas,

_{Ring A 1} in Formulas 1A and 1B is represented by Formula 1C or 1D;

X ₁ is N or C-[(L ₁ ) _a1- (R ₁ ) _b1 ], X ₂ is N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ], and X ₃ is N or C -[(L ₃ ) _a3 -(R ₃ ) _b3 ], and at least one of _{X 1} to X _{3 is N;}

X ₄ is O or S;

X ₁₁ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₁₃ )(R ₁₄ ), Si(R ₁₃ )(R ₁₄ ), P(R ₁₃ ), P(=O)(R ₁₃ ) and C=N(R ₁₂ );

L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₂ - 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;

a1 to a4, a11, a12 and a21 are each independently selected from an integer of 0 to 3;

R ₁ to R ₃ , R ₅ , R ₆ and R ₁₁ to R ₁₇ 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 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 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group , substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ - 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 );

R ₄ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group;

b1 to b6 and b11 to b17 are each independently selected from an integer of 1 to 3;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₂ -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 ₂ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -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 2} -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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -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 ₂ -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 ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- 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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic fused polycyclic selected from the 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 1A or 1B:

<Formula 1A>

<Formula 1B>

_{Ring A 1} in Formulas 1A and 1B is represented by Formula 1C or 1D.

<Formula 1C> <Formula 1D>

_{Ring A 1} in Formulas 1A and 1B is fused with an adjacent 5-membered ring while sharing a carbon atom. Accordingly, the condensed cyclic compound represented by Formula 1A or 1B may be represented by one of Formulas 1A-1 to 1A-7 and 1B-1 to 1B-4:

<Formula 1A-1>

<Formula 1A-2>

<Formula 1A-3>

<Formula 1A-4>

<Formula 1A-5>

<Formula 1A-6>

<Formula 1A-7>

<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

<Formula 1B-4>

In Formulas 1A-1 to 1A-7 and 1B-1 to 1B-4, X ₁ to X ₄ , X ₁₁ , L ₁ to L ₄ , L ₁₁ , L ₁₂ , L ₂₁ , a1 to a4, a11, a12, Descriptions of a21, R ₁ to R ₆ , R ₁₁ to R ₁₇ , b1 to b6 and b11 to b17 refer to those described herein.

According to one embodiment, the condensed cyclic compound may be represented by Formula 1A-1, 1A-2, 1A-3, 1B-1, 1B-2, 1B-3 or 1B-4, but is limited thereto no.

According to another embodiment, the condensed cyclic compound may be represented by Formula 1A-1 or 1A-2, but is not limited thereto.

Formulas 1A and 1B may be represented by one of Formulas 1A(1) to 1A(4) and 1B(1) to 1B(4), but are not limited thereto:

<Formula 1A(1)>

<Formula 1A(2)>

<Formula 1A(3)>

<Formula 1A(4)>

<Formula 1B(1)>

<Formula 1B(2)>

<Formula 1B(3)>

<Formula 1B(4)>

In Formulas 1A(1) to 1A(4) and 1B(1) to 1B(4), rings A ₁ , X ₁ to X ₄ , X ₁₁ , L ₁ to L ₄ , L ₁₁ , L ₁₂ , L ₂₁ , Descriptions of a1 to a4, a11, a12, a21, R ₁ to R ₆ , R ₁₁ to R ₁₇ , b1 to b6 and b11 to b17 refer to those described herein.

In Formula 1C, X ₁₁ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R _{13 )} )(R ₁₄ ), Si(R ₁₃ )(R ₁₄ ), P(R ₁₃ ), P(=O)(R ₁₃ ) and C=N(R ₁₂ ). For example, in Formula 1C, X ₁₁ may be selected from N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S, O, and C(R ₁₃ )(R ₁₄ ), but is not limited thereto. it is not For the description of L ₁₂ , a12 , R ₁₂ to R ₁₄ and b12, refer to the bar below.

In Formulas 1A and 1B, X ₁ is N or C-[(L ₁ ) _a1- (R ₁ ) _b1 ], X ₂ is N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ], X ₃ is N or C-[(L ₃ ) _a3- (R ₃ ) _b3 ], and at least one of _{X 1} to X _{3 is N.}

For example, in Formulas 1A and 1B,

X ₁ to X ₃ are N;

X ₁ is C-[(L ₁ ) _a1- (R ₁ ) _b1 ], and X ₂ and X ₃ are N;

X ₁ is N, X ₂ is C-[(L ₂ ) _a2 -(R ₂ ) _b2 ], and X ₃ is N;

X ₁ and X ₂ are N, and X ₃ is C-[(L ₃ ) _a3- (R ₃ ) _b3 ];

X ₁ is C-[(L ₁ ) _a1- (R ₁ ) _b1 ], X ₂ is N, X ₃ is C-[(L ₃ ) _a3- (R ₃ ) _b3 ];

X ₁ is C-[(L ₁ ) _a1- (R ₁ ) _b1 ], X ₂ is C-[(L ₂ ) _a2- (R ₂ ) _b2 ], and X ₃ is N;

X ₁ may be N, X ₂ may be C-[(L ₂ ) _a2- (R ₂ ) _b2 ], and X ₃ may be C-[(L ₃ ) _a3- (R ₃ ) _b3 ].

According to an embodiment, the X ₁ is C-[(L ₁ ) _a1- (R ₁ ) _b1 ], and X ₂ and X ₃ are N; X ₁ and X ₂ may be N, and X ₃ may be C-[(L ₃ ) _a3- (R ₃ ) _b3 ], but is not limited thereto.

The _{descriptions of L 1} to L ₃ , a1 to a3 , R ₁ to R _{3 ,} and b1 to b3 refer to the bar below.

In Formulas 1A, 1B, and 1C, L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, It may be selected from a substituted or unsubstituted C ₂ -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.

For example, in Formulas 1A, 1B, and 1C, L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, ace A naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group, isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, 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 ₂ -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, quinoxalinyl group , but may be selected from a cinolinyl group and a quinazolinyl group, but is not limited thereto.

For example, in Formulas 1A, 1B, and 1C, L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ may be each independently selected from Formulas 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 or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthree Nyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl 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, 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;

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, , d6 is selected from an integer of 1 to 5, and * and *' are binding sites with neighboring atoms.

For example, in Formulas 2-1 to 2-34, *' represents a bonding site with each _{of adjacent L 1} to L ₄ , L ₁₁ , L ₁₂ and L _{21 or R 1} to R ₄ , R ₁₁ , R ₁₂ and It is a binding site with each of _{R 21 .}

According to one embodiment, in Formulas 1A, 1B, and 1C, L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ may be each independently selected from Formulas 2-1 to 2-5, 2-9 to 2- 23 and 2-34 may be selected, but is not limited thereto.

According to another embodiment, in Formulas 1A, 1B, and 1C, L ₁ to L ₄ , L ₁₁ , L ₁₂ and L ₂₁ are each independently

a phenylene group and a naphthylene 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, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxali group nyl group, biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) (the Q ₃₃ to Q ₃₅ are each independently of each other, 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, pyridi a phenylene group and a naphthylene group substituted with at least one selected from a nyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group); may be selected from, but is not limited thereto.

In Formula 1A, a1 represents _{the number of L 1} , and may be 0, 1, 2, or 3, for example, 0, 1, or 2, and as another example, may be 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 to a4, a11, a12, and a21 may be understood with reference to the description of a1 and structures of Formulas 1A, 1B, and 1C.

According to one embodiment, a1 to a4, a11, a12, and a21 in the above formula may each independently be 0, 1, or 2.

According to another embodiment, a21 in the formula may be 1, but is not limited thereto.

In Formulas 1A, 1B, and 1C, R ₁ to R ₃ , R ₅ , R ₆ , and R ₁₁ to R ₁₇ 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted a C ₂ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group a _{group, a substituted or unsubstituted C 2} -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ). Here, _{the description of Q 1} to Q ₇ will be referred to below.

In Formulas 1A and 1B, R ₄ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, A substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ - Select from a C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group do. For example, R ₄ is a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or an unsubstituted monovalent non-aromatic condensed heteropolycyclic group, but is not limited thereto.

According to one embodiment, in Formulas 1A, 1B, and 1C, R ₁₁ and R ₁₂ may be each independently selected from a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 1A, 1B and 1C, R ₁ to R ₃ , R ₅ , R ₆ and R ₁₃ to R ₁₇ 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 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 Tenyl 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, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubysenyl 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenantridinyl, 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, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group 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 , 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, phenane Tridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diary, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ), with the proviso that R ₁₃ and R ₁₄ are not -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.

In another embodiment, in Formulas 1A, 1B and 1C, R ₁ to R ₃ , R ₅ , R ₆ and R ₁₃ to R ₁₇ 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 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;

Phenyl group, naphthyl group, anthracenyl group, triphenylenyl 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, isoquinolinyl group, quinazolinyl group and quinoxalinyl 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, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, anthracenyl group, triphenylenyl 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, A phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, and chrysenyl group substituted with at least one of a quinolinyl group, an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group Group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolyl group nyl group and quinoxalinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); selected from (provided that R ₁₃ and R ₁₄ are not -Si(Q ₃ )(Q ₄ )(Q ₅ );

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, triphenylenyl group, pyrethane Nyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group , may be selected from a quinolinyl group, an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group.

Meanwhile, in Formulas 1A, 1B, and 1C, R ₄ , R ₁₁ and R ₁₂ are each independently

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, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, penta Cenyl group, rubysenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Lidinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary, imidazopyridinyl group and imidazopyrimidinyl; 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, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubysenyl 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenantridinyl, 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, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group 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 , 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, phenane Tridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diary, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and 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 It may be selected from a jolinyl group and a quinoxalinyl group.

According to another embodiment, in Formulas 1A, 1B and 1C,

The R ₁ to R ₃ , R ₅ , R ₆ and R ₁₃ to R ₁₇ 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 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;

Formulas 4-1 to 4-31 (eg, Formulas 4-1 to 4-3 and 4-6 to 4-13); and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); selected from (provided that R ₁₃ and R ₁₄ are not -Si(Q ₃ )(Q ₄ )(Q ₅ );

The R ₄ , R ₁₁ and R ₁₂ may be each independently selected from the following Chemical Formulas 4-1 to 4-31 (eg, Chemical Formulas 4-1 to 4-3 and 4-6 to 4-13). , 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 Acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthree Nyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group , an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

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, triphenylenyl group, pyrethane Nyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group , is selected from a quinolinyl group, an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group;

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

According to another embodiment, the R ₁ to R ₃ , R ₅ , R ₆ and R ₁₃ to R ₁₇ 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 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 salt thereof;

a phenyl group and a naphthyl 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 a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group substituted with at least one of a phenyl group and a naphthyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); (provided that R ₁₃ and R ₁₄ are not -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 selected from an alkoxy group, a phenyl group, and a naphthyl group);

The R ₄ , R ₁₁ and R ₁₂ are independently of each other,

a phenyl group and a naphthyl 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 a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group substituted with at least one of a phenyl group and a naphthyl group; may be selected from, but is not limited thereto.

According to another embodiment, the R ₅ , R _{6 ,} and R ₁₅ to R ₁₇ may all be hydrogen, but are not limited thereto.

In Formulas 1A and 1B, b1 represents _{the number of R 1} , and may be selected from an integer of 1 to 3. For example, b1 may be 1 or 2. Specifically, 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 b6 and b11 to b17 may be understood with reference to the description of b1 and structures of Formulas 1A, 1B, 1C, and 1D.

According to one embodiment, in the present specification, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₂ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₂ - C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group 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 ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -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 2} -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed polycyclic group At least one of the substituents of

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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -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 ₂ -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 ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- 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 ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic fused polycyclic can be selected from a group.

The condensed cyclic compound may be one of the following compounds 1 to 824, but is not limited thereto:

In the fused-ring compound represented by Formula 1A or 1B, R ₄ is "a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or an unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non- aromatic heterocondensed polycyclic group".

That is, R ₄ in Formula 1A or 1B necessarily has a ring structure. Accordingly, the condensed cyclic compound represented by Formula 1A or 1B may be chemically and structurally stabilized, and may have a substantially spherical molecular structure. Accordingly, the condensed cyclic compound represented by Formula 1A or 1B may have excellent thermal stability, and thus, the deposition temperature may be improved, and thus the efficiency and lifespan of the organic light emitting device employing the condensed cyclic compound may be improved. and processability may be improved in manufacturing the organic light emitting device.

In addition, in Formulas 1A and 1B, since both the “A” group and the “carbazole-based” group are bonded to the “nitrogen-containing 6-membered ring” (see Formulas 1A′ and 1B′ below), hole injection, hole transport and electron injection Both and electron transport may be smoothly performed and may have a substantially spherical molecular structure. Accordingly, the condensed cyclic compound may have excellent charge transport ability and thermal stability at the same time, and an organic light emitting device employing the same may have an increase in luminous efficiency, a decrease in driving voltage, and a long lifespan.

<Formula 1A'>

<Formula 1B'>

A method for synthesizing the condensed cyclic compound represented by Formula 1A or 1B can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Accordingly, the condensed cyclic compound represented by Formula 1A or 1B may be suitable for use as a host of an organic layer of an organic light emitting device, for example, a light emitting layer among the organic layers. 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 1A or 1B.

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

The condensed cyclic compound represented by Formula 1A or 1B 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 1A or 1B may be included in the emission layer. In this case, 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 at least one condensed cyclic compound" means "(organic layer) belongs to one type of condensed cyclic compound belonging to the scope of Chemical Formula 1A or 1B, or belonging to the scope of Chemical Formula 1A or 1B. may include two or more different condensed cyclic compounds.”

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 may be present in the same layer (for example, both the compound 1 and the compound 2 may be present in the emission layer) or may be present in different layers.

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.

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 by, for example, 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, and the like. have.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the 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 in the range, 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 is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-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:

<Formula 201>

<Formula 202>

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

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

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, C ₂ -C ₁₀ heterocycloalkyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - 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, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group substituted with one or more of a _{C 1} -C ₁₀ alkyl group and a C ₁ -C _{10 alkoxy group;} may be one of, but is not limited thereto.

In Formula 201, R ₁₀₉ is a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof; a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C _{20 alkoxy group;} can be one of

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

<Formula 201A>

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

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

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

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

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane quinone derivatives such as phosphorus (F4-TCNQ); 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 1A or 1B.

The host may include at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, and TCP, in addition to the condensed cyclic compound represented by Formula 1 above:

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 the condensed cyclic compound represented by Formula 1 above. According to one embodiment, the host in the green light emitting layer may include the condensed cyclic compound represented by Formula 1A or 1B.

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 embodiment, the emission layer may include a host including a condensed cyclic compound represented by Formula 1A or 1B and a phosphorescent dopant. The phosphorescent dopant may include an organometallic complex including a transition metal (eg, iridium (Ir), platinum (Pt), osmium (Os), rhodium (Rh), etc.).

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

<Formula 81>

In Formula 81,

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

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

Y ₁ and Y ₂ are connected by a single bond or a double bond, Y ₃ and Y ₄ are connected by 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 selected from thiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran and dibenzothiophene, and CY ₁ and CY ₂ are optionally ), linked to each other through 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -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 ₂ -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 );

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

n81 is an integer from 0 to 4;

n82 is 1, 2 or 3;

L ₈₁ is selected from a monovalent organic ligand, a divalent organic ligand and a trivalent organic ligand;

In Formula 81, _{the bond between Y 1} and Y ₂ and the bond between Y ₃ and Y ₄ are, each independently, a single bond or a double bond.

For the description of R ₈₁ and R ₈₂ , refer to the description _{of R 5 in the present specification.}

The phosphorescent dopant may include at least one of the following compounds PD1 to PD74, but is not limited thereto:

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 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

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

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

The electron transport region may include at least one 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-described 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), magnesium-silver (Mg-Ag), etc. 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 the present invention 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. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

In the present specification, the C ₂ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P 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 ₂ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₂ -C _{10 heterocycloalkyl group.}

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

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

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

In the present specification, the C ₂ -C ₆₀ heteroaryl group 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 2 to 60 carbon atoms. and C ₂ -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 2 to 60 carbon atoms do. Specific examples of the C ₂ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₂ -C ₆₀ heteroaryl group and the C ₂ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ is 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, two or more rings are condensed with each other, and carbon as a ring-forming atom (eg, carbon number may be 2 to 60) in addition to It refers to a monovalent group including a hetero atom selected from N, O, P and S, and the entire molecule has non-aromaticity. 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.

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

[Example]

Synthesis Example 1: Synthesis of compound 813

Synthesis of Intermediate B

Intermediate B

44.0 g (224.3 mmol) of Intermediate A, 126.9 g (224.3 mmol) of acetophenone, and 9.0 g (224.3 mmol) of sodium hydroxide in 670 mL of ethanol in a 1000 mL round flask, under a nitrogen stream for 2 hours while stirring at room temperature. The crystallized solid in the resulting mixture was filtered to obtain Intermediate B (59.2. g, 88.0% yield). The results of elemental analysis of the obtained intermediate B are as follows.

calcd. C ₂₁ H ₁₄ O ₂ : C, 84.54; H, 4.73; O, 10.73; found: C, 84.51; H, 4.75; O, 10.71;

Synthesis of Intermediate C

Intermediate C

In a 1000 mL round flask, 13.0 g (106.2 mmol) of Intermediate B, 30.0 g (127.4 mmol) of 3-bromobenzimidamide and 8.5 g (212.3 mmol) of sodium hydroxide in ethanol 500 ml was added, and the mixture was heated under a nitrogen stream for 15 hours and refluxed. After filtering the crystallized solid in the resulting mixture, the solid was stirred with water and then filtered. The crystallized solid was stirred again using ethanol and filtered to obtain Intermediate C (23.8 g, yield of 47%). The results of elemental analysis of the obtained intermediate C are as follows.

calcd. C ₂₈ H ₁₇ BrN ₂ O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35; found C, 70.43; H, 3.60; Br, 16.72; N, 5.85; O, 3.36;

Synthesis of compound 813

compound 813

In a 500 mL round flask, 23.8 g (49.9 mmol) of intermediate C, 7.0 g (41.6 mmol) of 9H-carbazole, 8.0 g (83.1 mmol) of sodium t-butoxide, 3.8 g of _{Pd(dba) 2 (} 4.2 mmol) and tri-t-butylphosphine 4.2 mL (8.3 mmol) (50% in toluene) were placed in 166.2 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized from methanol to obtain compound 813 (11.7 g, 50%) yield) was obtained. Elemental analysis results and NMR analysis results of the obtained compound 813 are as follows.

calcd. C ₄₀ H ₂₅ N ₃ O: C, 85.24; H, 4.47; N, 7.46; O, 2.84; found C, 85.22; H, 4.46; N, 7.47; O, 2.83;

300 MHz (CDCl ₃ , ppm): 8.960 (m, 1H), 8.865 (m, 2H), 8.657 (dd, 1H), 8.359 (dd, 2H), 8.196 (d, 2H), 8.081 (dd, 1H) , 7.999 (d, 1H), 7.816 (t, 1H), 7.659 to 7.727 (m, 2H), 7.381 to 7.601 (m, 10H), 7.316 (t, 2H)

Synthesis Example 2: Synthesis of compound 814

compound 814

In a 500 mL round flask, 15.0 g (31.4 mmol) of Intermediate C, 9.7 g (37.7 mmol) of 5H-benzofuro[3,2-c]carbazole, sodium t- Butoxide 6.0 g (62.9 mmol), Pd(dba) ₂ 2.9 g (3.1 mmol) and tri-t-butylphosphine 3.1 mL (6.3 mmol) (50% in toluene) were added to 125.7 mL xylene and 15 under a nitrogen stream. It was heated to reflux for an hour. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to obtain compound 814 (11.8 g, 57 %) was obtained. Elemental analysis results and NMR analysis results of the produced compound 814 are as follows.

calcd. C ₄₆ H ₂₇ N ₃ O ₂ : C, 84.51; H, 4.16; N, 6.43; O, 4.89; found C, 84.49; H, 4.17; N, 6.44; O, 4.87

300 MHz (CDCl ₃ , ppm): 9.023 (t, 1H), 8.905~8.959 (m, 2H), 8.797 (dd, 1H), 8.666 (dd, 1H), 8.392 (m, 2H), 8.110 (dd, 1H), 8.012 (m, 3H), 7.684~7.884 (t, 4H), 7.362~7.627 (m, 12H)

Synthesis Example 3: Synthesis of compound 815

Synthesis of Intermediate D

Intermediate D

In a 1000 mL round flask, 30.0 g (152.9 mmol) of Intermediate A, 30.4 g (152.9 mmol) of 1- (3-bromophenyl) ethanone, and sodium hydroxide 6.1 g (152.9 mmol) was placed in 458.7 mL of ethanol and stirred at room temperature for 2 hours under a nitrogen stream. The resulting mixture was filtered through a crystallized solid to obtain an intermediate D (46.2 g, yield of 80.0%). The results of elemental analysis of the obtained intermediate D are as follows.

calcd. C ₂₁ H ₁₃ BrO ₂ : C, 66.86; H, 3,47; Br, 21.18; O, 8.48; found C, 66.83; H, 3,45; Br, 21.17; O, 8.49;

Synthesis of Intermediate E

Intermediate E

In a 2000 mL round flask, 80.3 g (212.9 mmol) of Intermediate D, 40.0 g (255.4 mmol) of benzimidamide, and 17 g (425.7 mmol) of sodium hydroxide were placed in 1000 ml of ethanol under a nitrogen stream. It was heated to reflux for 15 hours. After filtering the crystallized solid in the resulting mixture, the solid is stirred with water and filtered. The crystallized solid was stirred again with ethanol and filtered to give Intermediate E (45.8 g, 45% yield). The results of elemental analysis of the obtained Intermediate E are as follows.

calcd. C ₂₈ H ₁₇ BrN ₂ O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35; found C, 70.44; H, 3.61; Br, 16.71; N, 5.84; O, 3.35;

Synthesis of compound 815

compound 815

Intermediate E 34.3 in a 500 mL round flask. g (71.8 mmol), 10.0 g (60.0 mmol) of 9H-carbazole, 11.5 g (119.6 mmol) of sodium t-butoxide, 5.5 g (6.0 mmol) of _{Pd(dba) 2 and tri-t-butyl} Phosphine 2.9 mL (12.0 mmol) (50% in toluene) was placed in 239.2 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and then recrystallized with methanol to obtain compound 815 (22.2 g, 66 %) was obtained. Elemental analysis results and NMR analysis results of the obtained compound 815 are as follows.

calcd. C ₄₀ H ₂₅ N ₃ O: C, 85.24; H, 4.47; N, 7.46; O, 2.84; found C, 85.21; H, 4.47; N, 7.48; O, 2.86;

300 MHz (CDCl ₃ , ppm): 8.905 (s, 1H), 8.745 (m, 3H), 8.635 (t, 1H), 8.473 (tt, 1H), 8.208 (d, 2H), 8.120 (dd, 1H) , 8.016 (d, 1H), 7.802~7.885 (m, 2H), 7.317~7.600 (m, 13H)

Synthesis Example 4: Synthesis of compound 816

compound 816

In a 500 mL round flask, 19.0 g (56.0 mmol) of Intermediate E, 12.0 g (46.6 mmol) of 5H-benzofuro[3,2-c]carbazole, sodium t- Butoxide 6.7 g (70.0 mmol), Pd(dba) ₂ 1.3 g (1.4 mmol) and tri-t-butylphosphine 2.1 mL (4.2 mmol) (50% in toluene) were added to 182.9 mL xylene and 15 under a nitrogen stream. It was heated to reflux for an hour. The resulting mixture was added to 1000 mL of methanol and the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to obtain compound 816 (14.7 g, 48 %) was obtained. Elemental analysis results and NMR analysis results of the obtained compound 816 are as follows.

calcd. C ₄₆ H ₂₇ N ₃ O ₂ : C, 84.51; H, 4.16; N, 6.43; O, 4.89; found C, 84.53; H, 4.18; N, 6.42; O, 4.87

300 MHz (CDCl ₃ , ppm): 8.903 (s, 1H), 8.739 (d, 3H), 8.641 (t, 2H), 8.506 (d, 1H), 8.096 (d, 1H), 7.976 (m, 3H) , 7.868 (m, 2H), 7.763 (d, 1H), 7.347~7.634 (m, 13H)

Evaluation Example 1: Evaluation of HOMO, LUMO and triplet (T1) energy levels of compounds

The HOMO, LUMO and triplet (T1) energy levels for compounds 813 to 824 were evaluated using the DFT method of the Gaussian program (structure optimized at the B3LYP, 6-31G(d,p) level) Table 1 below shown in

compound No. HOMO (eV) LUMO (eV) T ₁ energy level (eV) 813 -5.236 -1.880 2.994 815 -5.355 -1.802 3.096 817 -5.252 -1.877 3.002 819 -5.435 -1.894 3.089 814 -5.150 -1.894 2.9 816 -5.344 -1.909 3.02 820 -5.303 -1.925 2.959 818 -5.139 -1.885 2.904 821 -5.188 -1.893 2.945 822 -5.350 -1.934 2.997 823 -5.206 -1.897 2.951 824 -5.394 -1.913 3.063

Then, according to the method of Table 2, the HOMO, LUMO, S1 energy level and T1 energy level of compounds 813 to 816 were evaluated, and the results are shown in Table 3.

HOMO ENERGY LEVEL EVALUATION METHOD Each compound _{was diluted in CHCl 3} to a concentration of 1x10 ^-5 M, and after measuring the UV absorption spectrum at room temperature using a Shimadzu UV-350 Spectrometer, the edge of the absorption spectrum Calculate the HOMO energy level using the optical band gap (Eg) from How to evaluate LUMO energy levels Cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NClO ₄ / solvent: CH ₂ Cl ₂ / electrode: three-electrode system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)) After obtaining the potential (V)-current (A) graph of each compound, the LUMO energy level of each compound is calculated from the reduction onset of the graph T1 Energy Level Assessment Method A mixture of toluene and each compound (1mg of each compound is dissolved in 3cc of toluene) is put in a quartz cell, placed in liquid nitrogen (77K), and the photoluminescence spectrum is measured using a photoluminescence measuring instrument, and the The T1 energy level is calculated by analyzing only the peaks observed only at low temperature compared to the luminescence spectrum.

compound No. HOMO (eV) LUMO (eV) T1 energy level (eV) 813 -5.432 -1.901 2.994 815 -5.665 -1.972 3.096 814 -5.451 -1.998 2.9 816 -5.643 -1.942 3.02

From Tables 1 and 3, it can be seen that the condensed cyclic compound has electrical properties suitable for use as a material for an organic light emitting device.

Evaluation Example 2: Evaluation of the thermal properties of the synthesized compound

For each of compounds 813 to 816, thermal analysis using TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) (N ₂ atmosphere, temperature section: room temperature to 800° C. (10° C./min) - TGA, 400° C. at room temperature Until-DSC, Pan Type: Pt Pan in Disposable Al Pan (TGA) , Disposable Al pan (DSC)) were performed, and the results are shown in Table 4. According to Table 4, it can be confirmed that the synthesized compounds 813 to 816 have excellent thermal stability.

compound No. Tc(℃) Tm(℃) Tg(℃) 813 - - 101.21 815 218.72 241.72 102.57 814 - 312.38 - 816 - - 139.38

Example One

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

On the ITO electrode, m-MTDATA was vacuum deposited at a deposition rate of 1 Å/sec to form a hole injection layer having a thickness of 600 Å, and the α-NPB was vacuum deposited on the hole injection layer at a deposition rate of 1 Å/sec to a thickness of 300 Å. of the hole transport layer was formed. Then, Ir(ppy) ₃ (dopant) compound 813 (host) was co-deposited on the hole transport layer at a deposition rate of 0.1 Å/sec and 1 Å/sec, respectively, to form an emission layer having a thickness of 400 Å. BAlq was vacuum deposited on the light emitting layer at a deposition rate of 1 Å/sec to form a hole blocking layer with a thickness of 50 Å, and then Alq ₃ was vacuum deposited on the hole blocking layer to form an electron transport layer with a thickness of 300 Å. LiF 10 Å (electron injection layer) and Al 2000 Å (cathode) were sequentially vacuum-deposited on the electron transport layer to fabricate an organic light emitting device.

Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 815 was used instead of Compound 813 as a host when the emission layer was formed.

Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 814 was used instead of Compound 813 as a host when the emission layer was formed.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 816 was used instead of Compound 813 as a host when the emission layer was formed.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 813 as a host when the emission layer was formed.

<Compound A>

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 813 as a host when the emission layer was formed.

<Compound B>

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C was used instead of Compound 813 as a host when the emission layer was formed.

<Compound C>

Evaluation Example 2: Evaluation of characteristics of organic light emitting devices

For each of the organic light emitting devices manufactured in Examples 1 to 4 and Comparative Examples 1 to 3, a change in current density, change in luminance, and luminous efficiency according to voltage were measured. Specific measurement methods are as follows, and the results are shown in Table 5 below:

(1) Measurement of change in current density according to voltage change

For the manufactured organic light emitting device, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.

(2) Measurement of luminance change according to voltage change

For the manufactured organic light emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and results were obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd/A) of ^{the same current density (10 mA/cm 2} ) was calculated using the luminance, current density, and voltage measured from (1) and (2) above.

host dopant Driving
Voltage
(V) current efficiency
(cd/A) luminance
(cd/m ² ) Example 1 compound 813 Ir(ppy) ₃ 3.7 40.3 3500 Example 2 compound 815 Ir(ppy) ₃ 3.4 46.2 3500 Example 3 compound 814 Ir(ppy) ₃ 4.1 36.1 3500 Example 4 compound 816 Ir(ppy) ₃ 3.8 33.8 3500 Comparative Example 1 compound A Ir(ppy) ₃ 4.4 32.6 3500 Comparative Example 2 compound B Ir(ppy) ₃ 4.3 31.5 3500 Comparative Example 3 compound C Ir(ppy) ₃ 4.2 32.9 3500

From Table 5, it can be seen that the organic light-emitting devices of Examples 1 to 4 have a lower driving voltage, high efficiency, and higher luminance than the organic light-emitting devices of Comparative Examples 1 to 3.

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

Claims (16)

Condensed cyclic compound represented by one of the following formulas 1B-1 to 1B-4:
<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

<Formula 1B-4>

In Formulas 1B-1 to 1B-4, X ₁ is N, X ₂ is N, X ₃ is N,
In Formulas 1B-1 to 1B-4, X ₄ is O or S,
In Formulas 1B-1 to 1B-4, L ₄ , L ₁₁ and L ₂₁ are each independently a group represented by one of Formulas 2-1, 2-2, and 2-34,

In Formulas 1B-1 to 1B-4, a4 and a11 are 1, a21 is 0 or 1,
In Formulas 1B-1 to 1B-4, 2-1, 2-2, and 2-34, R ₄ , R ₅ , R ₆ , R ₁₁ , R ₁₅ , R ₁₇ and Z ₁ are each independently
Hydrogen;
heavy hydrogen;
C ₁ -C ₂₀ alkyl group; or
phenyl group;
ego,
In Formulas 1B-1 to 1B-4, b4 and b11 are 1,
In Formulas 1B-1 to 1B-4, b5, b6, b15, and b17 are each independently selected from an integer of 1 to 3,
In Formulas 2-1, 2-2, and 2-34, d1 is selected from an integer of 1 to 4,
In Formulas 2-1, 2-2, and 2-34, * and *' are binding sites with neighboring atoms, respectively. According to claim 1,
A condensed cyclic compound, which is one of the following compounds:

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 condensed cyclic compound of claim 1 or 2;
Including, an organic light emitting device. 4. The method of claim 3,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer is
i) a hole transport region interposed between the first electrode and the emission layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and
i) 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;
Including, an organic light emitting device. 4. The method of claim 3,
The condensed cyclic compound is included in the light emitting layer, an organic light emitting device. 6. The method of claim 5,
An organic light emitting device, wherein the light emitting layer further comprises an organometallic compound represented by the following Chemical Formula 81:
<Formula 81>

in Formula 81
M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thorium (Tm);
Y ₁ to Y ₄ are each independently carbon (C) or nitrogen (N);
Y ₁ and Y ₂ are connected by a single bond or a double bond, Y ₃ and Y ₄ are connected by 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 selected from thiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran and dibenzothiophene, and CY ₁ and CY ₂ are optionally ), linked to each other through 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -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 ₂ -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 );
a81 and a82 are each independently selected from an integer of 1 to 5;
n81 is an integer from 0 to 4;
n82 is 1, 2 or 3;
L ₈₁ is selected from a monovalent organic ligand, a divalent organic ligand and a trivalent organic ligand;
In Formula 81, _{the bond between Y 1} and Y ₂ and the bond between Y ₃ and Y ₄ are, each independently, a single bond or a double bond. delete delete delete delete delete delete delete delete delete delete

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