KR20170087562A - Condensed-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

A condensed ring compound and an organic light emitting device containing the same are disclosed.

Description

FIELD OF THE INVENTION The present invention relates to a condensed ring compound and an organic light emitting device including the condensed ring compound.

A condensed ring compound and an organic light emitting device containing the same.

The organic light emitting device is a self light emitting type device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-coloring.

A hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode in the organic light emitting device. Lt; / RTI > structure. The holes injected from the first electrode migrate to the light emitting layer via the hole transporting region and electrons injected from the second electrode migrate to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

A novel condensed cyclic compound and an organic light emitting device containing the same.

According to an aspect, there is provided a condensed ring compound represented by the following formula (1): < EMI ID =

≪ Formula 1 >

≪ Formula 2A >

(2B)

≪ Formula 2C >

≪ Formula 10 >

Of the above formulas (1), (2A), (2C) and (10)

A ₁ is selected from the group represented by the above formulas (2A) to (2C), n 1 is selected from integers from 1 to 3,

X ₁ is N - is selected from, O, S and _{C (R 14) (R 15} ), - [(Ar 11) b11 (L 11) a11]

The B ₂ ring, the B ₃ ring and the B ₄ ring are condensed with each other,

The B ₁ ring and the B ₄ ring are each independently selected from a C ₆ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ hetero aromatic ring,

The B ₂ ring is selected from C ₇ -C ₆₀ aromatic rings and C ₁ -C ₆₀ heteroaromatic rings,

It is selected from, O, S and _{C (R 16) (R 17} ), B 3 doedoe ring represented by the formula 10, X ₂ is _{N - - [(Ar 12)} b12 (L 12) a12]

L ₁ , L ₂ , L ₁₁ and L ₁₂ each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ hetero Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non- aromatic condensed heteropolycyclic group,

a1, a2, a11 and a12 are each independently selected from the integers of 0 to 3,

Ar ₁ , Ar ₁₁ and Ar ₁₂ are, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted aryl group, Aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups,

b1, b11 and b12 are independently selected from integers from 1 to 5,

R ₁ to R ₈ and R ₁₄ to R ₁₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, 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 alkenyl group, C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted a C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 T Substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic group Ring _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 1) (Q 2), -B (Q 1) (Q 2), -C (= O) (Q 1) , -S (= O) ₂ (Q ₁ ) and -P (= O) (Q ₁ ) (Q ₂ )

R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, 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, a substituted Or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ Substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio groups, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ), -B (Q ₁ ) (Q ₂ ), Selected from _{-C (= O) (Q 1} ), -S (= O) 2 (Q 1) , and _{-P (= O) (Q 1} ) (Q 2) and,

c11 to c13 are each independently selected from an integer of 0 to 4,

* Is the binding site with neighboring atoms,

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ A substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ hetero A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic group selected from the substituent group of the condensed polycyclic group enemy Figure one,

Deuterium (-D), -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine group Division, C ₁ -C ₆₀ alkyl, C ₂ - A C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 11) (Q 12 _{), -B (Q 11) (} Q 12), -C (= O) (Q 11), -S (= O) 2 (Q 11) and _{-P (= O) (Q 11} ) (Q 12) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group , A C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- aromatic condensed polycyclic heterocyclic _{group, -Si (Q 21) (Q} 22) (Q 23), -N (Q 21) (Q 22), -B (Q 21) (Q 22), -C (= O) _{(Q 21), -S (=} O) 2 (Q 21) and _{-P (= O) (Q 21} ) (Q 22) from the at least one selected substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ come heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl tea, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic Condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And

_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 31) (Q 32), -B (Q 31) (Q 32), -C (= O) (Q 31), -S (= O) ₂ (Q ₃₁ ) and -P (= O) (Q ₃₁ ) (Q ₃₂ );

≪ / RTI >

Wherein Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, 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 ₆₀ alkoxy group, nitro group, amidino group, hydrazino group, hydrazino group, Substituted with a C ₁ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group or a C ₁ -C ₆₀ alkyl group C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group, a terphenyl group, a C ₁ -C ₆₀ heteroaryl group, a C ₁ -C ₆₀ alkyl group substituted with a C ₁ -C ₆₀ alkyl group, It is selected from a condensed polycyclic aromatic heterocyclic group-C ₆₀ heteroaryl group, a C ₆ C ₁ -C ₆₀ heteroaryl group, a monovalent non-substituted with -C ₆₀ aryl-fused polycyclic aromatic groups, and monovalent ratio.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one kind of condensed ring compound as described above.

The organic light emitting device including the condensed cyclic compound may have high efficiency and long life.

1 to 4 are schematic views each showing a structure of an organic light emitting device according to an embodiment.

The condensed ring compound is represented by the following formula (1): < EMI ID =

≪ Formula 1 >

≪ Formula 2A >

(2B)

≪ Formula 2C >

≪ Formula 10 >

X ₁ of Formula 1 is N - is selected from, O, S and _{C (R 14) (R 15} ) - [(Ar 11) b11 (L 11) a11]. Here, the descriptions of L ₁₁ , a11, Ar ₁₁ , b ₁₁ , R ₁₄ and R ₁₅ are as described in this specification. For example, X ₁ can be selected from O, S, and C (R ₁₄ ) (R ₁₅ ). According to one embodiment, X < ₁ > can be O or S.

Wherein A ₁ is selected from the group of the formulas (2A) to (2C), and n 1 is selected from an integer of 1 to 3. n ₁ represents the number of A ₁ , and when n ₁ is 2 or more, 2 or more A _{1 s} are the same or different from each other. According to one embodiment, n1 can be 1 or 2, or 1, but is not limited thereto.

The B ₂ ring, the B ₃ ring and the B ₄ ring in the above formulas (2A) to (2C) are condensed with each other.

The B ₁ and B ₄ rings in the above formulas (2A) to (2C) are independently selected from a C ₆ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ hetero aromatic ring.

For example, the B < _{1 >} ring and the B < ₄ > ring may independently of each other be selected independently of one another from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, quinoxaline, quinazoline, . For example, the A ₁ ring and the A ₂ ring may be independently selected from benzene and naphthalene. According to one embodiment, the B ₁ and B ₄ rings may be benzene, but are not limited thereto.

The B ₂ ring in the above formulas (2A) to (2C) is selected from a C ₇ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ hetero aromatic ring.

For example, the B ₂ ring can be selected from the group consisting of naphthalene, heptalene, phenalene, phenanthrene, anthracene, triphenylene, pyrene, But are not limited to, chrysene, naphthacene, picene, perylene, pentaphene, quinoline, isoquinoline, quinoxaline, quinazoline, cinanol, naphthyridine, Phenanthroline. ≪ / RTI > For example, the B < ₂ > ring may be naphthalene, but is not limited thereto.

From, O, S and _{C (R 16) (R 17} ) Formula 2A to 2C of the B ₃ ring doedoe represented by Formula 10, X ₂ is _{N - - [(Ar 12)} b12 (L 12) a12] Is selected. Here, the description of L ₁₂ , a ₁₂ , Ar ₁₂ , b ₁₂ , R ₁₆ and R ₁₇ is as described in this specification. According to one embodiment, X < ₂ > can be O or S.

L ₁ , L ₂ , L ₁₁ and L ₁₂ each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ hetero Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non- aromatic condensed heteropolycyclic group.

For example, L ₁ , L ₂ , L _11, and L ₁₂ , independently of each other,

A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , Anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, and the like. , Perylene, perylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, obarenylguanene, Ovalenylene, pyrrolylene, isoindolinone, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, thiophenylene, thiophenylene, isoxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, isoindolylene, isoindolylene, And examples thereof include indole derivatives such as indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinyl And examples thereof include phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, phenanthridinylene, ), Acridinylene group (acr and isocyanates such as isobenzothiazolylene, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, Benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzoyl, and the like. A dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazoylene group, an imidazopyridinylene group and an imidazopyrimidinylene group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, Cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylthiophenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, , A pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, A furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group , A naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, , An isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), a substituted or unsubstituted phenylene group, a substituted or unsubstituted phenylene group, an imidazopyrimidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, , Indenylene group, naphthylene group, azulenylene group, heptalenyl A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, And examples thereof include a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, An isoindolylene group, an indolylene group, an indazolylene group, a prolinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthaloylphenylene group, a phenanthrene group, Naphthylidene group, quinoxalinylene group, , A quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a cyclopentadienyl group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, And examples thereof include a benzoimidazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, a benzooxazolylene group, an isobenzoxazolanylene group, a triazololylene group, a tetrazolylene group, an oxadiazoleisonylene group, a triazienylene group, a dibenzofuranylene group, a dibenzothiophenylene group, , Dibenzocarbazolylene group, thiadiazoylene group, imidazopyridinylene group and imidazopyrimidinylene group; ≪ / RTI >

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group

As another example, L ₁ , L ₂ , L ₁₁ and L ₁₂ may be independently selected from the group consisting of the following formulas (3-1) to (3-41)

Of the above-mentioned formulas (3-1) to (3-41)

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

Z ₁ to Z ₇ are independently from each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-non-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group , Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , it is selected from the dibenzo furanoid group, a dibenzo-thio group, a triazinyl group, a benzoimidazol group, a phenanthryl group and a trolley _{-Si (Q 31) (Q 32} ) (Q 33),

Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,

d2 is 1 or 2,

d3 is selected from integers from 1 to 3,

d4 is selected from integers from 1 to 4,

d5 is selected from an integer of 1 to 5,

d6 is selected from integers from 1 to 6,

d8 is selected from integers from 1 to 8,

* And * are binding sites with neighboring atoms.

According to one embodiment, L ₁ , L ₂ , L ₁₁ and L ₁₂ may be independently selected from the group consisting of the following formulas (4-1) to (4-35)

In the above formulas (4-1) to (4-35), * and * are binding sites with neighboring atoms.

A1, a2, a11, and a12 in the above formulas (1) and (10) are independently selected from integers of 0 to 3; a1 represents the number of L ₁ , and when a ₁ is 2 or more, L 2 of 2 or more are the same or different from each other. a2, a11 and a12 can be understood with reference to the description of a1 and the structures of the formulas (1) and (10).

According to one embodiment, a1, a2, a11 and a12 in the above formula (1) may be independently 0, 1 or 1, but are not limited thereto.

Ar ₁ , Ar ₁₁ and Ar ₁₂ in the general formulas (1) and (10) independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, Ar ₁ , Ar _11, and Ar ₁₂ , independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, A phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthryl group, a phenanthrenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, and the like. Pentacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrole group, and the like. Pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, thiazolyl, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoindolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridine group, Phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzothiophenyl, Benzothiazolyl, isobenzothiazolyl, benzoxazoyl, Benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzocarbazolyl, and the like. ), Dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and the like. And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, Cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylthiophenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, , A pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, A furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group , A naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, , An isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, dibenzo carbazole group, a thiadiazole group, imidazolidin jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) from the at least one selected substituted, a phenyl group, a biphenyl group, terphenyl A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, , A triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, An isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, A benzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazole group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; ≪ / RTI >

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

As another example, Ar ₁ , Ar ₁₁ and Ar ₁₂ may be independently selected from the group consisting of the following formulas (5-1) to (5-79)

Of the above formulas (5-1) to (5-79)

Y ₃₁ and Y ₃₂ is independently of each other O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or Si (Z ₃₆ ) (Z ₃₇ );

Z ₃₁ to Z ₃₇ are, independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-non-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group , Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , it is selected from di-benzofuranyl group, a dibenzo-thio group, a benzoyl group imidazole group, a phenanthryl group trolley, possess yttria and _{-Si (Q 31) (Q 32} ) (Q 33),

Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,

e2 is 1 or 2,

e3 is selected from integers from 1 to 3,

e4 is selected from integers from 1 to 4,

e5 is selected from integers from 1 to 5,

e6 is selected from integers from 1 to 6,

e8 is selected from integers from 1 to 8,

* Is a binding site with neighboring atoms.

According to one embodiment, Ar ₁ , Ar ₁₁ and Ar ₁₂ may be independently selected from the group consisting of the following formulas (6-1) to (6-44)

In the above formulas (6-1) to (6-44), * denotes a bonding site with neighboring atoms.

B1, b11, and b12 in the general formulas (1) and (10) may be independently selected from integers of 1 to 5. b1 is if b1 is 2 or more as shown a number of 2 or more of Ar ₁ Ar ₁ is the same as or different from each other. The description of b11 and b12 can be understood with reference to the description of b1 and the structures of the formulas (1) and (10).

According to one embodiment, b1, b11 and b12 may be, independently of each other, 1 or 2, or 1, but is not limited thereto.

In the above formulas, R ₁ to R ₈ and R ₁₄ to R ₁₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, 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 aryl group, A substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 ring - C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or non-substituted 1-room Heterocyclic group condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 1) (Q 2), -B (Q 1) (Q 2), -C (= O) ( is selected from _{Q 1), -S (= O} ) 2 (Q 1) , and _{-P (= O) (Q 1} ) (Q 2),

R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, 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, a substituted Or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ Substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio groups, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ), -B (Q ₁ ) (Q ₂ ), Can be selected from -C (= O) (Q ₁ ), -S (= O) ₂ (Q ₁ ) and -P (= O) (Q ₁ ) (Q ₂ ).

For example, in the above formulas, R ₁ to R ₈ and R ₁₄ to R ₁₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a non-substituted or unsubstituted 1-hetero-condensed polycyclic aromatic group, and -Si (Q ₁₎ (Q < ₂ >) (Q < ₃ &

R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, An unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic It may be selected from the group, and _{-Si (Q 1) (Q 2} ) (Q 3).

As another example, R ₁ to R ₈ and R ₁₄ to R ₁₇ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ An alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and at least one substituted hydrazine of the tank group, a C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group , A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, A quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzoxazolyl group, An isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group , As already jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) at least one substituted phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, of the spy A phenanthryl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, A benzothiophene group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, an oxadiazolyl group, a triazolyl group, a thiazolyl group, a thiazolyl group, A dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridine group, Group and a di-imidazo pyrimidinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); ≪ / RTI >

R ₁₁ to R ₁₃ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ An alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and at least one substituted hydrazine of the tank group, a C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group , A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, A quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzoxazolyl group, An isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group , Already jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) to the at least one substituted, a fluorenyl group, of the spy-fluorenyl group, benzo fluorenyl group, di A benzofuranyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); ≪ / RTI >

Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

According to one embodiment, R ₁ to R ₈ and R ₁₄ to R ₁₇ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ An alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and the crude hydrazone group by at least one of the substituted, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group A naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group substituted with at least one of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group,

R ₁₁ to R ₁₃ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ An alkoxy group; ≪ / RTI >

According to another embodiment, R ₁ to R ₈ and R ₁₁ to R ₁₃ are hydrogen and R ₁₄ to R ₁₇ are independently of each other hydrogen or a methyl group.

In the above formulas (2A) to (2C), c11 to c13 are independently selected from integers of 0 to 4. c11 represents the number of R < _{11 &} gt ;, and when c1 is 2 or more, 2 or more R < ₁₁ > The description of c12 and c13 can be understood with reference to the description of c11 and the structures of the formulas (2A) to (2C).

According to one embodiment, c11 to c13, independently of each other, can be 0 or 1.

According to one embodiment, the condensed ring compound may be represented by one of the following formulas 1-1 to 1-42:

≪ Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

&Lt; Formula 1-5 >

<Formula 1-6>

<Formula 1-7>

&Lt; Formula (1-8)

&Lt; Formula (1-9)

&Lt; Formula 1-10 >

&Lt; Formula 1-11 &

<Formula 1-12>

&Lt; Formula 1-13 &

&Lt; Formula 1-14 &

&Lt; Formula 1-15 &

<Formula 1-16>

&Lt; Formula 1-17 &

(1-18)

(1-19)

<Formula 1-20>

<Formula 1-21>

<Formula 1-22>

<Formula 1-23>

<Formula 1-24>

<Formula 1-25>

<Formula 1-26>

<Formula 1-27>

<Formula 1-28>

<Formula 1-29>

<Formula 1-30>

<Formula 1-31>

&Lt; Formula (1-32)

<Formula 1-33>

<Formula 1-34>

<Formula 1-35>

<Formula 1-36>

<Formula 1-37>

<Formula 1-38>

<Formula 1-39>

<Formula 1-40>

<Formula 1-41>

<Formula 1-42>

A description of X ₁ , X ₂ , L ₁ , L ₂ , a ₁ , a ₂ , Ar ₁ , b ₁ , R ₁ to R ₈ , R ₁₁ to R ₁₃ and c ₁₁ to c ₁₃ Refer to what is described herein.

According to another embodiment, the condensed ring compound may be represented by one of the following formulas (1-1) to (1-42) (1):

&Lt; Formula 1-1 (1) >

&Lt; Formula 1-2 (1) >

&Lt; Formula 1-3 (1) >

&Lt; Formula 1-4 (1) >

&Lt; Formula 1-5 (1) >

&Lt; Formula 1-6 (1) >

&Lt; Formula 1-7 (1) >

&Lt; Formula 1-8 (1) >

&Lt; Formula 1-9 (1) >

&Lt; Formula 1-10 (1) >

&Lt; Formula 1-11 (1) >

&Lt; Formula 1-12 (1)

&Lt; Formula 1-13 (1) >

&Lt; Formula 1-14 (1) >

&Lt; Formula 1-15 (1) >

&Lt; Formula 1-16 (1)

&Lt; Formula 1-17 (1) >

&Lt; Formula 1-18 (1) >

&Lt; Formula 1-18 (1) >

&Lt; Formula 1-19 (1) >

&Lt; Formula 1-20 (1) >

&Lt; Formula 1-21 (1) >

<Formula 1-22 (1)>

<Formula 1-23 (1)>

&Lt; Formula 1-24 (1) >

&Lt; Formula 1-25 (1) >

<Formula 1-26 (1)>

&Lt; Formula 1-27 (1) >

&Lt; Formula 1-28 (1) >

&Lt; Formula 1-29 (1) >

&Lt; Formula 1-30 (1) >

&Lt; Formula 1-31 (1) >

&Lt; Formula 1-32 (1) >

&Lt; Formula 1-33 (1) >

&Lt; Formula 1-34 (1) >

&Lt; Formula 1-35 (1) >

<Formula 1-36 (1)>

&Lt; Formula 1-37 (1) >

&Lt; Formula 1-38 (1) >

&Lt; Formula 1-39 (1) >

&Lt; Formula 1-40 (1) >

&Lt; Formula 1-41 (1) >

&Lt; Formula 1-42 (1) >

The descriptions of X ₁ , X ₂ , L ₁ , L ₂ , a ₁ , a ₂ , Ar ₁ and b 1 in the above formulas 1-1 (1) to 1-42 (1) are as described in the present specification.

For example, X ₁ is selected from O, S and C (R ₁₄ ) (R ₁₅ )

X ₂ is selected from O and S,

L &lt; _{1 &gt;} and L &lt; ₂ &gt; are independently selected from the group consisting of the above-mentioned formulas 4-1 to 4-35,

a1 and a2 are, independently of each other, 0 or 1,

Ar ₁ is selected from the group consisting of Formulas 6-1 to 6-44,

b1 may be 1 or 2;

The fused-ring compound may be one of the following compounds:

Among the condensed ring compounds represented by Formula 1, the B ₂ ring is selected from C ₇ -C ₆₀ aromatic rings and C ₁ -C ₆₀ heteroaromatic rings, so that the size of the entire molecular structure increases and heteroatoms (for example, O Or S is easily dispersed, whereby the entire molecular structure can be stabilized. Therefore, the organic light emitting device including the condensed cyclic compound can achieve high efficiency and long life.

The condensed ring compound is suitable for use as a host of the light emitting layer because one of the groups represented by the formulas (2A) to (2C) is bonded to a specific position as shown by the following formula (1-1 '), An organic light emitting device including a condensed cyclic compound can achieve high efficiency and long life.

<Formula 1-1 '

The condensed ring compound represented by the formula (1) can be synthesized using a known organic synthesis method. The method for synthesizing the condensed ring compound can be recognized by those skilled in the art with reference to the following examples.

Thus, the first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one condensed ring compound represented by the formula (1).

In the present specification, the phrase "(the organic layer) contains one or more condensed ring compounds" means that one or more condensed ring compounds belonging to the general formula (1) Or more of the condensed ring compound. "

For example, the organic layer may contain only the compound 1 as the condensed ring compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the condensed ring compound. In this case, the compound 1 and the compound 2 are present in the same layer (for example, the compound 1 and the compound 2 may all be present in the light emitting layer) or exist in different layers (for example, And the compound 2 may be present in the light emitting layer).

Wherein the organic layer comprises i) a hole transporting region interposed between the first electrode (anode) and the light emitting layer and including at least one of a hole injecting layer, a hole transporting layer, a buffer layer and an electron blocking layer, ii) And an electron transport region interposed between the first electrode and the second electrode (cathode) and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. At least one of the hole transporting region and the light emitting layer may contain at least one of the condensed cyclic compound represented by Formula 1. For example, the light emitting layer of the organic light emitting device may include at least one of the condensed ring compounds represented by Formula 1. The condensed ring compound represented by Chemical Formula 1 included in the light emitting layer may serve as a host, and the light emitting layer may further include a dopant. The dopant may be a phosphorescent dopant or a fluorescent dopant. According to one embodiment, the dopant may be a fluorescent dopant.

In the present specification, the term "organic layer" refers to all single layers and / or plural layers interposed between the first electrode and the second electrode of the organic light emitting device. The material contained in the layer of the "organic layer" is not limited to an organic material.

[Description of FIG. 1]

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure and a manufacturing method of the organic light emitting diode 10 according to an embodiment of the present invention will be described with reference to FIG.

[First electrode 110]

A substrate may be further disposed below the first electrode 110 or over the second electrode 190 of FIG. As the substrate, a glass substrate or a plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 110 may be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. When the first electrode 110 is an anode, the first electrode material may be selected from a material having a high work function so that hole injection is facilitated.

The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 110 which is a transmissive electrode, the first electrode material may be at least one selected from the group consisting of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) But the present invention is not limited thereto. (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), or the like may be used for forming the first electrode 110 which is a transflective electrode or a reflective electrode. ), Calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof.

The first electrode 110 may have a single-layer structure or a multi-layer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

[Organic layer (150)]

An organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer.

The organic layer 150 may include a hole transport region interposed between the first electrode 110 and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode 190. [ region. &lt; / RTI &gt;

[Hole transporting region in the organic layer 150]

The hole transporting region may be a single layer structure consisting of i) a single layer of a single material, ii) a single layer of a single layer of a plurality of different materials, or iii) a multi-layer Structure.

The hole transporting region may include at least one layer selected from a hole injecting layer (HIL), a hole transporting layer (HTL), a light emitting auxiliary layer, and an electron blocking layer (EBL).

For example, the hole transporting region may have a single layer structure of a single layer made of a plurality of different materials, or may have a hole injection layer / hole transporting layer, a hole injecting layer / A multilayer structure of a light emitting auxiliary layer, a hole injecting layer, a light emitting auxiliary layer, a hole transporting layer, a light emitting auxiliary layer, a hole injecting layer, a hole transporting layer and an electron blocking layer may be used.

The hole-transporting region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, beta-NPB, TPD, Spiro-TPD, Spiro- NPB, methylated -NPB, TAPC, HMTPD, TCTA (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate), Pani / CSA (polyaniline / camphor sulfonicacid) Poly (4-styrenesulfonate) / poly (4-styrenesulfonate), PANI / PSS (polyaniline) You can include more:

&Lt; Formula 201 >

&Lt; EMI ID =

Of the above formulas (201) and (202)

L ₂₀₁ to L ₂₀₄ are independently of each other, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Aromatic dicarboxylic polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group,

L is _205, * -O- * ', * -S- *', * -N (Q 201) - * ', substituted or unsubstituted C ₁ -C ₂₀ an alkyl group, a substituted or unsubstituted C ₂ - C ₂₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent Aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group,

xa1 to xa4 are independently selected from integers of 0 to 3,

xa &lt; 5 &gt; is selected from integers from 1 to 10,

R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 Substituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic group Can be selected from among polycyclic groups.

For example, R ₂₀₁ and R ₂₀₂ in formula (202) may optionally be connected to each other through a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R ₂₀₃ and R ₂₀₄ , A single bond, a dimethyl-methylene group or a diphenyl-methylene group.

According to one embodiment, of the above formulas (201) and (202)

L ₂₀₁ to L ₂₀₅ independently from each other,

A phenylene group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptarenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spirobifluorenylene group, A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a phenanthrenylene group, A thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, an isoindolylene group, an isoindolylene group, a naphthalene group, , Benzopyranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilyloylene group and pyridinylene group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, A cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C ₁ -C ₁₀ alkyl group, a phenyl group substituted with -F, a pentyl An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group , A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, Rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzo (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) (Q ₃₃ ) (Q ₃₃ ) (Q ₃₃ ) (wherein Q represents a hydrogen atom or a methyl group), a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ), and _{-N (Q 31) (Q 32} ) inde at least one substituted phenyl group, pental alkylenyl group, selected from a carbonyl group, a naphthyl group, an azulenyl group, a heptal alkylenyl group, indazol hexenyl group, a naphthyl acetate A phenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a thienylene group, a thienylene group, a thienylene group, A phenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranyl Group, benzo thiophenyl group, a dibenzo-furanyl group, a dibenzo thiophenyl group, a benzo carbazolyl group, a dibenzo-carbazolyl group, a dibenzo room rolil group and a pyridinyl group;

&Lt; / RTI &gt;

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

According to another embodiment, xa1 to xa4 can be, independently of one another, 0, 1 or 2.

According to another embodiment, xa5 can be 1, 2, 3 or 4.

According to another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ independently represent a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pivaloyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, A benzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridinyl group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, A cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C ₁ -C ₁₀ alkyl group, a phenyl group substituted with -F, a pentyl An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group , A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, Rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzo (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) (Q ₃₃ ) (Q ₃₃ ) (Q ₃₃ ) (wherein Q represents a hydrogen atom or a methyl group), a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ), and _{-N (Q 31) (Q 32} ) from the at least one selected substituted, a phenyl group, a biphenyl group, a terphenyl group, a pen Frontale group, an indenyl group, a naphthyl group, an azulenyl group, a heptyl group Frontale, indazol hexenyl group, an acetoxy A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a pyrenyl group, a pyrenyl group, a thienyl group, A naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, , Indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group A benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilylyl group, and a pyridinyl group;

, &Lt; / RTI &gt;

The descriptions of Q ₃₁ to Q ₃₃ refer to those described in this specification.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₃ in the formula (201)

A fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, A cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C ₁ -C ₁₀ alkyl group, a phenyl group substituted with -F, a naphthyl group A spiro-bifluorenyl group, a carbazolyl group, a diaryl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, A benzofuranyl group and a dibenzothiophenyl group;

, But is not limited thereto.

According to another embodiment, i) R ₂₀₁ and R ₂₀₂ in formula (202) above may be connected to each other through a single bond, and / or ii) R ₂₀₃ and R ₂₀₄ may be connected to each other through a single bond.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₄ in the formula (202)

Carbazolyl group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, A cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C ₁ -C ₁₀ alkyl group, a phenyl group substituted with -F, a naphthyl group A carbazolyl group substituted with at least one member selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

, But is not limited thereto.

The compound represented by Formula 201 may be represented by the following Formula 201A:

&Lt; Formula 201A >

For example, the compound represented by Formula 201 may be represented by the following Formula 201A (1), but is not limited thereto:

<Formula 201A (1)>

As another example, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

Meanwhile, the compound represented by Formula 202 may be represented by Formula 202A:

&Lt; Formula 202A >

According to another embodiment, the compound represented by Formula 202 may be represented by the following Formula 202A-1:

<Chemical Formula 202A-1>

Of the above formulas 201A, 201A (1), 201A-1, 202A and 202A-1,

The descriptions of L ₂₀₁ to L ₂₀₃ , xa 1 to xa 3, xa 5, and R ₂₀₂ to R ₂₀₄ are given in this specification,

For a description of R ₂₁₁ and R ₂₁₂ , reference is made to the description of R ₂₀₃ in this specification,

R ₂₁₃ to R ₂₁₇ are independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ substituted with -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, C ₁ -C ₁₀ alkyl group An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzyl group, a benzyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenenyl group, a perylenyl group , Pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, A dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridinyl group may be selected from the group consisting of a benzoyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzothiophenyl group, .

The hole transporting region may include, but is not limited to, at least one compound selected from the following compounds HT1 to HT39:

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. If the hole transporting region includes at least one of a hole injection layer and a hole transporting layer, the thickness of the hole injection layer is about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å To about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

The light-emitting layer is a layer that functions to increase the light emission efficiency by compensating an optical resonance distance according to the wavelength of light emitted from the light emitting layer. The electron blocking layer is a layer that prevents the injection of electrons from the electron transport region to be. The light-emitting auxiliary layer and the electron blocking layer may include the above-mentioned materials.

[p-dopant]

In addition to the materials described above, the hole transporting region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-producing material may be, for example, a p-dopant.

According to one embodiment, the LUMO of the p-dopant may be -3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.

For example, the p-

Quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane);

Metal oxides such as tungsten oxide and molybdenum oxide;

HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile); And

A compound represented by the formula (221);

, But is not limited to:

<HAT-CN> <F4-TCNQ>

<Formula 221>

Of the above formula (221)

R ₂₂₁ to R ₂₂₃ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent Aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, at least one of R ₂₂₁ to R ₂₂₃ is selected from the group consisting of a cyano group, -F, -Cl, -Br, -I, At least one selected from the group consisting of a C ₁ -C ₂₀ alkyl group substituted with -F, a C ₁ -C ₂₀ alkyl group substituted with -Cl, a C ₁ -C ₂₀ alkyl group substituted with -Br, and a C ₁ -C ₂₀ alkyl group substituted with -I And has one substituent.

[Light emitting layer in organic layer 150]

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each sub-pixel. Alternatively, the light-emitting layer may have a structure in which two or more layers selected from a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are in contact with or spaced from each other or a layered structure in which two or more materials selected from a red light emitting material, a green light emitting material, It is possible to emit white light.

The light emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

The content of the dopant in the light emitting layer may be selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be 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-described range, it is possible to exhibit excellent light-emitting characteristics without substantial increase in driving voltage.

 [Host in the light emitting layer]

The host may comprise a condensed ring compound as described above.

According to one embodiment, the host may be composed of the first compound as described above.

 (Phosphorescent dopant contained in the light emitting layer in the organic layer 150)

The phosphorescent dopant may include an organometallic complex represented by the following formula (401): &lt; EMI ID =

&Lt; Formula 401 >

_{M (L 401) xc1 (L} 402) xc2

&Lt; EMI ID =

Of the above formulas (401) and (402)

M is at least one selected from the group consisting of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, ) And thulium (Tm)

L ₄₀₁ is selected from the ligands represented by the above formula (402), xc1 is 1, 2 or 3, and when xc1 is 2 or more, L _{401 's} equal to or different from each other are the same or different,

L ₄₀₂ is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, L ₄₀₂ of 2 or more are the same or different from each other,

X ₄₀₁ to X ₄₀₄ independently of one another are nitrogen or carbon,

X ₄₀₁ and X ₄₀₃ are connected through a single bond or a double bond, X ₄₀₂ and X ₄₀₄ are connected through a single bond or a double bond,

A ₄₀₁ and A ₄₀₂ independently of one another are a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

X ₄₀₅ is a single bond, * -O- * ', * -S- *', * -C (= O) - * ', * -N (Q 411) - *', * -C (Q 411) ( _{Q 412) - * ', *} -C (Q 411) = C (Q 412) - *', * -C (Q 411) = * ' or _{* = C (Q 411) =} *' , and the Q ₄₁₁ And Q ₄₁₂ are hydrogen, deuterium, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

X ₄₀₆ is a single bond, O or S,

R ₄₀₁ and R ₄₀₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, A substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ ring - C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or unsubstituted monovalent non-ring aromatic condensed polycyclic heterocyclic group _{-Si (Q 401) (Q 402} ) (Q 403), -N (Q 401) (Q 402), -B (Q 401) (Q 402), - C (= O) (Q ₄₀₁ ), -S (= O) ₂ (Q ₄₀₁ ) _{P (= O) (Q 401} ) (Q 402) is selected from the Q ₄₀₁ to Q ₄₀₃ are independently of each other, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₂₀ aryl group And a C ₁ -C ₂₀ heteroaryl group,

xc11 and xc12 are each independently selected from an integer of 0 to 10,

In the above formula (402), * and * are binding sites for M in Formula (401).

According to one embodiment, A ₄₀₁ and A ₄₀₂ in the formula (402) independently of one another are a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, furan group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, quinoline group, iso A benzoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzoimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, A triazole group, a triazole group, a dibenzofuran group, and a dibenzothiophene group.

According to another embodiment, i) X ₄₀₁ of formula 402 is nitrogen and X ₄₀₂ is carbon, or ii) both X ₄₀₁ and X ₄₀₂ may be nitrogen.

According to another embodiment, in formula (402), R ₄₀₁ and R ₄₀₂ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ An alkoxy group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazino, phenyl, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of a methanyl group, a norbornanyl group and a norbornenyl group;

A cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, A thiazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, A cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, A cyclopentyl group, a cycloheptyl group, a cyclohexyl group, a cycloheptyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, A naphthyl group, a pyridazinyl group, a triazinyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, A dibenzofuranyl group, and a dibenzothiophenyl group; And

_{-Si (Q 401) (Q 402} ) (Q 403), -N (Q 401) (Q 402), -B (Q 401) (Q 402), -C (= O) (Q 401), -S (= O) ₂ (Q ₄₀₁ ) and -P (= O) (Q ₄₀₁ ) (Q ₄₀₂ );

&Lt; / RTI &gt;

Q ₄₀₁ to Q ₄₀₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group and a naphthyl group, but are not limited thereto.

According to yet another embodiment, if the above formula 401 xc1 is 2 or more of, two of the two or more L ₄₀₁ of A ₄₀₁ are either selectively connected to each other through a by (optionally), connected group X _407, 2 of A ₄₀₂ is optionally , And X ₄₀₈ (see the following compounds PD1 to PD4 and PD7). X ₄₀₇ and X ₄₀₈ are, independently of each other, a single bond, * -O- *, * -S- *, -C (= O) -, -N (Q ₄₁₃ ) _{* -C (Q 413) (Q} 414) - * ' or _{* -C (Q 413) = C} (Q 414) - *' ( wherein, Q ₄₁₃ and Q ₄₁₄ are independently, hydrogen, deuterium, C ₁ to each other -C ₂₀ alkyl group, may be a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group), and the like.

In the above formula (401), L ₄₀₂ may be any monovalent, divalent or trivalent organic ligand. For example, the L ₄₀₂ can be a halogen, a diketone (e.g., acetylacetonate), a carboxylic acid (e.g., picolinate), -C (= O), isonitrile, -CN, (For example, phosphine, phosphite), but are not limited thereto.

Alternatively, the phosphorescent dopant can be selected, for example, from the following compounds PD1 to PD25, but is not limited thereto:

 [Fluorescent dopant in the light emitting layer]

The fluorescent dopant may include an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by the following formula (501): &lt; EMI ID =

<Formula 501>

In the above formula (501)

Ar ₅₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

L ₅₀₁ to L ₅₀₃ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Aromatic dicarboxylic polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group,

xd1 to xd3 are independently selected from integers of 0 to 3,

R ₅₀₁ and R ₅₀₂ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 unsubstituted from an aromatic heterocyclic fused polycyclic group--C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non- Selected,

And Xd4 may be selected from an integer of 1 to 6.

According to one embodiment, Ar ₅₀₁ in the formula (501)

A phenanthrene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a phenanthrene group, a naphthalene group, a hepthalene group, a fluorene group, a spirobifluorene group, , Pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group and indenophenanthrene group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , Naphthalene group, heptalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group which is substituted with at least one selected from phenyl group, biphenyl group, terphenyl group and naphthyl group Group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indeno anthracene group, Toren Group;

&Lt; / RTI &gt;

According to another embodiment, L ₅₀₁ to L ₅₀₃ in the formula (501) are, independently of each other,

And examples thereof include a phenylene group, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, A phenylene group, a phenanthrene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzoyl group, A benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilyloylene group, a pyridinylene group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a benzopyranyl group, a benzopyranyl group, , A dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridinyl group, a phenylene group, a naphthylene group, a fluorenylene group, a spy A fluorobenylene group, a fluorobenylene group, a fluorobenylene group, a fluorobenylene group, A phenanthrene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a klychenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, A thiophene group, a naphthylene group,

&Lt; / RTI &gt;

According to another embodiment, R ₅₀₁ and R ₅₀₂ in the formula (501) are, independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A perfluorenyl group, a perylenyl group, a pentenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, Dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzoylsilyl group and pyridinyl group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a benzopyranyl group, a benzopyranyl group, , it dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a dibenzo silole group, a pyridinyl group, and -Si (Q ₃₁₎ at least one substitution selected from (Q ₃₂₎ (Q ₃₃₎ Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorene, A perylene group, a perylene group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophene group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A benzothiophenyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a dibenzothiopyranyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A pyridinyl group;

&Lt; / RTI &gt;

Q ₃₁ to Q ₃₃ may be selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

According to another embodiment, xd4 in formula (501) may be 2, but is not limited thereto.

For example, the fluorescent dopant can be selected from the following compounds FD1 to FD22:

Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto.

 [Electron transporting region of the organic layer 150]

The electron transporting region may be a single-layer structure consisting of i) a single layer of a single material, ii) a single layer of a single layer of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers of a plurality of different materials Lt; / RTI &gt;

The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may include an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / An electron injection layer, and the like, but the present invention is not limited thereto.

The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer or the electron transport layer) of the electron transport region may include a metal-free compound containing at least one π electron- .

Means a C ₁ -C ₆₀ heterocyclic group having at least one * -N = * moiety as a ring-forming moiety.

For example, the "pi electron deficient nitrogen ring" is a 5- to 7-membered heteromonocyclic group having at least one * -N = * moiety, or ii) at least one * Or a heterocyclic group in which at least two of the 5-membered to 7-membered heteromonocyclic groups having the N = * 'moiety are condensed with each other, or iii) a 5-membered heterocyclic group having at least one * -N = To 7-membered heteromonocyclic group and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

Specific examples of the? Electron-deficient nitrogen ring include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, , Quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cyanol, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, isobenzothiazole, benzo But are not limited to, oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, azacavazole and the like.

For example, the electron transporting region may include a compound represented by the following formula (601).

<Formula 601>

[Ar ₆₀₁ ] _{xe 11} - [(L ₆₀₁ ) _{xe 1} -R ₆₀₁ ] _{xe 21}

In the above formula (601)

Ar ₆₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xe11 is 1, 2 or 3,

L ₆₀₁ represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group,

xe1 is selected from an integer of 0 to 5,

R ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted Import C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 T , A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₆₀₁ ) _{(Q 602) (Q 603)} , - is selected from _{-C (= O) (Q 601} ), -S (= O) 2 (Q 601) and _{-P (= O) (Q 601} ) (Q 602) ,

Q ₆₀₁ to Q ₆₀₃ independently represent a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,

and xe21 is selected from an integer of 1 to 5.

According to one embodiment, at least one of the xe11 Ar ₆₀₁ and xe21 R ₆₀₁ may include a π electron-deficient nitrogen-containing ring as described above.

According to one embodiment, the ring Ar ₆₀₁ of formula (601)

Benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, A pyrene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indeno anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, , An isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, A phenanthroline group, a phenanthroline group, a benzoimidazole group, an isobenzothiazole group, a phenanthridine group, a phenanthridine group, a quinoxaline group, a quinazoline group, A thiazole group, a thiadiazole group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and azacarbazine group, A sol group; And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , a phenyl group, a biphenyl group, a terphenyl group, a naphthyl _{group, -Si (Q 31) (Q} 32) (Q 33), -S (= O) 2 (Q 31) and _{-P (= O) (Q 31} ) ( Q ₃₂ ), benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, A perylene group, a perylene group, a fluorene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, An imidazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, A pyrazine group, a pyrazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, Group, a phenanthroline group, a phenazine group, a benzoimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, Thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacavazole group;

, &Lt; / RTI &gt;

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

In the above formula (601), when xe 11 is 2 or more, two or more Ar ₆₀₁ may be connected to each other through a single bond.

According to another embodiment, Ar ₆₀₁ in Formula 601 may be an anthracene group.

According to another embodiment, the compound represented by Formula 601 may be represented by the following Formula 601-1:

<Formula 601-1>

In the above general formula (601-1)

₆₁₄ X is N or C (R _614), X ₆₁₅ is N or C (R ₆₁₅₎ and, ₆₁₆ X is N or C (R _616), at least one of X ₆₁₄ to ₆₁₆ X is N,

L ₆₁₁ to L ₆₁₃ independently of each other refer to the description of L ₆₀₁ above,

xe611 to xe613 independently of one another refer to the description of xe1 above,

R ₆₁₁ to R ₆₁₃ independently of one another refer to the description of R ₆₀₁ above,

R ₆₁₄ to R ₆₁₆ are independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ may be selected from an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to one embodiment, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ in the general formulas (601) and (601-1)

And examples thereof include a phenylene group, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, A phenylene group, a phenanthrene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzoyl group, And examples thereof include a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzocylolylene group, a pyridinylene group, , A thiazolyl group, an isothiazolyl group, an isothiazolylene group, an isoxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazoloylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, A benzoyl group, an isoquinolinylene group, A phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrenyl group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, Imidazolidinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; an imidazolyl group, an imidazolyl group, an isobenzothiazolyl group, a benzooxazolylene group, an isobenzoxazoloylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, And

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a benzopyranyl group, a benzopyranyl group, , Dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzoylsilyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diazo, isoxazolyl, diazo, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridyl A thienyl group, a thienyl group, a thiazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, , A phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyrimidinyl group Naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylenylene group, phenanthrenylene group, and phenanthrenylene group which are substituted with at least one member selected from the group consisting of a phenanthrene group, , Anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, klychenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentachenylene group, thiophenylene group, Rengi, Indole A dibenzothiophenylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, A thiadiazolylene group, an oxadiazolene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, an imidazolyl group, , A thiazylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a shenolinylene group, A thiophene group, a thiophene group, a thiophene group, a thiophene group, a thiophene group, a thiophene group, a thiophene group, a thiophene group, Ridinenylene, Imida Pyrimidinyl group and a carbazolyl group aza;

, But is not limited thereto.

According to another embodiment, xe1 and xe611 to xe613 in the general formulas (601) and (601-1) may independently be 0, 1 or 2.

According to another embodiment, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ in the general formulas (601) and (601-1) are, independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A perfluorenyl group, a perylenyl group, a pentenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, A dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzoylsilyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group , Isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group , A naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthridinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, , An imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group;

C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, , A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, A thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a benzopyranyl group, a benzopyranyl group, , Dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzoylsilyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diazo, isoxazolyl, diazo, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridyl A thienyl group, a thienyl group, a thiazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, , A phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyrimidinyl group A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a dibenzofuranyl group, A thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, a thiophene group, an indolyl group, an imidazolyl group, an imidazolyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klycenyl group, a perylenyl group, Isoindolyl group, A benzothiophenyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzoylsilyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, A phenanthridinyl group, a phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, an isobenzothiazole group, an isothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; And

-S (= O) ₂ (Q ₆₀₁ ) and -P (= O) (Q ₆₀₁ ) (Q ₆₀₂ );

&Lt; / RTI &gt;

The descriptions of Q ₆₀₁ and Q ₆₀₂ refer to what is described in this specification.

The electron transporting region may include, but is not limited to, at least one compound selected from the following compounds ET1 to ET36:

Alternatively, the electron transporting region is BCP (2,9-Dimethyl-4,7- diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq 3, Balq, TAZ ( It may include at least one compound selected from 3- (Biphenyl-4-yl) -5- (4- tert -butylphenyl) -4-phenyl-4 H -1,2,4-triazole) and NTAZ.

The thickness of the buffer layer, the hole blocking layer or the electron control layer may be independently from about 20 Å to about 1000 Å, for example, from about 30 Å to about 300 Å. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer is in the range as described above, excellent hole blocking characteristics or electron control characteristics can be obtained without substantially increasing the driving voltage.

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

The electron transporting region (for example, the electron transporting layer in the electron transporting region) may further include a metal-containing material in addition to the above-described materials.

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex may be selected from Li ion, Na ion, K ion, Rb ion and Cs ion, and the metal ion of the alkaline earth metal complex is selected from the group consisting of Be ion, Mg ion, Ca ion, Ions. The ligand coordinated to the metal ion of the alkali metal complex and the alkaline earth metal complex may be independently selected from the group consisting of hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl There may be mentioned oxazole, hydroxyphenyl thiazole, hydroxydiphenyl oxadiazole, hydroxydiphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzoimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline And cyclopentadiene, but is not limited thereto.

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

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

The electron injection layer may be a single layer structure consisting of i) a single layer made of a single material, ii) a single layer made of a plurality of different materials, or iii) a multi-layered structure having a plurality of layers made of a plurality of different materials Lt; / RTI &gt;

The electron injecting layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may be selected from Li, Na, K, Rb and Cs. According to one embodiment, the alkali metal may be Li, Na or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, Gd and Tb.

The alkali metal compound, the alkaline earth metal compound and the rare earth metal compound may be selected from an oxide and a halide (for example, fluoride, chloride, bromide, iodide, etc.) of the alkali metal, the alkaline earth metal and the rare earth metal have.

The alkali metal compound may be selected from among alkali metal oxides such as Li ₂ O, Cs ₂ O and K ₂ O and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI and KI. According to one embodiment, the alkali metal compound may be selected from LiF, Li ₂ O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.

The alkaline earth metal compound may be selected from among alkaline earth metal compounds such as BaO, SrO, CaO, Ba _x Sr _1-x O (0 <x <1), Ba _x Ca _1-x O have. According to one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.

The rare earth metal compound may be selected from YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , and TbF ₃ . According to one embodiment, the rare earth metal compound are _{YbF 3, ScF 3, TbF 3} , YbI 3, ScI 3, TbI 3 may be selected from, but is not limited to such.

The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex contain ions of an alkali metal, an alkaline earth metal and a rare earth metal as described above, and the alkali metal complex, the alkaline earth metal complex and the rare earth metal complex coordinated to the metal ion of the rare earth metal complex The ligands are, independently of each other, selected from the group consisting of hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, But are not limited to, thiazole, thiodiazole, hydroxydiphenyl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene It is not.

The electron injection layer may be composed of only the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above , And the organic material. When the electron injecting layer further contains an organic matter, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, The combination may be uniformly or non-uniformly dispersed in the matrix of the organic material.

The thickness of the electron injection layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

[Second electrode 190]

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode that is an electron injection electrode. At this time, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, Can be used.

The second electrode 190 may be formed of one selected from the group consisting of Li, Ag, Mg, Al, Al-Li, Ca, Mg- ), Magnesium-silver (Mg-Ag), ITO, and IZO. The second electrode 190 may be a transmissive electrode, a transflective electrode, or a reflective electrode.

The second electrode 190 may have a single-layer structure or a multi-layer structure having a plurality of layers.

 [Description of Figs. 2 to 4]

2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are sequentially stacked. In the organic light emitting device 20 of FIG. 3, The light emitting device 30 has a structure in which the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked, and the organic light emitting device 40 of FIG. The first capping layer 210, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked.

The description of the first electrode 110, the organic layer 150, and the second electrode 190 in FIGS. 2 to 4 will be described with reference to FIG.

Light generated in the light emitting layer of the organic layer 150 of the organic light emitting devices 20 and 40 can be extracted to the outside through the first electrode 110 and the first capping layer 210 which are transflective electrodes or transmission type electrodes, Light generated in the light emitting layer of the organic layer 150 of the organic light emitting devices 30 and 40 may be extracted to the outside through the second electrode 190 and the second capping layer 220 which are transflective electrodes or transmissive electrodes.

The first capping layer 210 and the second capping layer 220 may improve external light emission efficiency by the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may be an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer containing an organic material and an inorganic material.

At least one of the first capping layer 210 and the second capping layer 220 may include at least one of a carbocyclic compound, a heterocyclic compound, an amine compound, a porphine derivative, a phthalocyanine derivative phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes and alkaline earth metal complexes. The carbocyclic compound, the heterocyclic compound and the amine compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, . According to one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may include an amine compound independently of each other.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may include, independently of each other, a compound represented by Formula 201 or a compound represented by Formula 202 have.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may comprise, independently from each other, a compound selected from the compounds HT28 to HT33 and the following compounds CP1 to CP5 However, the present invention is not limited thereto.

The organic light emitting device has been described with reference to FIGS. 1 to 4, but the present invention is not limited thereto.

Each of the layers included in the hole transporting region, the light emitting layer, and the electron transporting region may be formed by vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, A laser induced thermal imaging (LITI) method, or the like.

When each layer included in each hole transporting region, the light emitting layer, and the electron transporting region is formed by a vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 DEG C, a deposition temperature of about 10 ^In consideration of the composition to be included in the layer to be formed and the structure of the layer to be formed within a range of a vacuum of ^-8 to about 10 ^-3 torr and a deposition rate of about 0.01 to about 100 A / sec.

When each layer included in the hole transporting region, the light emitting layer, and the electron transporting region is formed by spin coating, the coating conditions are, for example, a coating speed of about 2000 rpm to about 5000 rpm and a coating speed of about 80 May be selected in consideration of the composition to be included in the layer to be formed and the structure of the layer to be formed within a heat treatment temperature range of 占 폚 to 200 占 폚.

 [General definition of substituent]

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

In the present specification, the C ₂ -C ₆₀ alkenyl group means a hydrocarbon group having at least one carbon double bond at the middle or end 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. In the present specification, the C ₂ -C ₆₀ alkenylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, a C ₂ -C ₆₀ alkynyl group means a hydrocarbon group containing at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, . In the present specification, the C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

The C ₁ -C ₆₀ alkoxy group in the present specification means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the above C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group, ethoxy group , Isopropyloxy group, and the like.

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, a cyclo Heptyl group 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 ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom Specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the above-mentioned C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring, but does not have an aromaticity, 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 means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, Lt; RTI ID = 0.0 &gt; a &lt; / RTI &gt; Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-hyrofuranyl group, a 2,3-hydrothiophenyl group And the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group means a carbocyclic aromatic system having 6 to 60 carbon atoms Quot; refers to a divalent group having &lt; RTI ID = 0.0 &gt; Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a cryanecyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ arylene If the group contains two or more rings, the 2 or more rings may be fused to each other.

As used herein, a C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms , Wherein the C ₁ -C ₆₀ heteroarylene group is optionally substituted with one or more substituents selected from the group consisting of 2 having a heterocyclic aromatic system containing from 1 to 60 carbon atoms and at least one heteroatom selected from N, O, Si, P and S as ring- Means a group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be condensed with each other.

In the present specification, the C ₆ -C ₆₀ aryloxy group indicates -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl group), the C ₆ -C ₆₀ arylthio is -SA ₁₀₃ , And A ₁₀₃ is the above-mentioned C ₆ -C ₆₀ aryl device).

In the present specification, a monovalent non-aromatic condensed polycyclic group is a condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom, and the whole molecule is a non-aromaticity. (E. G., Having from 8 to 60 carbon atoms). Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a monovalent aromatic condensed heteropolycyclic group in which two or more rings are condensed with each other and at least one of N, O, Si, P and S Means a monovalent group (for example, having from 1 to 60 carbon atoms) having a hetero atom and having a non-aromatic group as a whole molecule. Specific examples of the monovalent non-aromatic heterocyclic polycyclic group include a carbazolyl group and the like. In the present specification, the divalent non-aromatic heterocyclic polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, the C ₅ -C ₆₀ carbocyclic group means a monocyclic or polycyclic group having 5 to 60 carbon atoms including only carbon as a ring-forming atom. The C ₅ -C ₆₀ carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₅ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, it is the C ₅ -C according to the number attached to the substituent at the ₆₀ carbocyclic group, a C ₅ -C ₆₀ carbocyclic group during the various modifications can be made, such as in 3 or 4 is the group number of a group.

As used herein, the term "C ₁ -C ₆₀ heterocyclic group" means a group having the same structure as the C ₅ -C ₆₀ carbocyclic group, and as a ring-forming atom, carbon (having 1 to 60 carbon atoms) , And at least one heteroatom selected from O, Si, P, and S.

In the present specification, the substituted C ₅ -C ₆₀ carbocyclic group, the substituted C ₁ -C ₆₀ heterocyclic group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted Aromatic dicarboxylic group, a substituted dicarboxylic hetero-condensed polycyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, A substituted C ₁ -C ₁₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted 1 Is non-aromatic condensation Group and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused polycyclic group,

Deuterium (-D), -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine group Division, C ₁ -C ₆₀ alkyl, C ₂ - A C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 11) (Q 12 _{), -B (Q 11) (} Q 12), -C (= O) (Q 11), -S (= O) 2 (Q 11) and _{-P (= O) (Q 11} ) (Q 12) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group , A C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- aromatic condensed polycyclic heterocyclic _{group, -Si (Q 21) (Q} 22) (Q 23), -N (Q 21) (Q 22), -B (Q 21) (Q 22), -C (= O) _{(Q 21), -S (=} O) 2 (Q 21) and _{-P (= O) (Q 21} ) (Q 22) from the at least one selected substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ come heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl tea, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic Condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And

_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 31) (Q 32), -B (Q 31) (Q 32), -C (= O) (Q 31), -S (= O) ₂ (Q ₃₁ ) and -P (= O) (Q ₃₁ ) (Q ₃₂ );

&Lt; / RTI &gt;

Wherein Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a cyano group, a cyano group, A C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic A condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group, and a terphenyl group.

In the present specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "Bu ^t " means a tert- "Means methoxy group.

In the present specification, "biphenyl group" means "phenyl group substituted with phenyl group &quot;. The "biphenyl group" belongs to a "substituted phenyl group" in which the substituent is a "C ₆ -C ₆₀ aryl group".

In the present specification, "terphenyl group" means "phenyl group substituted with biphenyl group". The "terphenyl group" belongs to a "substituted phenyl group" in which the substituent is a "C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group".

In the present specification, * and * denote, unless otherwise defined, a bonding site with neighboring atoms in the formula.

Hereinafter, the compound and organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples. In the following Synthesis Examples, the molar equivalent of A and the molar equivalent of B in the expression "B was used instead of A"

 [Example]

Synthetic example

Synthesis Example 1: Synthesis of Compound H1

Synthesis of intermediate A

Intermediate A was synthesized according to Scheme 1-1 below:

<Reaction Scheme 1-1>

(1) Synthesis of intermediate A-1

Under an argon atmosphere, 22.0 g of 2,3-dimethoxynaphthalen-1-yl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL Was charged into a flask, heated for 8 hours, and stirred under reflux. After cooling to room temperature, the water layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 23.9 g of Intermediate A-1 (yield: 84.8%).

(2) Synthesis of intermediate A-2

Under argon atmosphere, 23.9 g of intermediate A-1 and 5 mL of anhydrous THF were added to the flask, and 60 mL of hexane solution of 1.6 M n-butyllithium was added and the reaction solution was stirred at room temperature for 4 hours. The solution was cooled to -78 deg. C and 30 ml of a THF solution of 28.1 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution, and the mixture was stirred for 2 hours. The reaction solution was extracted with ether, the water layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was washed with hexane to obtain 18.0 g (yield: 64.9%) of intermediate A-2.

(3) Synthesis of intermediate A-3

18.0 g of Intermediate A-2, 16.6 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene and 90 mL of 2M sodium carbonate solution were placed in a flask under argon atmosphere for 8 hours And the mixture was refluxed while heating. After cooling to room temperature, the reaction solution was extracted with toluene, the water layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 20.0 g (yield: 79.8%) of Intermediate A-3.

(4) Synthesis of intermediate A-4

20.0 g of the intermediate A-3 and 250 mL of dichloromethane (dehydrated) were placed in a flask and cooled to 0 占 폚. 27.5 g of BBr ₃ was added to the flask, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 ° C, carefully inactivated in methanol, and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over MgSO ₄ , and the impurities were removed through a silica gel short column. The solution was concentrated and the obtained sample was vacuum dried to obtain 18.6 g (yield: 99.6%) of intermediate A-4.

(5) Synthesis of intermediate A

18.6 g of Intermediate A-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200 ° C for 2 hours. After the completion of the reaction, the solution was cooled to room temperature, 2 L of Toluene was added to the solution, the solution was transferred to a separatory funnel and washed with water. This solution was dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The solution was concentrated and recrystallized in a mixed solvent of toluene / methanol to obtain 11.6 g of intermediate A (yield: 68.5%).

Synthesis of Compound H1

Compound H1 was synthesized according to Scheme 1-2 below:

<Reaction formula 1-2>

Under an argon atmosphere, 4.3 g of Intermediate A, 3.8 g of (10- (naphthalen-2-yl) -anthracen-9-yl) boronic acid, 0.232 g of Tetrakis (triphenylphosphine) palladium solution (20 mL) was added thereto, followed by reflux stirring for 8 hours. After cooling to room temperature, the precipitated solid was separated by filtration. The resulting solid was washed with a mixture of water and methanol, and then recrystallized with toluene to obtain 4.4 g (yield: 66.2%) of Compound H1. The resulting compound was identified via MS / FAB.

Calculation: 610.71 Measured value: 610.19

Synthesis Example 2: Synthesis of Compound H2

Compound H2 was synthesized according to Scheme 2 below:

<Reaction Scheme 2>

(1) Synthesis of intermediate H2-1

38.7 g of Intermediate A and 500 mL of tetrahydrofuran (dehydrated) were charged into a flask and cooled to -78 deg. To this was added 66 mL of n-BuLi (1.6 M in hexane) and the mixture was stirred for 2 hours while being heated to 0 ° C. Subsequently, the mixture was cooled to -78 deg. C again, and 327.5 g of B (OMe) ₃ was added thereto. The mixture was stirred at -78 DEG C for 10 minutes and then at room temperature for 5 hours. After completion of the reaction, 1N HCl aq. And the mixture was stirred at room temperature for 1 hour. It was then transferred to a separatory funnel and extracted with ethyl acetate. The solution was dried over MgSO ₄ , concentrated and washed with n-hexane to give 22.8 g of intermediate H2-1 (yield: 65.3%).

(2) Synthesis of intermediate H2-2

Under argon atmosphere, 22.8 g of intermediate H2-1, 8.4 g of 1-bromo-4-iodobenzene, 1.52 g of Tetrakis (triphenylphosphine) palladium (0), 200 mL of toluene and 100 mL of 2M sodium carbonate solution were added to the flask and heated for 8 hours And the mixture was refluxed and stirred. After cooling to room temperature, the reaction solution was extracted with toluene. After removing the water layer and the organic layer was dried with MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 23.7 g (yield: 71.7%) of intermediate H2-2.

(3) Synthesis of Compound H2

20.5 g (yield: 64.3%) of compound H2 was obtained using the same method as the synthesis of the compound H1 except that the intermediate H2-2 was used instead of the intermediate A. The resulting compound was identified via MS / FAB.

Calculated: 686.81 Readable: 686.22

Synthesis Example 3: Synthesis of Compound H3

Synthesis of intermediate B

Intermediate B was synthesized according to Scheme 3-1 below:

<Reaction Scheme 3-1>

(1) Synthesis of intermediate B-1

Under an argon atmosphere, 25.0 g of (2,3-bis (methylthio) naphthalen-1-yl) boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2- sodium carbonate solution (150 mL) was added to the flask and refluxed with heating for 8 hours. After cooling to room temperature, the water layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to obtain 24.5 g of Intermediate B-1 (yield: 82.1%).

(2) Synthesis of intermediate B-2

Under argon atmosphere, 24.5 g of intermediate B-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The solution was cooled to -78 deg. C and 30 ml of a THF solution of 28.1 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution, and the mixture was stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over Mg ₂ So ₄ and concentrated. The residue was washed with hexane to obtain 17.7 g (yield: 63.4%) of intermediate B-2.

(3) Synthesis of intermediate B-3

17.7 g of 4- (2-fluorophenyl) -2,3-bis (methylthio) naphthalen-1-yl) boronic acid, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene, 90 mL of 2M sodium carbonate solution Was added to the flask and refluxed with heating for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 18.3 g (yield: 76.2%) of Intermediate B-3.

(4) Synthesis of intermediate B-4

18.3 g of Intermediate B-3 and 250 mL of dichloromethane (dehydrated) were placed in a flask and cooled to 0 占 폚. BBr _{3 (} 27.5 g) was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 ° C, carefully inactivated in methanol, and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The solution was concentrated and the obtained sample was vacuum dried to obtain 17.2 g of Intermediate B-4 (yield: 99.5%) .

(5) Synthesis of intermediate B

17.2 g of Intermediate B-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.2 g of K2CO3 were added to the flask and stirred at 200 DEG C for 2 hours. After the reaction was completed, the solution was cooled to room temperature, and 2 L of toluene was transferred to an additional separating funnel and washed with water. This solution was dried over MgSO4, and the impurity was removed through a silica gel short column. The solution was concentrated and recrystallized in a toluene / methanol mixed solvent to obtain 10.1 g of Intermediate B (yield: 64.3%).

Synthesis of Compound H3

Compound H3 was synthesized according to the following Reaction Scheme 3-2:

<Reaction Scheme 3-2>

(1) Synthesis of intermediate H3-1

10.1 g of Intermediate B and 500 mL of tetrahydrofuran (dehydrated) were charged into a flask and cooled to -78 deg. To this was added 66 mL of n-BuLi (1.6 M in hexane) and the mixture was stirred for 2 hours while being heated to 0 ° C. Subsequently, the mixture was cooled to -78 캜 again, and 327.5 g of B (OMe) ₃ was added thereto. The mixture was stirred at -78 캜 for 10 minutes and then at room temperature for 5 hours. After completion of the reaction, 1N HCl aq. And the mixture was stirred at room temperature for 1 hour. It was then transferred to a separatory funnel and extracted with ethyl acetate. The solution was dried over MgSO ₄ , concentrated, and washed with n-hexane to obtain 5.9 g (yield: 64.1%) of Intermediate H3-1.

(2) Synthesis of intermediate H3-2

The flask was charged with 5.9 g of intermediate H3-1, 4.2 g of 1-bromo-4-iodobenzene, 0.8 g of Tetrakis (triphenylphosphine) palladium (0), 200 mL of toluene and 100 mL of 2M sodium carbonate solution under heating in an argon atmosphere And the mixture was refluxed and stirred. After cooling to room temperature, the reaction solution was extracted with toluene. After removing the water layer and the organic layer was dried with MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 6.0 g (yield: 71.6%) of Intermediate H3-2.

(3) Synthesis of Compound H3

5.1 g (Yield: 63.8%) of Compound H3 was obtained in the same manner as in the synthesis of Compound H1, except that Intermediate H3-2 was used in place of Intermediate A. The resulting compound was identified via MS / FAB.

Calculated: 718.93 Readable: 718.18

Synthesis Example 4: Synthesis of Compound H4

Compound H4 was synthesized according to Scheme 4 below:

<Reaction Scheme 4>

(1) Synthesis of intermediate H4-2

23.5 g of Intermediate H4-2 (yield: 70.6%) was obtained using the same method as the synthesis of intermediate H2-2 except that 1-bromo-3-iodobenzene was used instead of 1-bromo- %).

 (2) Synthesis of Compound H4

Except that Intermediate H4-2 was used instead of Intermediate A and (10-phenylanthracen-9-yl) boronic acid was used instead of 10- (naphthalen-2-yl) anthracen- , 18.9 g (Yield: 64.3%) of Compound H4 was obtained in the same manner as in the synthesis of Compound H1. The resulting compound was identified via MS / FAB.

Calculation: 636.21, measured: 636.75

Synthesis Example 5: Synthesis of Compound H5

Synthesis of intermediate C

Intermediate C was synthesized according to Scheme 5-1 below:

(1) Synthesis of intermediate C-1

8.2 g of 5-iodonaphtho [2,1-b] benzofuran, 10 g of 5-bromo-2- (ethoxycarbonyl) phenyl boronic acid, 0.4 g of Tetrakis (triphenylphosphine) palladium (0), 30 ml of a 2M sodium carbonate aqueous solution, The mixture was refluxed while heating for 8 hours. The resulting mixture was cooled to room temperature and extracted with toluene. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 8.8 g (Yield: 66.2%) of Intermediate C-1.

(2) Synthesis of intermediate C-2

To a solution of 8.8 g of Intermediate C-1 in 90 mL of tetrahydrofuran under argon atmosphere was added 30 mL of 1M methylmagnesium bromide tetrahydrofuran solution under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction solution under ice-cooling and extracted with toluene. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.3 g (yield: 74.1%) of Intermediate C-2.

(3) Synthesis of intermediate C

0.7 mL of sulfuric acid was added dropwise to a solution of 6.3 g of Intermediate C-2 in 70 mL of acetic acid, and the mixture was stirred at 50 占 폚 for 8 hours. The resulting mixture was cooled to room temperature, and toluene and water were added to separate the layers. The toluene layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography to obtain 2.1 g (yield: 34.6%) of Intermediate C

Synthesis of Compound H5

Compound H5 was synthesized according to Scheme 5-2 below:

<Reaction Scheme 5-2>

Except that (10-phenylanthracen-9-yl) boronic acid was used instead of 10- (naphthalen-2-yl) anthracen-9- yl) boronic acid and Intermediate C was used in place of Intermediate A, 2.2 g (Yield: 62.4%) of Compound H5 was obtained in the same manner as in the synthesis of Compound H1. The resulting compound was identified via MS / FAB.

Calc value: 712.89, measured value: 712.28

Synthesis Example 6: Synthesis of Compound H6

Synthesis of intermediate D

Intermediate B was synthesized according to Scheme 6-1 below:

<Reaction Scheme 2-1>

(1) Synthesis of intermediate D-1

Under an argon atmosphere, 32.4 g of 1,6-dimethoxynaphthalen-2-yl boronic acid, 17.6 g of 1-bromo-2-fluorobenzene, 2.34 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL Was charged into a flask, heated for 8 hours, and stirred under reflux. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 53.9 g (yield: 84.8%) of Intermediate D-1.

(2) Synthesis of intermediate D-2

Under an argon atmosphere, 53.9 g of Intermediate D-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The solution was cooled to -78 deg. C and 30 ml of a THF solution of 28.1 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. To the reaction solution was added 200 mL of 10% HCl, and the mixture was stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over Mg ₂ SO ₄ and concentrated. The residue was washed with hexane to obtain 25.1 g (yield: 64.9%) of intermediate D-2.

(3) Synthesis of intermediate D-3

Under argon atmosphere, 25.1 g of Intermediate D-2, 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene and 95 mL of 2M sodium carbonate solution were added to the flask, Was heated and refluxed with stirring. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 16.5 g of Intermediate D-3 (yield: 79.8%).

(4) Synthesis of intermediate D-4

16.5 g of the intermediate D-3 and 480 mL of N, N-dimethylformamide were placed in a flask, and a solution of 6.4 g of N, N-dimethylformamide in N-bromosuccinimide was added. The reaction solution was stirred for 5 hours at 40 &lt; 0 &gt; C. 2.2 g of N-bromosuccinimide was further added and stirring was continued at 50 DEG C for 8 hours. After cooling to room temperature, 300 mL of water was added, and then the reaction solution was extracted with toluene, the aqueous layer was removed, and washed sequentially with sodium thiosulfate. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 19.5 g of Intermediate D-4 (yield: 97.9%).

(5) Synthesis of intermediate D-5

Under argon atmosphere, 19.5 g of intermediate D-4 and 300 mL of dichloromethane (dehydration) were added to the flask, cooled to -78 ° C with stirring and 90 mL of a dichloromethane solution of 1 M boron tribromide (BBr ₃ ) was added. Stirring was continued for 3 hours while raising the temperature of the reaction solution to room temperature. The reaction solution was ice-cooled and 150 mL of water was added thereto. After removing the aqueous layer, the organic layer was dried over MgSO ₄ . The organic layer was concentrated, and the residue was purified by a silica gel short column to obtain 17.2 g (yield: 94.0%) of Intermediate D-5.

(6) Synthesis of intermediate D

17.2 g of Intermediate D-5, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.2 g of K2CO3 were added to the flask, followed by stirring at 200 DEG C for 2 hours. After the completion of the reaction, the solution was cooled to room temperature, and 2 L of toluene was added thereto. Then, the solution was transferred to a separatory funnel and washed with water. This solution was dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The solution was concentrated and recrystallized in a toluene / methanol mixed solvent to obtain 1.7 g (yield: 10.8%) of Intermediate D.

Synthesis of Compound H6

Compound H6 was synthesized according to Scheme 6-2 below:

<Reaction Scheme 6-2>

(10- (4- (dibenzo [b, d] furan-2-yl) naphthalen-1 in place of 10- (naphthalen-2-yl) anthracen- (yield: 61.7%) was obtained by using the same method as the synthesis of the compound H1 except that an anthracen-9-yl) anthracen-9-yl) boronic acid was used. The resulting compound was identified via MS / FAB.

Calculated: 718.93, found: 718.18

Synthesis Example 7: Synthesis of Compound H7

Synthesis of intermediate E

Intermediate E was synthesized according to Scheme 7-1 below:

(1) Synthesis of intermediate E-1

In a nitrogen atmosphere, 22.0 g of (3,5-dimethoxynaphthalen-2-yl) boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane, Was added to the flask and heated under reflux for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 22.4 g (yield: 83.6%) of Intermediate E-1.

(2) Synthesis of intermediate E-2

Under an argon atmosphere, 22.4 g of Intermediate E-1 and 500 mL of anhydrous THF were added to the flask, and 55 mL of hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The solution was cooled to -78 deg. C, and 30.2 mL of trimethyl borate in THF (30 mL) was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. To the reaction solution was added 200 mL of 10% HCl and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over Mg ₂ SO ₄ and concentrated. The residue was washed with hexane to obtain 16.9 g (yield: 65.2%) of intermediate E-2.

(3) Synthesis of intermediate E-3

16.8 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene and 90 mL of 2M sodium carbonate solution were placed in a flask under argon atmosphere. Lt; / RTI &gt; for 1 hour. After cooling to room temperature, the reaction solution was extracted with toluene, the water layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 18.4 g (yield: 78.3%) of Intermediate E-3.

(4) Synthesis of intermediate E-4

18.4 g of Intermediate E-3 and 250 mL of dichloromethane (dehydrated) were placed in a flask and cooled to 0 占 폚. 27.8 g of BBr3 was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 ° C, carefully inactivated in methanol, and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The obtained solution was concentrated to obtain 17.2 g (yield: 99.8%) of intermediate E-4.

(5) Synthesis of intermediate E

17.2 g of the intermediate E-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.5 g of K2CO3 were added to the flask and stirred at 200 DEG C for 2 hours. After the reaction was completed, the solution was cooled to room temperature, and 2 L of toluene was transferred to an additional separating funnel and washed with water. This solution was dried over MgSO ₄ , and the origin impurities were removed through a silica gel short column. The solution was concentrated and recrystallized in a toluene / methanol mixed solvent to obtain 10.1 g (yield: 65.1%) of Intermediate E.

Synthesis of Compound H7

Compound H7 was synthesized according to Scheme 7-2 below:

<Reaction Scheme 7-2>

(1) Synthesis of intermediate H7-1

6.0 g (Yield: 65.6%) of Intermediate H7-1 was obtained in the same manner as in the synthesis of Intermediate H2-1 except that Intermediate E was used instead of Intermediate A.

(2) Synthesis of intermediate H7-2

6.1 g (yield: 69.9%) of Intermediate H7-2 was obtained in the same manner as in the synthesis of Intermediate H7-2, except that Intermediate H7-1 was used instead of Intermediate H2-1.

(3) Synthesis of Compound H7

Except that Intermediate H7-2 was used instead of Intermediate A and (10-phenylanthracen-9-yl) boronic acid was used instead of (10- (naphthalen-2-yl) anthracen- , 4.9 g (Yield: 64.1%) of Compound H7 was obtained in the same manner as in the synthesis of Compound H1. The resulting compound was identified via MS / FAB.

Calculated: 636.75, found: 636.21

Synthesis Example 8: Synthesis of Compound H8

Synthesis of intermediate F

Intermediate F was synthesized according to Scheme 8-1 below:

<Reaction Scheme 8-1>

(1) Synthesis of intermediate F-1

Under an argon atmosphere, 25.0 g of (3,5-bis (methylthio) naphthalen-2-yl) boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2- sodium carbonate solution (150 mL) was added to the flask and refluxed with heating for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 24.8 g (83.3% yield) of intermediate F-1.

(2) Synthesis of intermediate F-2

Under argon atmosphere, 24.8 g of intermediate F-1 and 500 mL of anhydrous THF were added to the flask, and 55 mL of hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The mixture was cooled to -78 deg. C and 30.9 ml of THF in 27.9 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution, and the mixture was stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over Mg ₂ SO ₄ and concentrated. The residue was washed with hexane to give 18.2 g (yield 64.2%) of intermediate F-2.

(3) Synthesis of intermediate F-3

Under argon atmosphere, 18.2 g of intermediate F-2, 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene and 90 mL of 2M sodium carbonate solution were added to the flask, And the mixture was refluxed while heating. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 19.0 g (yield: 76.8%) of Intermediate F-3.

(4) Synthesis of intermediate F-4

19.0 g of the intermediate F-3 and 250 mL of dichloromethane (dehydrated) were put in a flask and cooled to 0 占 폚. 27.5 g of BBr3 was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 ° C, carefully inactivated in methanol, and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The obtained solution was concentrated to obtain 17.9 g of Intermediate F-4 (yield: 99.8%) .

(5) Synthesis of intermediate F

10.8 g of the intermediate F-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.2 g of K2CO3 were added to the flask and stirred at 200 DEG C for 2 hours. After the completion of the reaction, the solution was cooled to room temperature, and 2 L of toluene was added thereto. Then, the solution was transferred to a separating funnel and washed with water. This solution was dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The solution was concentrated and recrystallized in a toluene / methanol mixed solvent to obtain 10.8 g (yield: 66.1%) of Intermediate F.

Synthesis of Compound H8

Compound H8 was synthesized according to the following Reaction Scheme 8-2:

<Reaction Scheme 8-2>

(1) Synthesis of intermediate H8-1

6.4 g (Yield: 64.3%) of Intermediate H8-1 was obtained in the same manner as in the synthesis of Intermediate H2-1 except that Intermediate F was used in place of Intermediate A.

(2) Synthesis of intermediate H8-2

Except that Intermediate H7-1 was used instead of Intermediate H2-1 and 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene. 7.1 g (yield: 71.2%) of H8-2 was obtained.

(3) Synthesis of Compound H8

Except that Intermediate H8-2 was used instead of Intermediate A and (10-phenylanthracen-9-yl) boronic acid was used instead of (10- (naphthalen-2-yl) anthracen- , 5.4 g (Yield: 63.6%) of Compound H7 was obtained in the same manner as in the synthesis of Compound H1. The resulting compound was identified via MS / FAB.

Calculated: 718.93, found: 718.18

Synthesis Example 9: Synthesis of Compound H9

Synthesis of intermediate G

Intermediate G was synthesized according to Scheme 9-1 below:

<Reaction Scheme 9-1>

(1) Synthesis of intermediate G-1

Under an argon atmosphere, 25.0 g of (1,6-bis (methylthio) naphthalen-2-yl) boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2- sodium carbonate solution (150 mL) was added to the flask and refluxed with heating for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to obtain 25.4 g (yield: 85.2%) of Intermediate G-1.

(2) Synthesis of intermediate G-2

Under an argon atmosphere, 25.4 g of Intermediate G-1 and 500 mL of anhydrous THF were added to the flask, and 55 mL of hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The solution was cooled to -78 deg. C, and 30.2 mL of trimethyl borate in THF (30 mL) was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution, and the mixture was stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over Mg2SO4 and then concentrated. The residue was washed with hexane to obtain 18.8 g of intermediate G-2 (yield: 64.8%).

(3) Synthesis of intermediate G-3

18.8 g of the intermediate G-2, 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene and 90 mL of 2M sodium carbonate solution were placed in a flask under an argon atmosphere for 8 hours And the mixture was refluxed while heating. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 19.4 g (yield: 76.2%) of Intermediate G-3.

(4) Synthesis of intermediate G-4

19.4 g of the intermediate G-3 and 250 mL of dichloromethane (dehydrated) were put in a flask and cooled to 0 占 폚. 27.5 g of BBr3 was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 ° C, carefully inactivated in methanol, and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over MgSO ₄ , and the impurity was removed through a silica gel short column. The solution was concentrated to obtain 18.2 g of Intermediate G-4 (yield: 99.5%). .

(5) Synthesis of intermediate G

18.2 g of the intermediate G-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated) and 24.2 g of K2CO3 were added to the flask and stirred at 200 DEG C for 2 hours. After the completion of the reaction, the solution was cooled to room temperature, and 2 L of Toluene was added thereto. Then, the solution was transferred to a separating funnel and washed with water. This solution was dried over MgSO4, and the impurity was removed through a silica gel short column. The solution was concentrated and recrystallized in a toluene / methanol mixed solvent to obtain Intermediate G 11.2g (Yield: 67.3%).

Synthesis of Compound H9

Compound H9 was synthesized according to Scheme 8-2 below:

<Reaction Scheme 8-2>

(9- dimethyl-9H-fluoren-3-yl) anthracen-9-yl (9-yl) anthracen-9- yl) boronic acid was used instead of 10- (naphthalen- ) boronic acid was used, 12.0 g (Yield: 62.6%) of Compound H9 was obtained in the same manner as in the synthesis of Compound H1. The resulting compound was identified via MS / FAB.

Calculation: 708.94, Measured value: 708.19

Example 1

A corning 15 Ω / cm ² (1200 Å) ITO glass substrate was cut into a 50 mm × 50 mm × 0.7 mm size substrate and an anode. Ultrasonic cleaning was performed for 5 minutes using isopropyl alcohol and pure water. Ultraviolet rays were irradiated for 30 minutes Irradiated, exposed to ozone, and cleaned, and this glass substrate was placed in a vacuum deposition apparatus.

HT13 was vacuum deposited on the ITO anode to form a hole injection layer having a thickness of 500 A, and HT3 was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 450 ANGSTROM.

Compound H1 (host) and FD1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 95: 5 to form a 30 nm thick light emitting layer.

The electron transport layer was formed by depositing a compound ET1 on the light emitting layer to form a 250 Å thick electron transport layer. LiF was deposited on the electron transport layer to form a 5 Å thick electron injection layer. Al was vacuum deposited on the electron injection layer to form a 1500 Å thick To form an organic light emitting device.

Examples 2 to 9 and Comparative Examples 1 to 5

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound described in Table 2 was used in place of the compound H1 as a host in forming the light emitting layer.

Evaluation example 1

(Measurement of driving voltage)

The efficiencies of the organic light emitting devices fabricated in Examples 1 to 9 and Comparative Examples 1 to 5 were measured at a current density of 10 mA / cm ² using Kethley SMU 236, and the results are shown in Table 2.

(Measurement of half life)

The half lifetime of the organic light emitting devices fabricated in Examples 1 to 9 and Comparative Examples 1 to 5 was measured using a luminance meter PR650 at a current density of 50 mA / cm ² , and the results are shown in Table 2. The half life time is the time taken for the luminance to become 80% of the initial luminance after driving the organic light emitting element.

Host efficiency
(cd / A) Half life (T80)
(hr) Example 1 Compound H1 5.1 90 Example 2 Compound H2 5.1 110 Example 3 Compound H3 5.0 100 Example 4 Compound H4 5.1 100 Example 5 Compound H5 5.2 90 Example 6 Compound H6 5.0 100 Example 7 Compound H7 5.2 100 Example 8 Compound H8 5.0 110 Example 9 Compound H9 5.1 90 Comparative Example 1 Compound A 4.5 50 Comparative Example 2 Compound B 4.7 80 Comparative Example 3 Compound C 4.9 70 Comparative Example 4 Compound D 4.6 70 Comparative Example 5 Compound E 4.6 60

It can be seen from Table 2 that the efficiency and half life time of the organic light emitting devices of Examples 1 to 9 are superior to those of the organic light emitting devices of Comparative Examples 1 to 5 in terms of efficiency and half life.

10: Organic light emitting device
110: first electrode
150: organic layer
190: second electrode

Claims (20)

A condensed ring compound represented by the following formula (1)
&Lt; Formula 1 >

&Lt; Formula 2A >

(2B)

&Lt; Formula 2C >

&Lt; Formula 10 >

Of the above formulas (1), (2A), (2C) and (10)
A ₁ is selected from the group represented by the above formulas (2A) to (2C), n 1 is selected from integers from 1 to 3,
X ₁ is N - is selected from, O, S and _{C (R 14) (R 15} ), - [(Ar 11) b11 (L 11) a11]
The B ₂ ring, the B ₃ ring and the B ₄ ring are condensed with each other,
The B ₁ ring and the B ₄ ring are each independently selected from a C ₆ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ hetero aromatic ring,
The B ₂ ring is selected from C ₇ -C ₆₀ aromatic rings and C ₁ -C ₆₀ heteroaromatic rings,
It is selected from, O, S and _{C (R 16) (R 17} ), B 3 doedoe ring represented by the formula 10, X ₂ is _{N - - [(Ar 12)} b12 (L 12) a12]
L ₁ , L ₂ , L ₁₁ and L ₁₂ each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ hetero Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non- aromatic condensed heteropolycyclic group,
a1, a2, a11 and a12 are each independently selected from the integers of 0 to 3,
Ar ₁ , Ar ₁₁ and Ar ₁₂ are, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted aryl group, Aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups,
b1, b11 and b12 are independently selected from integers from 1 to 5,
R ₁ to R ₈ and R ₁₄ to R ₁₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, 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 alkenyl group, C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted a C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 T Substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic group Ring _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 1) (Q 2), -B (Q 1) (Q 2), -C (= O) (Q 1) , -S (= O) ₂ (Q ₁ ) and -P (= O) (Q ₁ ) (Q ₂ )
R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, 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, a substituted Or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ Substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio groups, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ), -B (Q ₁ ) (Q ₂ ), Selected from _{-C (= O) (Q 1} ), -S (= O) 2 (Q 1) , and _{-P (= O) (Q 1} ) (Q 2) and,
c11 to c13 are each independently selected from an integer of 0 to 4,
* Is the binding site with neighboring atoms,
The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ A substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ hetero A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic group selected from the substituent group of the condensed polycyclic group enemy Figure one,
Deuterium (-D), -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine group Division, C ₁ -C ₆₀ alkyl, C ₂ - A C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 11) (Q 12 _{), -B (Q 11) (} Q 12), -C (= O) (Q 11), -S (= O) 2 (Q 11) and _{-P (= O) (Q 11} ) (Q 12) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group , A C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- aromatic condensed polycyclic heterocyclic _{group, -Si (Q 21) (Q} 22) (Q 23), -N (Q 21) (Q 22), -B (Q 21) (Q 22), -C (= O) _{(Q 21), -S (=} O) 2 (Q 21) and _{-P (= O) (Q 21} ) (Q 22) from the at least one selected substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ come heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl tea, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic Condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And
_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 31) (Q 32), -B (Q 31) (Q 32), -C (= O) (Q 31), -S (= O) ₂ (Q ₃₁ ) and -P (= O) (Q ₃₁ ) (Q ₃₂ );
&Lt; / RTI >
Wherein Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, 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 ₆₀ alkoxy group, nitro group, amidino group, hydrazino group, hydrazino group, Substituted with a C ₁ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group or a C ₁ -C ₆₀ alkyl group C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group, a terphenyl group, a C ₁ -C ₆₀ heteroaryl group, a C ₁ -C ₆₀ alkyl group substituted with a C ₁ -C ₆₀ alkyl group, It is selected from a condensed polycyclic aromatic heterocyclic group-C ₆₀ heteroaryl group, a C ₆ C ₁ -C ₆₀ heteroaryl group, a monovalent non-substituted with -C ₆₀ aryl-fused polycyclic aromatic groups, and monovalent ratio. The method according to claim 1,
X ₁ is selected from O, S and C (R ₁₄ ) (R ₁₅ )
And X &lt; ₂ &gt; is O or S. The method according to claim 1,
The B ₁ ring and the B ₄ ring are benzene,
Ring B ₂ is a naphthalene, condensed ring compound. The method according to claim 1,
L ₁ , L ₂ , L ₁₁ and L ₁₂ are, independently of each other,
A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , Anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, and the like. , Perylene, perylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, obarenylguanene, Ovalenylene, pyrrolylene, isoindolinone, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, thiophenylene, thiophenylene, isoxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, isoindolylene, isoindolylene, And examples thereof include indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinyl, And examples thereof include phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, phenanthridinylene, ), Acridinylene group (acr and isocyanates such as isobenzothiazolylene, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, Benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzoyl, and the like. A dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazoylene group, an imidazopyridinylene group and an imidazopyrimidinylene group; And
C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, Cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylthiophenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, , A pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, A furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group , A naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, , An isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), a substituted or unsubstituted phenylene group, a substituted or unsubstituted phenylene group, an imidazopyrimidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, , Indenylene group, naphthylene group, azulenylene group, heptalenyl A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, And examples thereof include a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, An isoindolylene group, an indolylene group, an indazolylene group, a prolinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthaloylphenylene group, a phenanthrene group, Naphthylidene group, quinoxalinylene group, , A quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a cyclopentadienyl group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, And examples thereof include a benzoimidazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, a benzooxazolylene group, an isobenzoxazolanylene group, a triazololylene group, a tetrazolylene group, an oxadiazoleisonylene group, a triazienylene group, a dibenzofuranylene group, a dibenzothiophenylene group, , Dibenzocarbazolylene group, thiadiazoylene group, imidazopyridinylene group and imidazopyrimidinylene group; &Lt; / RTI &gt;
Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. The method according to claim 1,
Wherein L ₁ , L ₂ , L ₁₁ and L ₁₂ are independently selected from the group consisting of the following formulas (3-1) to (3-41)

Of the above-mentioned formulas (3-1) to (3-41)
Y ₁ is O, S, C (Z ₃ ) (Z ₄ ), N (Z ₅ ) or Si (Z ₆ ) (Z ₇ );
Z ₁ to Z ₇ are independently from each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-non-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group , Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , it is selected from the dibenzo furanoid group, a dibenzo-thio group, a triazinyl group, a benzoimidazol group, a phenanthryl group and a trolley _{-Si (Q 31) (Q 32} ) (Q 33),
Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,
d2 is 1 or 2,
d3 is selected from integers from 1 to 3,
d4 is selected from integers from 1 to 4,
d5 is selected from an integer of 1 to 5,
d6 is selected from integers from 1 to 6,
d8 is selected from integers from 1 to 8,
* And * are binding sites with neighboring atoms. The method according to claim 1,
Wherein L ₁ , L ₂ , L ₁₁ and L ₁₂ are each independently selected from the group consisting of the following formulas (4-1) to (4-35)

In the above formulas (4-1) to (4-35), * and * are binding sites with neighboring atoms. The method according to claim 1,
And a1, a2, a11 and a12 are, independently of each other, 0 or 1. The method according to claim 1,
Ar ₁ , Ar ₁₁ and Ar ₁₂ are, independently of each other,
A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, A phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, and the like. Pentacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrole group, and the like. Pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, thiazolyl, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoindolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridine group, Phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzothiophenyl, Benzothiazolyl, isobenzothiazolyl, benzoxazoyl, Benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzocarbazolyl, and the like. ), Dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and the like. And
C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, Cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylthiophenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, , A pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, A furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group , A naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, , An isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, dibenzo carbazole group, a thiadiazole group, imidazolidin jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) from the at least one selected substituted, a phenyl group, a biphenyl group, terphenyl A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, , A triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, An isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, A benzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazole group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; &Lt; / RTI &gt;
Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. The method according to claim 1,
Wherein Ar ₁ , Ar ₁₁ and Ar ₁₂ independently represent a condensed ring compound selected from the group consisting of the following formulas (5-1) to (5-79)

Of the above formulas (5-1) to (5-79)
Y ₃₁ and Y ₃₂ is independently of each other O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or Si (Z ₃₆ ) (Z ₃₇ );
Z ₃₁ to Z ₃₇ are, independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-non-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group , Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group (Q ₃₁ ) (Q ₃₂ ), and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), among the dibenzofuranyl group, the dibenzothiophenyl group, the benzoimidazolyl group, the phenanthrolinyl group, the triazinyl group, Selected,
Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,
e2 is 1 or 2,
e3 is selected from integers from 1 to 3,
e4 is selected from integers from 1 to 4,
e5 is selected from integers from 1 to 5,
e6 is selected from integers from 1 to 6,
e8 is selected from integers from 1 to 8,
* Is a binding site with neighboring atoms. The method according to claim 1,
Wherein Ar ₁ , Ar ₁₁ and Ar ₁₂ are, independently of each other, a condensed ring compound selected from the group consisting of the following formulas (6-1) to (6-44)

In the above formulas (6-1) to (6-44), * denotes a bonding site with neighboring atoms. The method according to claim 1,
R ₁ to R ₈ and R ₁₄ to R ₁₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, Hydra tank group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ - C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3) &Lt; / RTI &gt;
R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, An unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic , condensed ring compound is selected from the group, and _{-Si (Q 1) (Q 2} ) (Q 3). The method according to claim 1,
R ₁ to R ₈ and R ₁₄ to R ₁₇ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ An alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and at least one substituted hydrazine of the tank group, a C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group , A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, A quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzoxazolyl group, An isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group , As already jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) at least one substituted phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, of the spy A phenanthryl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, A benzothiophene group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, an oxadiazolyl group, a triazolyl group, a thiazolyl group, a thiazolyl group, A dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridine group, Group and a di-imidazo pyrimidinyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); &Lt; / RTI &gt;
R ₁₁ to R ₁₃ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ An alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and at least one substituted hydrazine of the tank group, a C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group , A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl group, A quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzoxazolyl group, An isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group , Already jopi piperidinyl group, imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) to the at least one substituted, a fluorenyl group, of the spy-fluorenyl group, benzo fluorenyl group, di A benzofuranyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); &Lt; / RTI &gt;
Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. The method according to claim 1,
R ₁ to R ₈ and R ₁₄ to R ₁₇ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ An alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, and the crude hydrazone group by at least one of the substituted, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group A naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group substituted with at least one of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group,
R ₁₁ to R ₁₃ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ An alkoxy group; &Lt; / RTI &gt; The method according to claim 1,
A condensed ring compound represented by one of the following formulas 1-1 to 1-42:
&Lt; Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

&Lt; Formula 1-5 >

<Formula 1-6>

<Formula 1-7>

&Lt; Formula (1-8)

&Lt; Formula (1-9)

&Lt; Formula 1-10 >

&Lt; Formula 1-11 &

<Formula 1-12>

&Lt; Formula 1-13 &

&Lt; Formula 1-14 &

&Lt; Formula 1-15 &

<Formula 1-16>

&Lt; Formula 1-17 &

(1-18)

(1-19)

<Formula 1-20>

<Formula 1-21>

<Formula 1-22>

<Formula 1-23>

<Formula 1-24>

<Formula 1-25>

<Formula 1-26>

<Formula 1-27>

<Formula 1-28>

<Formula 1-29>

<Formula 1-30>

<Formula 1-31>

&Lt; Formula (1-32)

<Formula 1-33>

<Formula 1-34>

<Formula 1-35>

<Formula 1-36>

<Formula 1-37>

<Formula 1-38>

<Formula 1-39>

<Formula 1-40>

<Formula 1-41>

<Formula 1-42>

A description of X ₁ , X ₂ , L ₁ , L ₂ , a ₁ , a ₂ , Ar ₁ , b ₁ , R ₁ to R ₈ , R ₁₁ to R ₁₃ and c ₁₁ to c ₁₃ Is the same as that described in claim 1. The method according to claim 1,
A condensed ring compound represented by one of the following formulas (1-1) (1) to (1-42) (1):
&Lt; Formula 1-1 (1) >

&Lt; Formula 1-2 (1) >

&Lt; Formula 1-3 (1) >

&Lt; Formula 1-4 (1) >

&Lt; Formula 1-5 (1) >

&Lt; Formula 1-6 (1) >

&Lt; Formula 1-7 (1) >

&Lt; Formula 1-8 (1) >

&Lt; Formula 1-9 (1) >

&Lt; Formula 1-10 (1) >

&Lt; Formula 1-11 (1) >

&Lt; Formula 1-12 (1)

&Lt; Formula 1-13 (1) &gt;

&Lt; Formula 1-14 (1) &gt;

&Lt; Formula 1-15 (1) &gt;

&Lt; Formula 1-16 (1)

&Lt; Formula 1-17 (1) >

&Lt; Formula 1-18 (1) >

&Lt; Formula 1-18 (1) >

&Lt; Formula 1-19 (1) >

&Lt; Formula 1-20 (1) >

&Lt; Formula 1-21 (1) >

<Formula 1-22 (1)>

<Formula 1-23 (1)>

&Lt; Formula 1-24 (1) >

&Lt; Formula 1-25 (1) >

<Formula 1-26 (1)>

&Lt; Formula 1-27 (1) >

&Lt; Formula 1-28 (1) >

&Lt; Formula 1-29 (1) >

&Lt; Formula 1-30 (1) >

&Lt; Formula 1-31 (1) >

&Lt; Formula 1-32 (1) >

&Lt; Formula 1-33 (1) >

&Lt; Formula 1-34 (1) >

&Lt; Formula 1-35 (1) >

<Formula 1-36 (1)>

&Lt; Formula 1-37 (1) >

&Lt; Formula 1-38 (1) >

&Lt; Formula 1-39 (1) >

&Lt; Formula 1-40 (1) >

&Lt; Formula 1-41 (1) >

&Lt; Formula 1-42 (1) >

The description of X ₁ , X ₂ , L ₁ , L ₂ , a ₁ , a ₂ , Ar ₁ and b 1 in the above formulas 1-1 (1) to 1-42 (1) is the same as described in the above item 1. 16. The method of claim 15,
X ₁ is selected from O, S and C (R ₁₄ ) (R ₁₅ )
X ₂ is selected from O and S,
L ₁ and L ₂ are independently selected from the group consisting of the following formulas (4-1) to (4-35)
a1 and a2 are, independently of each other, 0 or 1,
Ar ₁ is selected from the group consisting of the following formulas (6-1) to (6-44)
b1 is 1 or 2, a condensed ring compound:

In the above formulas 4-1 to 4-35 and 6-1 to 6-44, * and * 'are binding sites with neighboring atoms. A first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer comprises at least one compound selected from the group consisting of an organic light emitting element . 18. The method of claim 17,
The first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer comprises i) a hole transporting region interposed between the first electrode and the light emitting layer, the hole transporting region including at least one of a hole injection layer, a hole transporting layer, a buffer layer and an electron blocking layer, and ii) And includes an electron transporting region including at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer. 18. The method of claim 17,
Wherein the light emitting layer contains the condensed cyclic compound. 18. The method of claim 17,
Wherein the light emitting layer further comprises a fluorescent dopant.

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