KR20170138614A - Organic light emitting device comprising the same - Google Patents

Abstract

Disclosed is an organic light-emitting device containing a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2. The organic light-emitting device containing the first compound and the second compound ensures low driving voltage and high efficiency.

Description

[0001] The present invention relates to an organic light emitting device,

And an organic light emitting device.

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.

And an organic light emitting device including the first compound and the second compound represented by a predetermined formula.

According to one aspect,

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;

/ RTI >

Wherein the organic layer comprises a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2:

≪ Formula 1 >

≪ Formula 1-1 >

(2)

In the above formulas (1), (1-1) and (2)

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

The A ₁ ring, the A ₂ ring, the A ₄ ring, the A ₁₁ ring and the A ₁₂ ring are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₂ -C ₃₀ heterocyclic group,

The A ₃ ring is selected from the group represented by the formula (1-1)

X < ₁ > is O or S,

X ₂ is selected from N - [(L ₂ ) a ₂ - (R ₁ ) _{b 1} ], O and S,

X ₁₁ is selected from N and C (R ₁₁ ), X ₁₂ is selected from N and C (R ₁₂ ), at least one of X ₁₁ and X ₁₂ is N,

L ₁ through L ₅ and L ₂₁ to L ₂₃ are, each independently, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ to each other -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenylene 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 divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non- - selected from substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic groups,

a1 to a5 and a21 to a23 are each independently selected from an integer of 0 to 5,

R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano 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 ₂ -C ₆₀ alkenyl group, An unsubstituted C ₁ -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 cycloalkane Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic Condensed polycyclic heterocyclic _{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 )

b1 to b4 and b21 to b23 are independently selected from integers of 0 to 4,

c1 to c3, c22 and c23 are each independently selected from integers from 0 to 6,

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 hydrocarbon ring, at least one of the substituents of the fused 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 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, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl 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.

The organic light emitting device including the first compound and the second compound may have a low driving voltage and a high efficiency.

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

The organic light emitting device includes 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.

The first electrode may be an anode, the second electrode may be a cathode, and a description of the first electrode and the second electrode will be given later.

The organic layer includes a first compound represented by the following formula (1) and a second compound represented by the following formula (2): < EMI ID =

≪ Formula 1 >

≪ Formula 1-1 >

(2)

The A ₂ ring, the A ₃ ring and the A ₄ ring in the formula (1) are condensed with each other, and each of the A ₁ ring and the A ₂ ring is fused to each other by sharing carbon atoms in adjacent five-member rings. Each of the A ₁₁ ring and the A ₁₂ ring in Formula 2 is fused to each other by sharing carbon atoms in adjacent six-member rings.

The A ₁ ring, the A ₂ ring, the A ₄ ring, the A ₁₁ ring and the A ₁₂ ring in the above-mentioned formulas (1) and (2) independently of one another are a C ₅ -C ₃₀ carbocyclic group and a C ₂ -C ₃₀ heterocyclic group Can be selected.

For example, the A ₁ ring, the A ₂ ring and the A ₄ ring in the above formulas (1) and (2) independently of one another are selected from the group consisting of benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, quinoxaline, quinazoline, ≪ / RTI >

The A ₁₁ ring and the A ₁₂ ring are each independently selected from the group consisting of naphthalene, heptalene, phenalene, phenanthrene, anthracene, triphenylene, pyrene, klysene, naphthacene, picene, perylene, pentaphen, quinoline, isoquinoline , Quinoxaline, quinazoline, cinnoline, naphthyridine, acridine and phenanthroline.

According to one embodiment, the A ₁ ring, the A ₂ ring and the A ₄ ring in the above formulas (1) and (2) are independently selected from benzene and naphthalene,

The A ₁₁ ring and the A ₁₂ ring may be independently selected from among naphthalene, heptalene, phenalene, phenanthrene, anthracene, triphenylene, pyrene, klysene, naphthacene, picene, perylene and pentaphen .

According to another embodiment, the A ₁ ring, the A ₂ ring and the A ₄ ring in the above formulas (1) and (2) are benzene, and the A ₁₁ ring and the A ₁₂ ring may be independently selected from naphthalene and phenanthrene.

The A ₃ ring in Formula 1 may be selected from the group represented by Formula 1-1.

X ₁ in the general formulas (1) and (1-1) may be O or S, and X ₂ may be selected from N - [(L ₂ ) a ₂ - (R ₁ ) _{b 1} ], O and S. Here, the description of L ₂ , a 2, R _1, and b ₁ is as described in this specification.

According to one embodiment, the formula (1) X ₂ are N and 1-1 of the - _[(2 L) _a2 - ₍₁ R) _b1] a, and X ₁₁ is N, X is _12, or C (R _12), X ₁₁ is C (R ₁₁ ), and X ₁₂ can be N.

X ₁₁ in Formula 1 is selected from N and C (R ₁₁ ), X ₁₂ is selected from N and C (R ₁₂ ), and at least one of X ₁₁ and X ₁₂ may be N. Here, the description of R ₁₁ and R ₁₂ is as described in this specification.

L ₁ to L ₅ and L ₂₁ to L ₂₃ in the general formula (1), (1-1) and (2) are, independently of each other, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, Or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group ) And a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group (substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group).

For example, L ₁ to L ₅ and L ₂₁ to L ₂₃ in the above general formulas (1), (1-1) and (2)

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, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, and ovalenyl (hereinafter referred to as "ovalenyl"), perylenylene, pentaphenylene, pentacenylene, pentacenylene, Ovalenylene, pyrrolylene group (pyr a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, 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, ), Acrylidynylene group ( The present invention relates to a process for the production of isobenzothiazolylene (hereinafter abbreviated as "acridinylene"), acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, 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, an anthracenyl group, a fluoranthenyl group, a triphenylthienyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, a thiophenyl group, An imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, isoxazolyl 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, A phenylene group, a phenylene group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) A naphthylene group, an azulenylene group, a heptalenylene group, 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.

According to one embodiment, L ₁ to L ₅ and L ₂₁ to L ₂₃ in the general formulas (1), (1-1) and (1-2) are independently selected from the group consisting of the following formulas Can be:

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 another embodiment, L ₁ to L ₅ and L ₂₁ to L ₂₃ in the general formulas (1), (1-1) and (2) are independently selected from the group consisting of the following formulas have:

In the above formulas (4-1) and (4-36), * and * are binding sites with neighboring atoms.

A1 to a5 and a21 to a23 in formulas (1), (1-1) and (1-2) may be independently selected from the integers of 0 to 5. If a1 is 0, _{* - (L 1) a1 -} * ' is a single bond, when a1 is 2 or more, two or more L ₁ is the same as or different from each other. The description of the above a2 to a5 and a21 to a23 can be understood with reference to the structures of the above formulas (1), (1-1) and (2) and the description of the above a1.

According to one embodiment, a1 to a5 and a21 to a23 in the above formulas (1), (1-1) and (1-2) may be independently 0 or 1.

R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in the general formula (1), (1-1) and (2) independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic group, C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -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 A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group, a substituted addition It is unsubstituted 1 non-aromatic heterocyclic condensed polycyclic _{group, Si (Q 1) (Q} 2) (Q 3), -N (Q 1) (Q 2), -B (Q 1) (Q 2), - Q (= O) (Q ₁ ), -S (= O) ₂ (Q ₁ ) and -P (= O) (Q ₁ ) (Q ₂ ).

For example, R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in the general formulas (1), (1-1) and (2) independently of one another are hydrogen, deuterium, -F, -Cl, -Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, Or 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 monovalent non-aromatic A heterocyclic polycyclic group, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ).

According to one embodiment, R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in the general formula (1), (1-1) and (2)

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;

Substituted with at least one of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, an indacenyl group, an acenaphthyl group, ), Fluorenyl, spiro-fluorenyl, spiro-cycloheptane-fluorenyl, spiro-cyclohexane-fluorenyl, benzofluorenyl, dibenzofluorenyl, a phenanthrenyl 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 picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group a thiophenyl group, a pyrrolyl group, a thiophenyl group, a thiophenyl group, And examples thereof include furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyrimidyl, And examples thereof include pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furyl group, a quinolinyl group such as purinyl, sillolyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, Quinazolinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenanthrolinyl, phenanthrolinyl, Phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isocyanates such as benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, ), A triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyldibenzoylsilyl group, a thiadiazolyl group, an imidazopyridinyl group And an imidazopyrimidinyl group;

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, Cycloheptane-fluorenyl group, a benzo-fluorenyl group, a dibenzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylguanyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylrryanyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group , Rubicenyl group, coronenyl group, ovalenyl group, phenoxy group, phenylthio group, pyrrolyl group, thiophenyl group An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a pyrazolyl group, A naphthyridinyl group, a quinazolinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, an imidazolyl group, an indolyl group, an indolyl group, a pyridyl group, a silolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, A benzothiophene group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an isobenzoxazolyl group, a triazinyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, A thiazolyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, a thiazolyl group, an imidazolidinyl group, of the pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) enemy A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenyl-cyclohexane-fluorenyl group, a spiro-cyclohexane-fluorenyl group, A phenylene group, a phenacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a phenoxyl group, a pyrrolyl group, a pyrrolyl 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 furyl group, a silyl group A quinolinyl group, a quinolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, A phenanthrolinyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, , Triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyldibenzoylsilyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl 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 ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ in the general formula (1), (1-1) and (2)

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, a C ₁ -C ₁₀ An alkoxy group, a group represented by the following formulas (5-1) to (5-75); And _{-Si (Q 1) (Q 2} ) (Q 3) is selected from the Q ₁ to Q ₃ are independently of one another, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, A terphenyl group and a naphthyl group:

Of the above-mentioned formulas (5-1) to (5-75)

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

Z ₃₁ to Z ₃₇ are, 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-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, A pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a pyrazinyl group, a pyrazinyl group, selected from triazinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) , and,

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,

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,

e7 is selected from integers from 1 to 7,

e8 is selected from integers from 1 to 8,

and e9 is selected from integers from 1 to 9.

According to another embodiment, in the above formulas (1), (1-1) and (2)

R ₂ to R ₄ , R ₂₂ and R ₂₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, selected from crude hydrazine group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 1) (Q 2} ) (Q 3) and,

R _1, R ₁₁ to R ₁₃ and R ₂₁ are, each independently, to groups and to be represented by the formula 6-1 to 6-43 is selected from the group represented by the formula 10-1 to 10-117, wherein Q ₁ together To Q ₃ 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 formulas (6-1) to (6-43) and (10-1) to (10-117), * denotes a binding site with neighboring atoms.

According to another embodiment, the compounds of formulas (1), (1-1) and (2)

R ₂ to R ₄ , R ₂₂ and R ₂₃ are hydrogen,

R ₁ , R ₁₁ to R ₁₃ and R ₂₁ are independently of each other a group represented by the above formulas 5-1 to 5-75 (for example, the formulas 6-1 to 6-43 and the formulas 10-1 to 10- 117), but the present invention is not limited thereto.

B1 to b4 and b21 to b23 in the above formulas (1), (1-1) and (2) may be independently selected from integers of 0 to 4. b1 represents the number of R ₁ in the formula (2), and when b1 is 2 or more, two or more R ₁ may be the same or different. The description of b2, b3 and b21 to b23 can be understood with reference to the structures of the above formulas (1), (1-1) and (2) and the description of b1.

According to one embodiment, b1 to b4 and b21 to b23 in the above formula (1) may be independently 0, 1 or 2, or 0 or 1, but is not limited thereto.

C1 to c3, c22 and c23 in the above formulas (1), (1-1) and (2) can be independently selected from an integer of 0 to 10. c1 is of the formula 1 * - 2 or more, if c1 is 2 or more as shown the number of _{- [(L 2) a2 (} R 1) b1] * - [(L 2) a2 - (R 1) b1] is another May be the same or different. c2, c3, c22 and c23 can be understood with reference to the structures of the above formulas (1), (1-1) and (2) and the description of the above c1.

According to one embodiment, for example, c1 to c3, c22 and c23, independently of each other, may be 0 or 1, but are not limited thereto.

According to one embodiment, the first compound may be represented by one of the following Formulas 1A-1F, but is not limited thereto:

The descriptions of the A ₁ ring, the A ₄ ring, X ₁ , X ₂ , X ₁₁ , X ₁₂ , L ₁ , a ₁ , R ₂ to R ₄ , R ₁₃ and b ₂ to b _{4 in the} above formulas See the description.

According to another embodiment, the first compound is selected from the group consisting of compounds represented by the following formulas 1A-1, 1A-2, 1B-1, 1B-2, 1C-1, 1C-2, 1D-1, 1D-2, 1E- -2, 1F-1 and 1F-2, but are not limited to:

1E-1, 1E-2, 1B-2, 1C-1, 1C-2, 1D-1, 1D- The descriptions of X ₁ , X ₂ and R ₁₃ are as described herein.

1E-1, 1B-2, 1C-1, 1C-2, 1D-1, 1D-2, 1E-1, 1E- 1 and 1F-2

X ₁ is O or S, X ₂ is N (R ₁ )

R ₁ and R ₁₃ may be independently selected from the group represented by the above Formulas 6-1 to 6-43 and the groups represented by the above Formulas 10-1 to 10-117.

According to one embodiment, the second compound may be represented by one of the following formulas (2A) to (2I):

≪ RTI ID = 0.0 >

The description of L ₂₁ , a21, R ₂₁ to R _24, and b21 to b24 will be referred to herein as described,

For a description of R _22a and R _22b , reference is made to the discussion of R ₂₂ in this specification,

For a description of R _23a and R _23b , reference is made to the description of R ₂₃ in this specification,

and Ba 22 and Ba 23 are independently selected from integers of 0 to 6,

bb22 and bb23 are independently selected from the integers of 0 to 4;

According to another embodiment, the second compound is a compound of formula 2A-1, 2A-2, 2B-1, 2B-2, 2C-1, 2C-2, 2D-1, 2D-2, 2E- 2, 2F-1, 2F-2, 2G-1, 2G-2, 2H-1, 2H-2, 2I-1 and 2I-2.

2E-1, 2E-2, 2F-1, 2F-2, 2F-2, of 2G-1, 2G-2, 2H-1, 2H-2, 2I-1 and 2I-2, L ₂₁ and For a description of R ₂₁ , see what is described herein.

2E-2, 2F-1, 2E-2, 2E-1, 2E-2, 2F-2, 2G-1, 2G-2, 2H-1, 2H-2, 2I-

L ₂₁ is selected from the group of the formulas (4-1) to (4-36)

R ₂₁ may be selected from the group of the formulas (6-1) to (6-43) and the groups represented by the following formulas (10-1) to (10-117).

According to one embodiment, the first compound is one of the following compounds H1 to H8, and the second compound is one of the following compounds ET1 to ET12, but is not limited thereto:

For example, the first electrode of the organic light emitting device may be an anode, and the second electrode may be a cathode. The organic layer may include i) a hole injection layer, a hole transport layer, And a hole transporting region including at least one of an electron blocking layer and an electron blocking layer, and ii) an electron transporting region interposed between the light emitting layer and the second electrode, the electron transporting region including at least one of a hole blocking layer, .

According to one embodiment, the first compound is contained in the light emitting layer, and the second compound is contained in the electron transporting region.

According to another embodiment, the electron transporting region includes an electron transporting layer, the first compound is contained in the light emitting layer, and the second compound is contained in the electron transporting layer.

The first compound represented by the formula (1) is obtained by condensation of carbazole with indole, benzofuran or benzothiophene, and introducing a 5-membered heterocycle containing N, O and S into the nitrogen atom of the carbazole, It is possible to control the electron balance in the organic molecules while maintaining the main skeleton. Accordingly, the organic light emitting device including the first compound represented by Formula 1 can have low driving voltage, high efficiency, high brightness, and long life.

The second compound represented by the general formula (2) has a condensed ring core based on acridine. Therefore, since the organic compound is enriched in electrons by the nitrogen atom and has a strong molecular structure, the organic light emitting device including the second compound represented by the formula (2) can have a long life.

In addition, since the light emitting layer of the organic light emitting device includes the first compound represented by Formula 1 as described above and the electron transport layer of the organic light emitting device includes the second compound represented by Formula 2, The movement balance of the holes and electrons is balanced, the efficiency at low voltage is improved by the excellent hole injection characteristic and the electron injection characteristic, and thus the low driving voltage and high efficiency of the organic light emitting device can be achieved.

The first compound represented by Formula 1 and the second compound represented by Formula 2 may be synthesized using a known organic synthesis method. The method for synthesizing the first compound and the second compound can be recognized by those skilled in the art with reference to the following examples.

In the present specification, "first compound" means i) only one compound (for example, compound H1) belonging to the category of the formula 1, or ii) two or more different compounds belonging to the category 1 May mean a mixture (e. G., A mixture of compounds H1 and H2).

In the present specification, "second compound" means i) only one compound (for example, compound ET1) belonging to the category of formula 2 above, or ii) two or more different compounds belonging to the category of formula 2 (E. G., A mixture of compounds ET1 and ET2).

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. < / RTI >

 [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 be at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB (NPD), beta-NPB, TPD, Spiro-TPD, Spiro- NPB, methylated -NPB, TAPC, HMTPD, , 4 "-tris (N-carbazolyl) triphenylamine (4,4 ', 4" -tris (N-carbazolyl) triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid) , Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Polyaniline / poly (4-styrenesulfonate), PANI / PSS (polyaniline / poly (4-styrenesulfonate)), a compound represented by the following formula (201) At least one selected from the group consisting of:

≪ Formula 201 >

≪ 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 < 5 > 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 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;

≪ / 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.

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;

, ≪ / RTI >

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:

≪ 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.

[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 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 cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, A naphthyl group, a naphthyl group, a pyridazinyl group, a triazinyl group, a pyridazinyl group, a triazinyl group, a pyridazinyl group, a triazinyl group, a pyridazinyl group, a triazinyl 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 member 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.

According to one embodiment, the electron transport region may comprise a second compound as described above. According to another embodiment, the electron transporting region comprises an electron transporting layer, and the electron transporting layer may comprise the second compound.

Alternatively, the electron transporting region may contain, in addition to the second compound, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7- _3, BAlq, the TAZ 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, 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, which is an electron injection electrode. The material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, combinations 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 A vacuum of ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 A / sec, taking into account the material to be included in the layer to be formed and the structure of the layer to be formed.

When each layer included in the hole transporting region, the light emitting layer and the electron transporting region are 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 Can be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed within the 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 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydro A thiophenyl 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, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, 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 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]

Synthesis Example 1: Synthesis of Compound H1

Synthesis of intermediate I-2

178.6 mg (0.20 mmol) of Pd ₂ (dba) ₃ and 78.9 mg (0.39 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-xylene and stirred at room temperature for 10 minutes. 5 g (19.51 mmol) of 5,11-dihydroindolo [3,2-b] carbazole, 3.37 g (21.46 mmol) of bromobenzene and 1.12 g (11.71 mmol) of t- At reflux for 48 hours. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 5.62 g (yield 87%) of intermediate I-2 (5-phenyl-5,11-dihydroindolo [3,2- b] carbazole) was obtained through column chromatography. EI-MS, m / e, 332.13 (calcd.), 332.18 (found).

Synthesis of Compound H1

137.7 mg (0.15 mmol) of Pd ₂ (dba) ₃ and 60.8 mg (0.30 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-xylene and stirred at room temperature for 10 minutes. 5.23 g (16.55 mmol) of 5-bromo-2,4-diphenyloxazole and 0.867 mg (9.03 mmol) of t-BuONa were added to 5 g (15.04 mmol) of Intermediate I-2 and refluxed for 48 hours at 160 ° C . After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 7.32 g (yield 86%) of a compound H1 (2,4-diphenyl-5- (11-phenylindolo [3,2- b] carbazol-5 (11H) -yl) thiazole was obtained through column chromatography. EI-MS, m / e, 475.17 (calcd.), 475.37 (found).

Synthesis Example 2 : Synthesis of Compound H2

Synthesis of intermediate V-2

393 mg (0.43 mmol) of Pd ₂ (dba) ₃ and 118 mg (0.59 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. (19.51 mmol), 2-bromopyridine (6.47 g, 40.97 mmol), and t-BuONa (2.25 g, 23.41 mmol) The mixture is refluxed for 48 hours and stirred. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 5.01 g (yield 77%) of Intermediate V-2 (5- (pyridin-2-yl) -5,11-dihydroindolo [3,2- b] carbazole) was obtained through column chromatography. EI-Ms, m / e, 333.13 (calc.), 333.21 (found).

Synthesis of Compound H2

151 mg (0.16 mmol) of Pd ₂ (dba) ₃ and 46 mg (0.22 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. 5 g (14.99 mmol) of 5-bromo-2-phenylthiazole and 1.98 g (8.25 mmol) of V- 2 (5- (pyridin- 2- yl) -5,11- dihydroindolo [3,2- -BuONa (0.86 g, 8.99 mmol) was added, and the mixture was stirred under reflux at 160 캜 for 48 hours. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 6.24 g (yield 84%) of compound H2 (2-phenyl-5- (11- (pyridin- 2- yl) indolo [ ). EI-Ms, m / e, 492.14 (calc.), 492.22 (found).

Synthetic example  3 : Synthesis of Compound H6

Synthesis of Intermediate VI-2

393 mg (0.43 mmol) of Pd ₂ (dba) ₃ and 118 mg (0.59 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. , 6.47 g (40.97 mmol) of 4-bromopyridine and 2.25 g (23.41 mmol) of t-BuONa were added to the reaction mixture at 160 ° C The mixture is refluxed for 48 hours and stirred. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 5.31 g (yield 82%) of Intermediate VI-2 (5- (pyridin-4-yl) -5,11-dihydroindolo [3,2- b] carbazole) was obtained through column chromatography. EI-Ms, m / e, 333.13 (calc.), 333.23 (found).

Synthesis of Compound H6

151 mg (0.16 mmol) of Pd ₂ (dba) ₃ and 46 mg (0.22 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. , 1.98 g (8.25 mmol) of 5-bromo-2-phenylthiazole, and 5 g (8.99 mmol) of 5-bromo-2- -BuONa (0.86 g, 8.99 mmol) was added, and the mixture was stirred under reflux at 160 캜 for 48 hours. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 6.53 g (yield 88%) of the compound H6 (2-phenyl-5- (11- (pyridin-4-yl) indolo [3,2- ). EI-Ms, m / e, 492.14 (calc.), 492.25 (found).

Synthesis Example 4 : Synthesis of Compound ET1

Synthesis of Compound ET1

109 mg (0.12 mmol) of Pd ₂ (dba) ₃ and 33 mg (0.16 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. (10.91 mmol) of the starting material V-1 (18-bromotetrabenzo [a, c, h, j] acridine), 1.88 g (11.99 mmol) of bromobenzene, and 0.63 g (6.54 mmol) of t- The mixture is refluxed for 48 hours and stirred. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 4.14 g (yield: 83%) of compound ET1 (18-phenyltetrabenzo [a, c, h, j] acridine) was obtained through column chromatography. EI-MS, m / e, 455.17 (calc.), 455.25 (found).

Synthesis Example 5 : Synthesis of Compound ET3

Synthesis of intermediate VII-2

219 mg (0.24 mmol) of Pd ₂ (dba) ₃ and 66 mg (0.33 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. 5.90 g (22.90 mmol) of 1,4-dibromobenzene and 1.25 g (13.09 mmol) of t-BuONa were added to 160 ml of a solution of 160 &Lt; / RTI &gt; and stirred at reflux for 48 hours. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 4.13 g (yield: 71%) of Intermediate VII-2 (18- (4-bromophenyl) tetrabenzo [a, c, h, j] acridine) was obtained through column chromatography. EI-Ms, m / e, 533.08 (calc.), 533.15 (found).

Synthesis of Compound ET3

75 mg (0.08 mmol) of Pd ₂ (dba) ₃ and 23 mg (0.11 mmol) of t-Bu ₃ P were dissolved in 40 ml of o-Xylene and stirred at room temperature for 10 minutes. 4,4 g (7.48 mmol) of 8- (4-bromophenyl) tetrabenzo [a, c, h, j] acridine, 0.97 g (4.12 mmol) of 9-bromoanthracene, and 0.43 g (4.49 mmol) of t- And the mixture was refluxed at 160 DEG C for 48 hours and stirred. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 4.21 g (yield 89%) of compound ET3 (18- (4- (anthracen-9-yl) phenyl) tetrabenzo [a, c, h, j] acridine was obtained through column chromatography. EI-Ms, m / e, 631.23 (calc.), 631.16 (found).

Synthesis Example 6 : Synthesis of Compound ET10

Synthesis of intermediate VIII-2

281 mg (0.31 mmol) of Pd ₂ (dba) ₃ and 84 mg (0.42 mmol) of t-Bu ₃ P were dissolved in 50 ml of o-Xylene and stirred at room temperature for 10 minutes. 6.91 g (29.31 mmol) of 1,4-dibromobenzene and 1.61 g (16.74 mmol) of t-BuONa were added and the mixture was stirred at 160 ° C. for 48 hours Lt; / RTI &gt; and stirred. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 4.81 g (yield 79%) of Intermediate VIII-2 (7- (4-bromophenyl) dibenzo [c, h] acridine) was obtained through column chromatography. EI-Ms, m / e, 433.05 (calc.), 433.14 (found).

Synthesis of Compound ET10

After dissolving 92 mg (0.10 mmol) of Pd ₂ (dba) ₃ and 27 mg (0.14 mmol) of t-Bu ₃ P in 40 ml of o-xylene, the mixture was stirred at room temperature for 10 minutes. (5.06 mmol) of 8-bromoquinoline and 0.53 g (5.53 mmol) of t-BuONa were added to the solution, and the mixture was heated to 160 ° C At reflux for 48 hours. After completion of the reaction, 20 ml of cold distilled water is added and extracted with ethylacetate. After drying with Magnessium sulfate, the solvent is evaporated. Thereafter, 3.24 g (yield: 73%) of compound ET10 (7- (4- (quinolin-8-yl) phenyl) dibenzo [c, h] acridine was obtained through column chromatography. EI-Ms, m / e, 482.18 (calc.), 482.25 (found).

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.

2-TNATA was vacuum-deposited on the ITO anode to form a hole injection layer having a thickness of 600 A, and NPB was vacuum-deposited on the hole injection layer to form a hole transporting layer having a thickness of 300 A to form a hole transporting region.

Compound H1 (host) and PD9 (dopant) were co-deposited on the hole transporting region at a weight ratio of 87: 13 to form a 300Å thick light emitting layer.

The electron transport layer was deposited on the emission layer to form a 300 Å electron transport layer. LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al was vacuum deposited on the electron injection layer to form a 3000 Å thick To form an organic light emitting device.

Examples 2 and 3 and Comparative Examples 1 to 3

An organic light emitting device was prepared in the same manner as in Example 1 except that the compound described in Table 1 was used instead of the compound H1 and / or the compound ET1 in forming the light emitting layer and / or the electron transporting layer.

Evaluation example 1

The driving voltage, luminance and efficiency of the organic light emitting devices fabricated in Examples 1 to 3 and Comparative Examples 1 to 3 were measured using a Keithley SMU 236 and a luminance meter PR650, and the results are shown in Table 1.

Emitting layer host Electron transport layer Driving voltage
(V) Luminance
(cd / m ² ) efficiency
(cd / A) Example 1 Compound H1 Compound ET1 4.7 1000 16.8 Example 2 Compound H2 Compound ET3 4.6 1000 17.1 Example 3 Compound H6 Compound ET10 4.5 1000 16.9 Comparative Example 1 CBP Alq ₃ 7.8 1000 11.1 Comparative Example 2 Compound A1 Compound B1 5.5 1000 15.8 Comparative Example 3 Compound A2 Compound B2 5.6 1000 16.1

It can be seen from Table 1 that the driving voltage and efficiency of the organic light emitting devices of Examples 1 to 3 are superior to the driving voltage and efficiency of the organic light emitting devices of Comparative Examples 1 to 3.

10, 20, 30, 40: Organic light emitting device
110: first electrode
150: organic layer
190: second electrode
210: first capping layer
220: second capping layer

Claims (20)

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;
/ RTI &gt;
Wherein the organic layer comprises a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2:
&Lt; Formula 1 &gt;

&Lt; Formula 1-1 &gt;

(2)

In the above formulas (1), (1-1) and (2)
The A ₂ ring, the A ₃ ring and the A ₄ ring are condensed with each other,
The A ₁ ring, the A ₂ ring, the A ₄ ring, the A ₁₁ ring and the A ₁₂ ring are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₂ -C ₃₀ heterocyclic group,
The A ₃ ring is selected from the group represented by the formula (1-1)
X &lt; ₁ &gt; is O or S,
X ₂ is selected from N - [(L ₂ ) a ₂ - (R ₁ ) _{b 1} ], O and S,
X ₁₁ is selected from N and C (R ₁₁ ), X ₁₂ is selected from N and C (R ₁₂ ), at least one of X ₁₁ and X ₁₂ is N,
L ₁ through L ₅ and L ₂₁ to L ₂₃ are, each independently, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ to each other -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenylene 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 divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non- - selected from substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic groups,
a1 to a5 and a21 to a23 are each independently selected from an integer of 0 to 5,
R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano 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 ₂ -C ₆₀ alkenyl group, An unsubstituted C ₁ -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 cycloalkane Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic Condensed polycyclic heterocyclic _{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 )
b1 to b4 and b21 to b23 are independently selected from integers of 0 to 4,
c1 to c3, c22 and c23 are each independently selected from integers from 0 to 6,
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 hydrocarbon ring, at least one of the substituents of the fused 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 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, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl 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 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,
The A ₁ ring, the A ₂ ring and the A ₄ ring are independently selected from among benzene and naphthalene,
The A ₁₁ ring and the A ₁₂ ring are each independently selected from naphthalene and phenanthrene. The method according to claim 1,
X ₂ is N - [(L ₂ ) a ₂ - (R ₁ ) _{b 1} ]. The method according to claim 1,
X ₁₁ is N, X ₁₂ is C (R ₁₂ )
X ₁₁ is C (R ₁₁ ), and X ₁₂ is N. The method according to claim 1,
L ₁ to L ₅ and L ₂₁ to L ₂₃ independently of one another,
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, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, and ovalenyl (hereinafter referred to as "ovalenyl"), perylenylene, pentaphenylene, pentacenylene, pentacenylene, Ovalenylene, pyrrolylene group (pyr a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, 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, ), Acrylidynylene group ( The present invention relates to a process for the production of isobenzothiazolylene (hereinafter abbreviated as "acridinylene"), acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, 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, An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylguanyl group, a pyrenyl group, a chrycenyl group, a pyrenyl group, a pyrazolyl group, A thiophene group, a furanyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl 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, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazolyl 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 quinoxaline group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isothiazolyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiazolyl group, a thiazolyl group, oxadiazole group, imidazolidin jopi piperidinyl group, an already substituted by at least one of the imidazo pyrimidinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33), a phenylene group, pental alkylenyl group, an indenyl group, a naphthyl group , Azulenylene group, heptarenylene group, indacenylene group, acenaphthyl A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrene group, a phenanthrene group, a fluorenylene group, a spiro-fluorenylene group, , A pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentachenylene group, a rubicecylene group, a coronenylene group, A thiophenylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, And examples thereof include a pyridazinyl group, a pyridazinyl group, an isoindolylene group, an indolylene group, an indazolylene group, a pyrinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, A salenylene group, a quinazolinylene group, , A carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group , A benzooxazolyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolyl group, a dibenzocarbazolyl group, Imidazopyridinylene group and imidazopyrimidinylene group; &Lt; / RTI &gt;
Wherein 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. The method according to claim 1,
L ₁ to L ₅ and L ₂₁ to L ₂₃ 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,
L ₁ to L ₅ and L ₂₁ to L ₂₃ are each independently selected from the group consisting of the following formulas (4-1) to (4-36).

In the above formulas (4-1) to (4-36), * and * are binding sites with neighboring atoms. The method according to claim 1,
a1 to a5 and a21 to a23 are independently of each other, 0 or 1. The method according to claim 1,
R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ 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 ₁ -C ₂₀ alkoxy group, unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent ring non-fused polycyclic aromatic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic group, and -Si (Q ₁₎ (Q ₂ ) (Q ₃ ). The method according to claim 1,
R ₁ to R ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ independently of one another,
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;
Substituted with at least one of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazino group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, an indacenyl group, an acenaphthyl group, ), A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, Examples of the substituent include fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaerythritol, A substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentacenyl group, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl (t isoxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoxazolyl, isothiazolyl, isoxazolyl, isoxazolyl, isoxazolyl, pyrazinyl, pyrazinyl, pyrazinyl, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a sillolyl group, a quinolinyl group, an isoquinolinyl group, an isoquinolinyl 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 phenanthridinyl group such as phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group benzothiophenyl, isobenzothiazolyl, benzooxyl, azolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, A dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyldibenzoylsilyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
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, an anthracenyl group, a fluoranthenyl group, a triphenylthienyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A phenanthryl group, a phenanthryl group, a pyrenyl group, a pyrenyl group, a klycenyl 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, A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, A pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a silyl group, a quinolinyl group, an isoquinolinyl group, A phenanthrolinyl group, a phenazinyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzofuranyl group, a benzothiopyranyl group, a benzothiophenol group, Substituted with at least one of -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), benzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and -Si A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, Anthracenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthryl group, phenanthryl group, phenanthryl group, phenanthryl group, A naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronene group, a fluorenyl group, a fluorenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazolyl group, a pyrazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a silyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, A quinazolinyl group, a quinazolinyl group, a cyano group, a carbazolyl group, A benzothiophene group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, A thiadiazolyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazolidinyl group, an imidazolidinyl group, an imidazolidinyl group, A pyrimidinyl 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 ₄ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ independently of one another,
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, a C ₁ -C ₁₀ An alkoxy group, a group represented by the following formulas (5-1) to (5-75); And _{-Si (Q 1) (Q 2} ) (Q 3) is selected from the Q ₁ to Q ₃ are independently of one another, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, A terphenyl group, and a naphthyl group;

Of the above-mentioned formulas (5-1) to (5-75)
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or Si (Z ₃₆ ) (Z ₃₇ );
Z ₃₁ to Z ₃₇ are, 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-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, A pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a pyrazinyl group, a pyrazinyl group, selected from triazinyl group and a _{-Si (Q 31) (Q 32} ) (Q 33) , and,
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,
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,
e7 is selected from integers from 1 to 7,
e8 is selected from integers from 1 to 8,
e9 is selected from integers from 1 to 9,
* Is the binding site with neighboring atoms. The method according to claim 1,
R ₂ to R ₄ , R ₂₂ and R ₂₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, selected from crude hydrazine group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 1) (Q 2} ) (Q 3) and,
R _1, R ₁₁ to R ₁₃ and R ₂₁ are, each independently, to groups and to be represented by the formula 6-1 to 6-43 is selected from the group represented by the formula 10-1 to 10-117, wherein Q ₁ together To Q ₃ 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.

In Formulas 6-1 to 6-64 and 10-1 to 10-117, * denotes a binding site with neighboring atoms. The method according to claim 1,
Wherein the first compound is represented by one of the following formulas (1A) to (1F):

The description of the A ₁ ring, the A ₄ ring, X ₁ , X ₂ , X ₁₁ , X ₁₂ , L ₁ , a ₁ , R ₂ to R ₄ , R ₁₃ and b ₂ to b ₄ in the above- Lt; / RTI &gt; The method according to claim 1,
Wherein the first compound is a compound represented by any of the following Formulas 1A-1, 1A-2, 1B-1, 1B-2, 1C-1, 1C-2, 1D-1, 1D-2, 1E- And 1F-2.

1E-1, 1E-2, 1B-2, 1C-1, 1C-2, 1D-1, 1D- X ₁ , X ₂ , R ₁₂ and R ₁₃ are the same as described in the above item 1. The method according to claim 1,
Wherein the second compound is represented by one of the following formulas (2A) to (2I):

&Lt; RTI ID = 0.0 &gt;
L ₂₁ , a21, R ₂₁ to R ₂₄ and b ₂₁ to b ₂₄ are as defined in claim 1,
The description of R _22a and R _22b refers to the description of R ₂₂ in the first paragraph,
The description of R _23a and R _23b refers to the description of R ₂₃ in the first paragraph,
and Ba 22 and Ba 23 are independently selected from integers of 0 to 6,
bb22 and bb23 are independently selected from the integers of 0 to 4; The method according to claim 1,
Wherein the second compound is a compound of Formula 2A-1, 2A-2, 2B-1, 2B-2, 2C-1, 2C-2, 2D-1, 2D-2, 2E-1, 2E- , 2F-2, 2G-1, 2G-2, 2H-1, 2H-2, 2I-1 and 2I-

2E-1, 2E-2, 2F-1, 2F-2, 2F-2, of 2G-1, 2G-2, 2H-1, 2H-2, 2I-1 and 2I-2, L ₂₁ and The description of R ₂₁ is the same as that described in claim 1. The method according to claim 1,
Wherein the first compound is one of the following compounds H1 to H8, and the second compound is one of the following compounds ET1 to ET12:

The method according to claim 1,
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 injecting layer, a hole transporting layer, a light emitting assisting layer and an electron blocking layer, and ii) And an electron transport region including at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer. 19. The method of claim 18,
Wherein the light emitting layer contains the first compound,
Wherein the electron transporting region comprises an electron transporting layer,
And the second compound is contained in the electron transport layer. 20. The method of claim 19,
Wherein the light emitting layer comprises an organometallic complex represented by Formula 401 below:
&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).

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