KR20170047653A - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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KR20170047653A
KR20170047653A KR1020150148023A KR20150148023A KR20170047653A KR 20170047653 A KR20170047653 A KR 20170047653A KR 1020150148023 A KR1020150148023 A KR 1020150148023A KR 20150148023 A KR20150148023 A KR 20150148023A KR 20170047653 A KR20170047653 A KR 20170047653A
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김민경
이재용
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삼성디스플레이 주식회사
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    • H01L51/0052
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20Polycyclic condensed hydrocarbons
    • C07C15/24Polycyclic condensed hydrocarbons containing two rings
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20Polycyclic condensed hydrocarbons
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    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1003Carbocyclic compounds
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Abstract

Disclosed is an organic light emitting device with high efficiency and excellent durability. The organic light emitting device comprises: a first electrode; a second electrode opposite to the first electrode; and an organic layer interposed between the first electrode and the second electrode, including a light emitting layer.

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 to provide an organic light emitting device having high efficiency and long life.

According to one aspect,

A first electrode;

A second electrode facing the first electrode; And

And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer,

Wherein the organic layer comprises a first compound and a second compound,

Wherein the first compound is selected from compounds represented by the following general formula (1)

Wherein the second compound is selected from compounds represented by the following Chemical Formulas 2A and 2B:

≪ Formula 1 >

Figure pat00001

≪ Formula 1-1 >

Figure pat00002

≪ Formula 2A >

Figure pat00003

(2B)

Figure pat00004

≪ Formula (2-1)

Figure pat00005

Among the above Chemical Formulas 1, 1-1, 2A, 2B and 2-1,

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

m1 is selected from integers from 1 to 3,

X 21 , X 31 and X 32 are independently of each other O or S,

L 1 to L 3 , L 21 , L 31 and L 41 independently represent a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, 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 1 - C 60 heteroaryl group, an unsubstituted 2-substituted or unsubstituted non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non-aromatic hydrocarbon ring condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

a1 to a3, a21, a31 and a41 are each independently selected from an integer of 0 to 3,

Ar 21 , Ar 41 and Ar 42 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 A substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted aryl group, Aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups,

R 1 to R 3 , R 11 and R 21 to R 50 independently of one another are a group represented by the above formula (2-1), hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C 1 -C 60 alkyl group, A substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted Or a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 10 heterocycloalkyl group, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic group and the condensed polycyclic -Si (Q 1) (Q 2 ) (Q 3 ), ≪ / RTI >

c1 and c2 are each independently selected from an integer of 0 to 4,

c11 is selected from an integer of 0 to 7,

n1 is selected from integers from 1 to 3, n2 is selected from integers from 0 to 8, n3 is selected from integers from 0 to 7,

At least one of R 21 to R 30 is selected from the group represented by the above formula (2-1)

* Is the binding site with neighboring atoms,

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy groups (aryloxy), C 6 -C 60 arylthio group (arylthio), 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) and -N (Q 14) (Q 15 ) of the at least one substituted, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, 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 hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 - C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -Si (Q 21) (Q 22) (Q 23) and -N (Q 24) (Q 25 ) C 1 -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 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, 1 Aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

-Si (Q 31) (Q 32 ) (Q 33) and -N (Q 34) (Q 35 ); ;

Wherein Q 1 to Q 3 , Q 11 to Q 15 , Q 21 to Q 25 and Q 31 to Q 35 are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or its salt, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl A C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

The organic light emitting diode may have a low driving voltage and a high efficiency.

1 is a schematic view showing the structure of an organic light emitting device according to an embodiment.

1 is a schematic view showing a cross section of an embodiment of the organic light emitting device.

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

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 materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), or the like is used as the first electrode material for forming the first electrode 3 which is a translucent electrode or a reflective electrode. ), Magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

The first electrode 110 may have a single layer or a multilayer 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.

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

Wherein the first compound is selected from compounds represented by the following general formula (1), and the second compound is selected from compounds represented by the following general formulas (2A) and (2B) :

≪ Formula 1 >

Figure pat00006

≪ Formula 2A >

Figure pat00007

(2B)

Figure pat00008

R 1 to R 3 , R 11 and R 21 to R 50 in the general formulas (1), (2) and (2B) are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxy group, a substituted or unsubstituted C 1 -C 6 alkoxy group, -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C A substituted or unsubstituted C 1 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, A substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio Group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic group and the condensed polycyclic -Si (Q 1 ) (Q 2 ) (Q 3 ).

≪ Formula (2-1)

Figure pat00009

In the above general formula (2-1), L 41 , a 41 , Ar 41 and Ar 42 are as described in the present specification, and * is a bonding site with neighboring atoms.

At least one of R 21 to R 30 in Formula 2A is selected from the group represented by Formula 2-1.

In the above formula (1), A 1 may be selected from the group represented by the following formula (1-1)

≪ Formula 1-1 >

Figure pat00010

In the above formula (1-1), R 11 and c 11 are the same as described in the present specification, and * is a bonding site with neighboring atoms.

M1 in Formula 1 may be selected from an integer of 1 to 3. m1 represents the number of A 1 , and when m 1 is 2 or more, 2 or more A 1 s may be the same or different from each other.

For example, the A 1 may be selected from the group represented by the following formulas (1-1) and (1-2):

Figure pat00011

In the above formulas 1-1 (1) and 1-1 (2), R 11 and c 11 are the same as described in the specification, and * is a bonding site with neighboring atoms.

L 1 to L 3 , L 21 , L 31 and L 41 in the above formulas (1), (2A), (2B) and (2-1) independently represent a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted 2 non-condensed polycyclic aromatic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted 2 May be selected from substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic groups.

For example, L 1 to L 3 , L 21 , L 31 and L 41 may be, independently of each other,

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, An acenaphthyl group, an acenaphthyl 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, a fluoranthenyl group, a triphenylgrenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a phenenyl group, a perylrrylanyl group, a pentaphenyl group, a hexacenyl group, A naphthyl group, a cyanyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, A thiazolyl group, an isothiazolyl group, an indolyl group, an indazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, A quinolinyl group, a quinolinyl group, a carbazolyl group, a phenanthridinyl group, an aralkoxy group, an acenaphthyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, an oxadiazolyl group, A benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a oxazolyl group, an oxazolyl group, an oxazolyl group, Substituted with at least one of a thiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group , A phenylene group, a pentalenylene group, A phenylene group, a neopentylene group, a neopentylene group, a neopentylene group, a naphthylene group, an azulenylene group, a heptarenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spioro-fluorenylene group, , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylrenylene group, A thiophenylene group, a thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, a thiophenylene group, a thiophenylene group, An isoindolylene group, an indolylene group, an indazololylene group, a prolinylene group, a quinolinylene group, an isoindolylene group, an isothiophenylene group, an isoindolylene group, An isoquinolinylene group, a benzoquinolinylene group, A phenanthrenylene group, a phenanthrolinylene group, a phenanthrene group, a benzoimide group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, A thiadiazole group, a thiadiazole group, an imidazopyridinylene group, and an imidazopyrimidinylene group; ≪ / RTI >

As another example, each of L 1 to L 3 , L 21 , L 31 and L 41 may independently be selected from the group represented by the following formulas (3-1) to (3-41)

Figure pat00012

Figure pat00013

Figure pat00014

Figure pat00015

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 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group A quinazolinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and -Si (Q 33 ) (Q 34 ) (Q 35 )

Q 33 to Q 35 are independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,

d2 is 1 or 2,

d3 is selected from integers from 1 to 3,

d4 is selected from integers from 1 to 4,

d5 is selected from an integer of 1 to 5,

d6 is selected from integers from 1 to 6,

d8 is selected from integers from 1 to 8,

* And * are binding sites with neighboring atoms.

According to one embodiment, L 1 to L 3 , L 21 , L 31 and L 41 may be independently selected from the group consisting of the following formulas (4-1) to (4-35)

Figure pat00016
Figure pat00017
Figure pat00018

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

A1 to a3, a21, a31 and a41 in the general formulas (1), (2A) and (2B) may be independently selected from integers of 0 to 3. a1 represents the number of L 1 in the formula (1), and when a1 is 2 or more, 2 or more L 1 may be the same or different from each other. When a1 is 0, * - (L 1 ) a1 - * 'becomes a single bond. a2, a3, a21, a31 and a41 can be understood with reference to the description of a1 and the structures of the above formulas 1, 2A and 2B.

According to one embodiment, a1 to a3, a21 and a41 are independently 0 or 1, and a31 is an integer of 1 to 3.

Ar 21 , Ar 41 and Ar 42 in the above formulas (2A), (2B) and (2-1) 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 1 - C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, Ar 21 , Ar 41 and Ar 42 may be, independently of each other,

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klycenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, An isothiazolyl 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, an indolyl group, an indazolyl group , A pyridyl group, a pyranyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinolinyl group, a carbazolyl group, A benzothiazolyl 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, An imidazopyrimidinyl group, and a -Si (Q 31 ) (Q 32 ) group, a thiazolyl group, an oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, (Q 33 ), a phenyl group, a biphenyl group, a terphenyl group, a pen An acenaphthyl group, an acenaphthyl 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, 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 pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl 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, Quinoxalinyl group, quinazolinyl group, cyano group, carbazolyl group, phenan A benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an isobenzoxazolyl group, an isobenzothiazolyl group, an isoxazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; ≪ / RTI >

Q 31 to Q 33 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro- A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolyl group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group.

As another example, Ar 21 , Ar 41 and Ar 42 may be independently selected from the group represented by the following formulas (5-1) to (5-79)

Figure pat00019

Figure pat00020

Figure pat00021

Figure pat00022

Figure pat00023

Figure pat00024
Figure pat00025
Figure pat00026

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

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

Z 31 to Z 37 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group A quinazolinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and -Si (Q 33 ) (Q 34 ) (Q 35 )

Q 33 to Q 35 are independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group,

e2 is 1 or 2,

e3 is selected from integers from 1 to 3,

e4 is selected from integers from 1 to 4,

e5 is selected from integers from 1 to 5,

e6 is selected from integers from 1 to 6,

e8 is selected from integers from 1 to 8,

* Is a binding site with neighboring atoms.

According to one embodiment, Ar 21 , Ar 41 and Ar 42 may be independently selected from the group consisting of the following formulas (6-1) to (6-44):

Figure pat00027
Figure pat00028
Figure pat00029
Figure pat00030

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

R 1 to R 3 , R 11 to R 18 and R 21 to R 50 in the general formulas (1), (2) and (2B) independently of one another are a group represented by the general formula (2-1), hydrogen, deuterium, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, A substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, An unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, and -Si (Q 1 ) (Q 2 ) (Q 3 ).

According to one embodiment, R 1 to R 3 , R 11 to R 18 and R 21 to R 50 are, independently of each other,

A group represented by Formula 2-1, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group;

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, , A pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group, Of the oxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, imidazo pyrimidinyl group and a -Si (Q 31) (Q 32 ) (Q 33) A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl 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 pyrazinyl group, a pyrazinyl group, a pyrrolyl group, a thiophenyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A benzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, Saadi azole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl 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 another embodiment, R 1 to R 3 , R 11 to R 18 and R 21 to R 50 , independently of each other,

A group represented by Formula 2-1, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, (Q) (Q 31 ) (Q 31 ), or a salt thereof, or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, 32 ) and (Q 33 ), each of which is substituted with at least one of a hydrogen atom, a fluorine atom, a fluorine atom, and a fluorine atom; 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.

In the above formulas (1) and (1-1), c1 and c2 are independently selected from integers of 0 to 4, and c11 may be selected from integers of 0 to 7. c1 represents the number of R 1 in the formula (1). When c1 is 2 or more, two or more R 1 may be the same or different. c2 and c11 can be understood with reference to the description of c1 and the structures of the above formulas (1) and (1-1).

According to one embodiment, c1, c2 and c11, independently of one another, can be 0 or 1.

X 21 , X 31 and X 32 in the above formulas (2A) and (2B) may be independently of each other O or S. For example, X 31 and X 32 may be the same as each other.

According to one embodiment, the first compound may be represented by the formula (1A): < EMI ID =

≪

Figure pat00031

The description of A 1 , m 1 , L 1 , a 1 , R 1 , R 2 , c 1 and c 2 in the above formula (1A) is as described in the present specification.

According to another embodiment, the first compound may be represented by the following formula (1A-1) or (1A-2):

≪ Formula 1A-1 &

Figure pat00032

≪ Formula 1A-2 >

Figure pat00033

The description of L 1 , a 1 , R 1 , R 2 , R 11 , c 1, c 2 and c 11 in the above formulas 1A-1 and 1A-2 is as described in the present specification.

For example, L 1 is selected from the groups represented by the above formulas (3-1) to (3-41) (for example, the groups represented by the above formulas (4-1) to (4-35)

a1 is 0 or 1,

R 1 , R 2 and R 11 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, A salt, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, (Q) (Q 31 ) (Q 31 ), or a salt thereof, or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, 32 ) and (Q 33 ), each of which is substituted with at least one of a hydrogen atom, a fluorine atom, a fluorine atom, and a fluorine atom; 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.

N1 of the formula (1) - - as shown to the number of - [(L 1) a1 ( A 1) m1], may be selected from an integer from 1 to 3. For example, n1 may be 1 or 2. when n1 is 2 or more than 2 * - [(L 1) a1 - (A 1) m1] may be the same or different from each other.

N2 in the formula ( 1 ) represents the number of * - [(L 2 ) a 2 - (R 1 ) c 1 ], and may be selected from an integer of 0 to 8. For example, n2 can be 0, 1 or 2. When n2 is 2 or more, 2 or more * - [(L 2 ) a 2 - (R 1 ) c 1 ] may be the same or different from each other.

N3 in the formula (1) represents the number of * - [(L 3 ) a 3 - (R 2 ) c 2 ], and may be selected from an integer of 0 to 7. For example, n3 can be 0, 1, or 2. When n3 is 2 or more, 2 or more * - [(L 3 ) a 3 - (R 2 ) c 2 ] may be the same or different from each other.

According to one embodiment, the second compound may be represented by one of the following formulas 2A-1, 2A-2 or 2B-1:

≪ Formula 2A-1 >

Figure pat00034

≪ Formula 2A-2 >

Figure pat00035

≪ Formula (2B-1) >

Figure pat00036

The description of X 21 , X 31 , X 32 , L 21 , L 31 , a 31 and Ar 21 in the above Chemical Formulas 2A-1, 2A-2 and 2B-1 refers to those described in this specification.

For example, X 21 , X 31 and X 32 are independently of each other O or S,

L 21 and L 31 are independently selected from the groups represented by the above formulas 3-1 to 3-41 (for example, the groups represented by the above formulas 4-1 to 4-35)

a31 is selected from integers from 1 to 3,

Ar 21 is selected from the group represented by the above formulas 5-1 to 5-79 (for example, the group represented by the above formulas 6-1 to 6-44)

R 23 may be selected from the group represented by the formula (2-1).

The first compound is one of the following compounds A1 to A18, and the second compound is one of the following compounds B1 to B17, but is not limited thereto:

Figure pat00037

Figure pat00038

Figure pat00039

Figure pat00040

When the first compound and the second compound are included in the light emitting layer, the synergistic effect of the first compound and the second compound reduces the electric or electronic stress generated in the light emitting layer when the organic light emitting device is driven. And the electron-hole balance is improved, so that the high efficiency and long life of the organic light emitting device can be achieved at the same time.

The first compound has an excellent hole transporting efficiency due to the bonding of a naphthyl group as a hole transporting moiety to an anthracene core and the second compound has a diarylamino group in a molecule and thus has an excellent electron transport efficiency. And when the second compound is co-deposited as a light emitting layer host, the balance of hole transport and electron transport is excellent, thereby achieving high efficiency and long life effect of the organic light emitting device.

Both the first compound and the second compound may be included in the light emitting layer of the organic layer 150. Alternatively, the first compound may be included in the light emitting layer in the organic layer 150, and the second compound may be included in the electron transporting region between the light emitting layer and the second electrode. As another example, both the first compound and the second compound are included in the light emitting layer in the organic layer 150, and the second compound may be included in the electron transporting region between the light emitting layer and the second electrode. At this time, the second compound contained in the light emitting layer and the second compound contained in the electron transporting region may be the same or different.

When both the first compound and the second compound are included in the light emitting layer, the bonding region of holes and electrons can be moved to the interface side between the light emitting layer and the electron transporting region, thereby contributing to an improvement in the lifetime of the organic light emitting device.

The weight ratio of the first compound to the second compound may be selected within the range of 10:90 to 90:10. For example, the weight ratio of the first compound to the second compound may be selected within the range of 20:80 to 75:25. When the weight ratio of the first compound and the second compound is in the range described above, it is possible to effectively balance hole transport and electron transport in the light emitting layer.

The organic layer 150 may include a hole transporting region interposed between the first electrode and the light emitting layer, and an electron transporting region interposed between the light emitting layer and the second electrode.

The holes injected from the first electrode 110 are injected into the light emitting layer through the hole transport region.

The hole transporting region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layered structure having a plurality of layers made of a plurality of different materials.

The hole transporting region 130 includes a hole injection layer / hole transporting layer, a hole injecting layer / a hole transporting layer / a hole transporting layer, a hole transporting layer / a hole transporting layer / a buffer layer / But are not limited to, a structure of an injection layer / hole assist layer, hole injecting layer / buffer layer / hole assist layer, hole transport layer / hole assist layer and hole transport layer / buffer layer / hole assist layer. Alternatively, the hole transporting region 130 may include only a hole injecting layer, or may include only a hole transporting layer.

When the hole transporting region includes a hole injection layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 by using various methods.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may include, for example, a deposition temperature of about 100 to about 500 DEG C, a vacuum degree of about 10 -8 to about 10-3 torr, and a deposition rate of about 0.01 to about 100 A / sec The hole injection layer structure to be formed and the hole injection layer structure to be formed within the deposition rate range of the hole injection layer to be formed.

When the hole injection layer is formed by the spin coating method, the coating conditions include a compound for a hole injection layer to be deposited and a hole for formation to be formed within a range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature range of about 80 [ Can be selected in consideration of the injection layer structure.

When the hole transporting region includes a hole transporting layer, the hole transporting layer may be formed by a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging The hole transport layer may be formed on the first electrode 110 or on the hole injection layer using various methods. When the hole transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the hole transport layer refer to the deposition conditions and the coating conditions of the hole injection layer.

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

Figure pat00041

Figure pat00042

≪ Formula 201 >

Figure pat00043

≪ EMI ID =

Figure pat00044

Of the above formulas (201) and (202)

The descriptions for L 201 to L 205 are independent of each other, see the description of L 1 in this specification;

xa1 to xa4 are independently selected from 0, 1, 2 and 3;

xa5 is selected from 1, 2, 3, 4 and 5;

R 201 to R 204 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 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent ring non-fused polycyclic aromatic group, and a substituted or unsubstituted monovalent ring non-aromatic heterocyclic group condensed polycyclic ≪ / RTI >

For example, of the above formulas (201) and (202)

L 201 to L 205 independently from each other,

A phenylene group, a phenanthrene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinyl group, a pyrenyl group, a pyrenyl group, A phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, 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 A pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxaline group, a quinolyl group, A naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenyl group, a dibenzofluorenyl group, a dibenzofluorenyl group, a dibenzofluorenyl group, a dibenzofluorenyl group, A phenanthrenylene group, an anthracenylene group, a pyrenylene group, Group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a group pyridazinyl, quinolinyl group, isoquinolinyl group, quinoxalinyl carbonyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; ≪ / RTI >

xa1 to xa4 are, independently of each other, 0, 1 or 2;

xa < 5 > is 1, 2 or 3;

R 201 to R 204 independently from each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, A pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, A phenylene group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, A decyl group, a decyl group, a decyl group, a decyl group, a decyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; , But is not limited thereto.

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

≪ Formula 201A >

Figure pat00045

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>

Figure pat00046

The compound represented by the formula (202) may be represented by the following formula (202A), but is not limited thereto:

&Lt; Formula 202A >

Figure pat00047

Description of the Formula 201A, 201A-1 and 202A of the L 201 to L 203, xa1 to xa3, xa5 and R 202 to R 204, see what described in the specification and description of the R 211 and R 212 is R 203 R 213 to R 216 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkyl group, C 1 -C 6 alkenyl group, alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 - C 60 aryl group giok, C 6 -C 60 aryl giti import, C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic fused polycyclic group may be selected from have.

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

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

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. When the hole transporting region includes both the hole injecting layer and the hole transporting layer, the thickness of the hole injecting layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å For example, from about 100 A to about 1500 A, for example. 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.

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

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And the following compound HT-D1, but the present invention is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

Figure pat00052
Figure pat00053

The hole transporting region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injecting layer and the hole transporting layer as described above. The buffer layer may compensate the optical resonance distance according to the wavelength of the light emitted from the light emitting layer to increase the light emission efficiency. As the material contained in the buffer layer, a material that can be included in the hole transporting region may be used. The electron blocking layer is a layer that prevents the injection of electrons from the electron transporting region.

A vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, or the like is performed on the first electrode 110 or the hole transporting region. ) And the like are used to form a light emitting layer. When the light emitting layer is formed by the vacuum deposition method and the spin coating method, the deposition condition and the coating condition of the light emitting layer refer to the deposition condition and the coating condition of the hole injection layer.

When the organic light emitting device 10 is a full color organic light emitting device, it may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each light emitting layer and individual sub-pixels. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are laminated or a structure in which a red light emitting material, a green light emitting material and a blue light emitting material are mixed without layering, and emits white light.

The light emitting layer may include a host and a dopant. The host may comprise the first compound and the second compound. For a description of the first compound and the second compound, reference is made to what is described herein.

The dopant may comprise a phosphorescent dopant or a fluorescent dopant.

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

&Lt; Formula 401 >

Figure pat00054

In the above formula (401)

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

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

The A 401 and A 402 rings may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted indene Substituted or unsubstituted thiophenes, substituted or unsubstituted thiophenes, substituted or unsubstituted furan, substituted or unsubstituted imidazoles, substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, Substituted or unsubstituted thiazoles, substituted or unsubstituted isothiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted isoxazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrazines, substituted or unsubstituted pyrimidines, Substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, Substituted or unsubstituted benzoimidazoles, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophenes, substituted or unsubstituted isobenzothiophenes, substituted or unsubstituted benzothiophenes, substituted or unsubstituted benzothiophenes, Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, And substituted or unsubstituted dibenzothiophene;

The substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, Substituted thiazoles, substituted thiazoles, substituted isothiazoles, substituted oxazoles, substituted isoxazoles, substituted pyridines, substituted pyrazines, substituted pyrimidines, substituted pyridazines, substituted quinolines, substituted isoquinolines, Substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of the benzooxazole, the substituted triazole, the substituted oxadiazole, the substituted triazine, the substituted dibenzofuran and the substituted dibenzothiophene,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy groups (aryloxy), C 6 -C 60 arylthio group (arylthio), C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group (non-condensed polycyclic aromatic group), a 1 non-aromatic heterocyclic condensed polycyclic group, -N (Q 401) (Q 402), -Si (Q 403) (Q 404) (Q 405) and -B (Q 406) substituted with at least one of (Q 407), 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 hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryl giok group, 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, -N (Q 411) (Q 412), -Si (Q 413) (Q 414) (Q 415) A C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkyl group substituted with at least one of -B (Q 416 ) (Q 417 ) alkenyl 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, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

Q 421 , Q 422 , Q 423 , Q 424 , Q 425 , and -B Q 426 , Q 427 ; ;

L 401 is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3,

The Q 401 to Q 407, Q 411 to Q 417, and Q 421 to Q 427 are independently, hydrogen, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 6 -C 60 aryl group and C 2 - C 60 heteroaryl is selected from an aryl group.

The L 401 may be any monovalent, divalent or trivalent organic ligand. For example, L 401 may be a halogen ligand (e.g. Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-l, 3- propanedionate, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g., picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon But are not limited to, monooxide ligands, isonitrile ligands, cyano ligands, and phosphorus ligands (e.g., phosphine, phosphite).

If the formula of A 401 401 is to have two or more substituents, bonded to each other at least two substituents of A 401 can form a saturated or unsaturated ring.

If the formula of A 401 402 is to have two or more substituents, bonded to each other at least two substituents of A 402 can form a saturated or unsaturated ring.

When xc1 in Formula 401 is 2 or more, a plurality of ligands of Formula 401

Figure pat00055
May be the same or different from each other. If the formula xc1 401 is 2 or more of, A 401 and A 402 are each of the other ligands neighboring A and 401 respectively direct and A 402 (directly) or linking group (e.g., C 1 -C 5 alkylene group, -N (R ') - (wherein, R' - may be connected across a) is C 1 -C 10 alkyl or C 6 -C 20 aryl group), or -C (= O).

The phosphorescent dopant may, for example, be selected from among the following compounds PD1 to PD75, but is not limited thereto:

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

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

<Formula 501>

Figure pat00069

In the above formula (501)

Ar 501

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 - C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic -Si (Q 501) (Q 502 ) (Q 503) ( Q 501 to Q 503 are the independently from each other , Naphthalene, heptarene, flu, substituted with at least one selected from hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 6 -C 60 aryl group and a C 1 -C 60 heteroaryl group. Ore, spiro-fluorene, Division fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, pisen, perylene, penta pen and indeno anthracene; &Lt; / RTI &gt;

The descriptions of L 501 to L 503 refer to the description of L 1 in the present specification, respectively;

R 501 and R 502 , independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, 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 Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofuranyl group substituted with at least one member selected from the group consisting of a benzyl group, A dibenzofluorenyl group, a phenanthrenyl group, an A pyridinyl 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, Triazinyl group, dibenzofuranyl group and dibenzothiophenyl group; ;

xd1 to xd3 are independently selected from 0, 1, 2 and 3;

xd4 is selected from 1, 2, 3 and 4.

The fluorescent dopant may comprise at least one of the following compounds FD1 to FD9:

Figure pat00070

Figure pat00071

Figure pat00072

Figure pat00073

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. According to one embodiment, the thickness of the light emitting layer may range from about 100 A to about 250 A. 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.

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

Figure pat00074

Figure pat00075

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.

Next, an electron transporting region may be disposed above the light emitting layer.

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

For example, the electron transporting region may have a structure of an electron transporting layer / electron injecting layer or a hole blocking layer / electron transporting layer / electron injecting layer stacked sequentially from the light emitting layer, but the present invention is not limited thereto.

According to one embodiment, the organic layer 150 of the organic light emitting device may include an electron transporting region interposed between the light emitting layer and the second electrode 190.

When the electron transporting region includes a hole blocking layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole blocking layer may be formed on the light emitting layer. When the hole blocking layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the hole blocking layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

Figure pat00076

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

The electron transporting region may include an electron transporting layer. The electron transport layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) And may be formed on the light emitting layer or on the hole blocking layer. When the electron transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron transport layer refer to the deposition conditions and coating conditions of the hole injection layer.

Meanwhile, the electron transport layer may include at least one of a compound represented by the following formula (601) and a compound represented by the following formula (602).

<Formula 601>

Ar 601 - [(L 601 ) xe 1 -E 601 ] xe 2

In the above formula (601)

Ar 601

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 - C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic -Si (Q 301) (Q 302 ) (Q 303) ( Q 301 to Q 303 are the independently from each other Heptarenylene, fluorene, substituted naphthalene, heptylene, fluorene, substituted heptylene, heptylene, fluorene, and the like, substituted with at least one selected from hydrogen, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 6 -C 60 aryl or C 1 -C 60 heteroaryl. Spiro-fluorene, benzofluor Phenanthrene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, klysene, naphthacene, picene, perylene, pentaphene and indenoanthracene; ;

For a description of L 601 , see the discussion of L 201 herein;

E 601 ,

A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, isoxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, pyridazinyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl 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 phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group (ben and examples thereof include benzofuranyl, benzofuranyl, benzofuranyl, benzofuranyl, zofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, An oxadiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, A pyrimidinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 1 -C 20 alkyl, C 1 -C 20 alkoxy group, 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 naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, A naphthacenyl group, a phenanthryl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyridinyl 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 naphthyl group, A phenanthrolinyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an isothiazolyl group, Benzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzoyl group A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , Isoxazole diol, pyridinyl 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 naphthyridyl group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzothiophenyl group, a benzothiophenyl group, an isobenzyl group, a benzothiophenyl group, an isothiazolyl group, A thiazolyl group, a thiazolyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbamoyl group, a benzoxazolyl group, A pyrrolyl group, an imidazopyridinyl group and an imidazolopyrimidinyl group; ;

xe1 is selected from 0, 1, 2 and 3;

xe2 is selected from 1, 2, 3 and 4.

<Formula 602>

Figure pat00077

In the above formula (602)

611 X is N or C- (L 611) xe611 -R 611 , X 612 is N or C- (L 612) xe612 -R 612 , X 613 is N or C- (L 613) xe613 -R 613, and , At least one of X 611 to X 613 is N;

The descriptions of L 611 to L 616 each refer to the description of L 1 in this specification;

R 611 to R 616 , independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 1 -C 20 alkyl, C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spy-fluorenyl group, benzo fluorenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalyl group, A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorene group substituted with at least one of a hydrogen atom, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group , A pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazole group possess; ;

xe611 to xe616 are independently selected from 0, 1, 2 and 3;

The compound represented by Formula 601 and the compound represented by Formula 602 may be independently selected from the following compounds ET1 to ET15:

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Alternatively, the electron transport layer may include at least one of the BCP, Bphen and to Alq 3, Balq, TAZ and NTAZ.

Figure pat00083

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

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.

Figure pat00084

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190.

The electron injecting layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) , And on the electron transport layer. When the electron injection layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron injection layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li 2 O, BaO and LiQ.

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.

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. At this time, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, Can be used. Specific examples of the material for the second electrode 190 include Li, Mg, Al, Al-Li, Ca, Mg-In, , Magnesium-silver (Mg-Ag), and the like. Alternatively, ITO or IZO may be used as the material for the second electrode 190. The second electrode 190 may be a transflective electrode or a transmissive electrode.

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

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.

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 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 ethynyl, propynyl, and the like. 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.

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 , And specific examples thereof include 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 aromatics, Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C 3 -C 10 cycloalkenylene group means a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.

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

In the present specification, a C 6 -C 60 aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C 6 -C 60 arylene group means a carbamoyl group having 6 to 60 carbon atoms Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl 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 carbocyclic aromatic system having from 1 to 60 carbon atoms C 1 -C 60 heteroarylene group means a divalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms . 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 fused together.

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 monovalent aromatic 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 non-aromatic. (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 condensed heteropolycyclic group in which two or more rings are condensed with each other and a heteroatom selected from N, O, Si, P and S in addition to carbon as a ring- (For example, having from 1 to 60 carbon atoms) having a non-aromatic group as a whole. The monovalent non-aromatic heterocyclic polycyclic group includes 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 substituted condensed polycyclic group, 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 heterocycloalkyl alkenylene group, substituted C 6 -C 60 aryl group, a substituted C 1 -C 60 heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic heterocyclic 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 60 alkoxy group, a substituted C 3 -C 10 Substituted cycloalkyl groups, substituted C 1 -C 10 heterocycloalkyl groups, substituted C 3 -C 10 cycloalkenyl groups, substituted C 1 -C 10 heterocycloalkenyl groups, substituted C 6 -C 60 aryl groups, 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 a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic Sum at least one of the substituent of the polycyclic group,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy groups (aryloxy), C 6 -C 60 arylthio group (arylthio), C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q 11) (Q 12 ), -Si (Q 13) (Q 14) (Q 15) and -B (Q 16) (Q 17 ) at least one substituted, C 1 -C 60 alkyl, C of 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 hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 - C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q 21) (Q 22), -Si (Q 23) (Q 24) (Q 25) and -B (Q 26) (Q 27 ) of the at least one substituted, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkyl alkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 -C 60 H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

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

Wherein Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 and Q 37 to Q 37 are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or its salt, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl A C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

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

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]

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 4,4'-bis [N- (1-naphthyl) -N-phenylamino] Phenyl (hereinafter referred to as NPB) was vacuum-deposited to form a hole transporting layer having a thickness of 300 ANGSTROM.

Compound A3 (first host), compound B2 (second host), and PD1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 70:20:10 to form a 400Å thick light emitting layer.

Alq 3 was vacuum deposited on the light emitting layer to form an electron transporting layer having a thickness of 300 A, and LiF was deposited on the electron transporting layer to form an electron transporting region having a thickness of 10 A to form an electron transporting region.

Al was vacuum-deposited on the electron transporting region to form a cathode having a thickness of 2000 A to prepare an organic light emitting device.

Figure pat00085

Example 2

Except that Compound A3 (first host), Compound B2 (second host), and PD1 (dopant) were co-deposited at a weight ratio of 60:30:10 during the formation of the light emitting layer, To prepare an organic light emitting device.

Example 3

That the compound B3 was used instead of the compound B2 as the second host in the formation of the light emitting layer and the compound A3 (the first host), the compound B13 (the second host) and the PD1 (dopant) were coprecipitated at a weight ratio of 75:15:10 , An organic light emitting device was fabricated using the same method as in Example 1 above.

Example 4

That the compound B3 was used instead of the compound B2 as the second host in the formation of the light emitting layer and the compound A3 (the first host), the compound B13 (the second host) and the PD1 (dopant) were coprecipitated at a weight ratio of 65:25:10 , An organic light emitting device was fabricated using the same method as in Example 1 above.

Example 5

That Compound A8 (first host), Compound B2 (second host) and PD1 (dopant) were co-deposited at a weight ratio of 30:60:10, using Compound A8 instead of Compound A3 as the first host in forming the light emitting layer , An organic light emitting device was fabricated using the same method as in Example 1 above.

Example 6

Compound A8 (first host), compound B2 (second host), and PD1 (dopant) were co-deposited at a weight ratio of 20:70:10 using Compound A8 instead of Compound A3 as the first host in the formation of the light emitting layer , An organic light emitting device was fabricated using the same method as in Example 1 above.

Example 7

Compound A8 (first host), compound B13 (second host) and PD1 (dopant) were used in place of compound A3 as a first host and Compound B13 was used in place of compound B2 as a second host. The organic light emitting device was fabricated in the same manner as in Example 1 except that co-deposition was performed at a weight ratio of 30:60:10.

Example 8

Compound A8 (first host), compound B13 (second host) and PD1 (dopant) were used in place of compound A3 as a first host and Compound B13 was used in place of compound B2 as a second host. The organic light emitting device was fabricated in the same manner as in Example 1 except that co-deposition was performed at a weight ratio of 20:70:10.

Comparative Example 1

Except that the compound B2 was not used as the second host in forming the light emitting layer and the compound A3 (first host) and PD1 (dopant) were co-deposited at a weight ratio of 90:10, To prepare an organic light emitting device.

Comparative Example 2

Compound A8 (first host) and PD1 (dopant) were co-deposited at a weight ratio of 90:10 without using Compound A8 as the first host and Compound B2 as the second host in the formation of the light emitting layer , An organic light emitting device was fabricated using the same method as in Example 1 above.

Comparative Example 3

Except that Compound A3 was not used as the first host in forming the light emitting layer and the compound B2 (second host) and PD1 (dopant) were co-deposited at a weight ratio of 90:10, To prepare an organic light emitting device.

Comparative Example 4

Compound B13 was used instead of Compound B2 as the second host and Compound B13 (second host) and PD1 (dopant) were co-deposited at a weight ratio of 90:10 without using Compound A3 as the first host in the light emitting layer formation , An organic light emitting device was fabricated using the same method as in Example 1 above.

.

Comparative Example 5

An organic luminescent device was manufactured using the same method as in Example 1, except that Compound C was used instead of Compound A3 as the first host and Compound D was used in place of Compound B2 as the second host in forming the light emitting layer Respectively.

Figure pat00086

Evaluation example 1

The efficiency and lifetime (T 95 ) of the organic light emitting device fabricated in Examples 1 to 8 and Comparative Examples 1 to 5 were measured using Kethley SMU 236 and luminance meter PR650, and the results are shown in Table 1. The lifetime T 95 is the time taken for the luminance to become 95% of the initial luminance after driving the organic light emitting element.

The light- efficiency
(cd / A)
Lifetime (T 95 )
(9000 nit)
The first host Second host Dopant Weight ratio Example 1 Compound A3 Compound B2 PD1 70:20:10 30.8 108 Example 2 Compound A3 Compound B2 PD1 60:30:10 24.9 101 Example 3 Compound A3 Compound B13 PD1 75:15:10 44.8 110 Example 4 Compound A3 Compound B13 PD1 65:25:10 42.7 127 Example 5 Compound A8 Compound B2 PD1 30:60:10 38.4 84 Example 6 Compound A8 Compound B2 PD1 20:70:10 25.7 88 Example 7 Compound A8 Compound B13 PD1 30:60:10 40.2 82 Example 8 Compound A8 Compound B13 PD1 20:70:10 38.7 114 Comparative Example 1 Compound A3 - PD1 90:10 14.7 49 Comparative Example 2 Compound A8 - PD1 90:10 10.8 58 Comparative Example 3 - Compound B2 PD1 90:10 11.6 58 Comparative Example 4 - Compound B13 PD1 90:10 12.1 67 Comparative Example 5 Compound C Compound D PD1 70:20:10 18.2 64

Figure pat00087

It can be seen from Table 1 that the organic light emitting devices of Examples 1 to 8 have higher efficiency and longer life than the organic light emitting devices of Comparative Examples 1 to 5.

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

Claims (10)

A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer,
Wherein the organic layer comprises a first compound and a second compound,
Wherein the first compound is selected from compounds represented by the following general formula (1)
Wherein the second compound is selected from compounds represented by the following Chemical Formulas 2A and 2B:
&Lt; Formula 1 >
Figure pat00088

&Lt; Formula 1-1 >
Figure pat00089

&Lt; Formula 2A >
Figure pat00090

(2B)
Figure pat00091

&Lt; Formula (2-1)
Figure pat00092

Among the above Chemical Formulas 1, 1-1, 2A, 2B and 2-1,
A 1 is selected from the group represented by the formula (1-1)
m1 is selected from integers from 1 to 3,
X 21 , X 31 and X 32 are independently of each other O or S,
L 1 to L 3 , L 21 , L 31 and L 41 independently represent a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, 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 1 - C 60 heteroaryl group, an unsubstituted 2-substituted or unsubstituted non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non-aromatic hydrocarbon ring condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a1 to a3, a21, a31 and a41 are each independently selected from an integer of 0 to 3,
Ar 21 , Ar 41 and Ar 42 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 A substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted aryl group, Aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups,
R 1 to R 3 , R 11 and R 21 to R 50 independently of one another are a group represented by the above formula (2-1), hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C 1 -C 60 alkyl group, A substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted Or a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 10 heterocycloalkyl group, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic group and the condensed polycyclic -Si (Q 1) (Q 2 ) (Q 3 ), &Lt; / RTI &gt;
c1 and c2 are each independently selected from an integer of 0 to 4,
c11 is selected from an integer of 0 to 7,
n1 is selected from integers from 1 to 3, n2 is selected from integers from 0 to 8, n3 is selected from integers from 0 to 7,
At least one of R 21 to R 30 is selected from the group represented by the above formula (2-1)
* Is the binding site with neighboring atoms,
The substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted a C 6 -C 60 aryl group, a substituted C 1 -C 60 heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C 1 -C 60 A substituted C 2 -C 60 alkenyl group, a substituted C 2 -C 60 alkynyl group, a substituted C 1 -C 60 alkoxy group, a substituted C 3 -C 10 cycloalkyl group, a substituted C 1 -C 10 hetero A substituted C 3 -C 10 cycloalkenyl group, a substituted C 1 -C 10 heterocycloalkenyl group, a substituted C 6 -C 60 aryl group, a substituted C 6 -C 60 aryloxy group, a substituted C 6 -C 60 arylthio group, a substituted C 1 -C 60 heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic hydrocarbon ring condensed at least one substituent of the polycyclic group,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy groups (aryloxy), C 6 -C 60 arylthio group (arylthio), 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) and -N (Q 14) (Q 15 ) of the at least one substituted, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, 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 hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocyclo alkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 - C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -Si (Q 21) (Q 22) (Q 23) and -N (Q 24) (Q 25 ) C 1 -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 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, 1 Aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And
-Si (Q 31) (Q 32 ) (Q 33) and -N (Q 34) (Q 35 ); ;
Wherein Q 1 to Q 3 , Q 11 to Q 15 , Q 21 to Q 25 and Q 31 to Q 35 are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or its salt, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl A C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.
The method according to claim 1,
L 1 to L 3 , L 21 , L 31 and L 41 are, independently of each other,
A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , Anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, and the like. , Perylene, perylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, obarenylguanene, Ovalenylene, pyrrolylene, isoindolinone, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, thiophenylene, thiophenylene, isoxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, isoindolylene, isoindolylene, And examples thereof include indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinyl, And examples thereof include phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, phenanthridinylene, ), Acridinylene group (acr and isocyanates such as isobenzothiazolylene, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, isobenzothiazolyl, Benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzoyl, and the like. A dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazoylene group, an imidazopyridinylene group and an imidazopyrimidinylene group; And
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, An acenaphthyl group, an acenaphthyl 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, a fluoranthenyl group, a triphenylgrenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a phenenyl group, a perylrrylanyl group, a pentaphenyl group, a hexacenyl group, A naphthyl group, a cyanyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, A thiazolyl group, an isothiazolyl group, an indolyl group, an indazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, A quinolinyl group, a quinolinyl group, a carbazolyl group, a phenanthridinyl group, an aralkoxy group, an acenaphthyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, an oxadiazolyl group, A benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a oxazolyl group, an oxazolyl group, an oxazolyl group, Substituted with at least one of a thiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group , A phenylene group, a pentalenylene group, A phenylene group, a neopentylene group, a neopentylene group, a neopentylene group, a naphthylene group, an azulenylene group, a heptarenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spioro-fluorenylene group, , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylrenylene group, A thiophenylene group, a thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, a thiophenylene group, a thiophenylene group, An isoindolylene group, an indolylene group, an indazololylene group, a prolinylene group, a quinolinylene group, an isoindolylene group, an isothiophenylene group, an isoindolylene group, An isoquinolinylene group, a benzoquinolinylene group, A phenanthrenylene group, a phenanthrolinylene group, a phenanthrene group, a benzoimide group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, A thiadiazole group, a thiadiazole group, an imidazopyridinylene group, and an imidazopyrimidinylene group; &Lt; / RTI &gt;
The method according to claim 1,
Wherein L 1 to L 3 , L 21 , L 31 and L 41 are independently selected from the group consisting of the following formulas (4-1) to (4-35)
Figure pat00093
Figure pat00094
Figure pat00095

In the above formulas (4-1) to (4-35), * and * are binding sites with neighboring atoms.
The method according to claim 1,
Ar 21 , Ar 41 and Ar 42 are, independently of each other,
A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, A phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, and the like. Pentacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrole group, and the like. Pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, thiazolyl, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoindolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridine group, Phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzothiophenyl, Benzothiazolyl, isobenzothiazolyl, benzoxazoyl, Benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzocarbazolyl, and the like. ), Dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and the like. And
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klycenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, An isothiazolyl 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, an indolyl group, an indazolyl group , A pyridyl group, a pyranyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinolinyl group, a carbazolyl group, A benzothiazolyl 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, An imidazopyrimidinyl group, and a -Si (Q 31 ) (Q 32 ) group, a thiazolyl group, an oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, (Q 33 ), a phenyl group, a biphenyl group, a terphenyl group, a pen An acenaphthyl group, an acenaphthyl 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, 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 pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl 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, Quinoxalinyl group, quinazolinyl group, cyano group, carbazolyl group, phenan A benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an isobenzoxazolyl group, an isobenzothiazolyl group, an isoxazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; &Lt; / RTI &gt;
Q 31 to Q 33 independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro- A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolyl group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.
The method according to claim 1,
Wherein Ar 21 , Ar 41 and Ar 42 are independently selected from the group consisting of the following formulas (6-1) to (6-44):
Figure pat00096
Figure pat00097
Figure pat00098
Figure pat00099

In the above formulas (6-1) to (6-44), * denotes a bonding site with neighboring atoms.
The method according to claim 1,
R 1 to R 3 , R 11 to R 18 and R 21 to R 50 independently of one another,
A group represented by Formula 2-1, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, (Q) (Q 31 ) (Q 31 ), or a salt thereof, or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, 32 ) and (Q 33 ), each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano 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 independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
The method according to claim 1,
Wherein the first compound is represented by the following general formula (1A-1) or (1A-2):
&Lt; Formula 1A-1 &
Figure pat00100

&Lt; Formula 1A-2 >
Figure pat00101

The description of L 1 , a 1 , R 1 , R 2 , R 11 , c 1, c 2 and c 11 in the above formulas (1A-1) and
The method according to claim 1,
Wherein the second compound is represented by one of the following Chemical Formulas 2A-1, 2A-2, or 2B-1:
&Lt; Formula 2A-1 >
Figure pat00102

&Lt; Formula 2A-2 >
Figure pat00103

&Lt; Formula (2B-1) >
Figure pat00104

The description of X 21 , X 31 , X 32 , L 21 , L 31 , a31 and Ar 21 in the above Formulas 2A-1, 2A-2 and 2B-1 is the same as described in claim 1.
The method according to claim 1,
The first compound is one of the following compounds A1 to A18,
Wherein the second compound is one of the following compounds B1 to B17:
Figure pat00105

Figure pat00106

Figure pat00107

Figure pat00108
The method according to claim 1,
Wherein the first compound and the second compound are included in the light emitting layer.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109553624A (en) * 2017-09-25 2019-04-02 北京鼎材科技有限公司 A kind of compound and its application in organic electroluminescence device
WO2020080416A1 (en) * 2018-10-16 2020-04-23 出光興産株式会社 Organic electroluminescence element and electronic device
WO2020080417A1 (en) * 2018-10-16 2020-04-23 出光興産株式会社 Organic electroluminescent element and electronic device
CN112898305A (en) * 2019-12-03 2021-06-04 乐金显示有限公司 Organic compound, organic light emitting diode comprising the same, and organic light emitting device comprising the same
US11522135B2 (en) 2018-09-21 2022-12-06 Samsung Display Co., Ltd. Organic electroluminescence device and manufacturing method of the same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109553624A (en) * 2017-09-25 2019-04-02 北京鼎材科技有限公司 A kind of compound and its application in organic electroluminescence device
US11522135B2 (en) 2018-09-21 2022-12-06 Samsung Display Co., Ltd. Organic electroluminescence device and manufacturing method of the same
WO2020080416A1 (en) * 2018-10-16 2020-04-23 出光興産株式会社 Organic electroluminescence element and electronic device
WO2020080417A1 (en) * 2018-10-16 2020-04-23 出光興産株式会社 Organic electroluminescent element and electronic device
CN112823434A (en) * 2018-10-16 2021-05-18 出光兴产株式会社 Organic electroluminescent element and electronic device
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US11482675B1 (en) 2018-10-16 2022-10-25 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and electronic apparatus
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