KR102035938B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic electroluminescent device including the same.

Description

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification relates to a compound and an organic electroluminescent device including the same. This specification claims the benefit of the filing date of Korean Patent Application No. 10-2017-0094688 filed with the Korea Intellectual Property Office on July 26, 2017, the entire contents of which are incorporated herein.

The electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as necessary. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of the material of the organic thin film is continuously required.

Korean Laid-Open Patent Publication 2000-0051826

The present specification provides a compound and an organic electroluminescent device including the same.

The present application provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L 2 is a direct bond; Or a substituted or unsubstituted arylene group,

R1 to R7 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group Ring heterocyclic group,

m is an integer from 0 to 4, when m is 2 or more, R1 is the same as or different from each other,

n is an integer from 0 to 6, when n is 2 or more, R2 is the same as or different from each other,

0≤m + n≤9

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

The compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve light efficiency, and improve device life characteristics by thermal stability of the compound.

1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer ( 9) and an example of the organic electroluminescent element in which the cathode 4 are sequentially stacked are shown.
3 is a mass spectrum of Compound 1 according to an exemplary embodiment of the present invention.
4 is a mass spectrum of Compound 9 according to an exemplary embodiment of the present invention.
5 is a mass spectrum of Compound 33 according to an exemplary embodiment of the present invention.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a compound represented by Chemical Formula 1.

Examples of substituents herein are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Alkenyl groups; An alkoxy group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

Etc., but is not limited thereto.

,

등이 있다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl Group, acridil group, hydroacridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazin Ginopyrazinyl group, isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzo Thiophenyl group, benzofuranyl group, dibenzofuranyl group; Benzosilol group; Dibenzosilol group; Phenanthrolinyl group, isooxazolyl group, thiadiazolyl group, phenothiazinyl group, phenooxazinyl group, and condensation structures thereof, and the like, but are not limited thereto. In addition, examples of heterocyclic groups include heterocyclic structures including a sulfonyl group, for example,

,

Etc.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In one embodiment of the present specification, at least one of the R3 to R7 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, at least one of the R3, R5 and R6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, at least one of the R3, R5 and R6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, and R4 and R7 are hydrogen.

In one embodiment of the present specification, at least one of the R3, R5 and R6 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, at least one of the R3, R5 and R6 is a phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with an aryl group or an alkyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with aryl groups; A benzocarbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, at least one of the R3, R5 and R6 is a phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a phenyl group or a methyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with a phenyl group; A benzocarbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, R3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, R3 is a phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with an aryl group or an alkyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with aryl groups; A benzocarbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R3 is a phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a phenyl group or a methyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with a phenyl group; A benzocarbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with an aryl group or an alkyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with aryl groups; A benzocarbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a phenyl group or a methyl group; Spirobifluorene group; Phenanthrene groups; Triphenylene group; Carbazole groups substituted or unsubstituted with a phenyl group; A benzocarbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R1 is hydrogen.

In one embodiment of the present specification, R2 is hydrogen or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, R2 is hydrogen or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, R2 is hydrogen or a dibenzothiophene group.

In one embodiment of the present specification, R1 and R2 are hydrogen.

In one embodiment of the present specification, R4 and R7 are hydrogen.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted triazine group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzothienopyrimidine group; Substituted or unsubstituted benzofurypyrimidine group; Or a substituted or unsubstituted benzoquinazolin group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Spirobifluorene group unsubstituted or substituted with an aryl group; A quinazoline group unsubstituted or substituted with an aryl group; Benzoquinazolin group unsubstituted or substituted by an aryl group; Triazine group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an aryl group; A benzocarbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group unsubstituted or substituted with an aryl group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Benzothienopyrimidine group unsubstituted or substituted by an aryl group; A benzopuropyrimidine group unsubstituted or substituted with an aryl group; Or a benzoquinazolin group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a phenyl group; Biphenyl group; Fluorene groups substituted with alkyl or aryl groups; Spirobifluorene group; A quinazoline group substituted with an aryl group; Benzoquinazolin group substituted by the aryl group; Triazine group unsubstituted or substituted with an aryl group; Carbazole groups unsubstituted or substituted with an aryl group; A benzocarbazole group unsubstituted or substituted with an aryl group; Dibenzofuran group; Dibenzothiophene group; Benzothienopyrimidine group substituted by the aryl group; Benzopuropyrimidine groups substituted with aryl groups; Or a benzoquinazolin group substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a phenyl group; Biphenyl group; A fluorene group substituted with a methyl group or a phenyl group; Spirobifluorene group; A quinazoline group substituted with a phenyl group; Benzoquinazolin group substituted by the phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Carbazole groups unsubstituted or substituted with a phenyl group; A benzocarbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; Benzothienopyrimidine group substituted by the phenyl group; Benzopurpyrimidine group substituted by the phenyl group; Or a benzoquinazolin group substituted with a phenyl group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent naphthyl group.

In one embodiment of the present specification, L1 and L2 are direct bonds.

In one embodiment of the present specification, the compound of Formula 1 is selected from the following structural formulas.

.

.

The compound according to an exemplary embodiment of the present application may be prepared by the manufacturing method described below.

For example, the compound of Formula 1 may be prepared in the core structure as shown in Schemes 1 to 10. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

Compounds of the present invention are representative of the Buchwald-Hartwig coupling reaction, Heck coupling reaction, Suzuki coupling reaction, Miyaura borilation (Miyaura) Borylation) and the like.

Scheme 1

1) Preparation of Chemical Formula a-2

200.0 g (1.0 eq) of naphthalen-2-amine, 443.25 g (1.0 eq) of 1-bromo-4-chloro-2-iodobenzene, 201.3 g (1.5 eq) of NaOtBu, 3.13 g (0.01) of Pd (OAc) ₂ eq) and 8.08 g (0.01 eq) of Xantphos, dissolved in 4 L of 1,4-dioxane, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in ethyl acetate, washed with water, and then depressurized to remove about 70% of the solvent. Hexane was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 283.41 g of a compound a-2 (yield 61%). [M + H] = 333

2) Preparation of Chemical Formula a-1

Pd (t-Bu ₃ P) _{2 to} 283.41 g (1.0 eq) 3.90 g (0.01 eq) and 211.11 g (2.00 eq) of K ₂ CO ₃ were added to 2 L of diethylacetamide and refluxed to stir. After 3 hours the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, washed with water, and the resulting solution was concentrated under reduced pressure. The crystals were dropped, cooled, and filtered. This was purified by column chromatography to give 74.97 g (39% yield) of Chemical Formula a-1. [M + H] = 252

3) Preparation of Chemical Formula a

a-1 (74.97 g, 298 mmol) and bis (pinacolato) diborane (113.5 g, 447 mmol), potassium acetic acid (73.1 g, 745 mmol), Pd (dba) ₂ (1.71 g, 3.0 mmol), PCy ₃ (1.67 g, 6.0 mmol) were added, 1,4-dioxane (750 ml) was added thereto, and the mixture was stirred under reflux for about 12 hours. After the reaction was cooled to room temperature and filtered. The organic layer was separated from the filtrate, the organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain a compound of Formula a (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 62 g (yield: 85%) of -5H-benzo [b] carbazole) were obtained. [M + H] = 344

Scheme 2 Preparation of Chemical Formula b

Formula b (2- (4,4) in the same manner as in the preparation of Formula a using 2-bromo-4-chloro-1-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] = 344

Scheme 3 Preparation of Chemical Formula c

Formula c (1- (4,4) in the same manner as in the preparation of Formula a using 2-bromo-1-chloro-3-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene , 5,5, -tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] = 344

Scheme 4 Preparation of Chemical Formula d

Formula 1 (4- (4,4) in the same manner as in the preparation of formula a using 1-bromo-3-chloro-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] = 344

Scheme 5 Preparation of Chemical Formula e

Preparation of formula a using 4-chloronaphthalen-2-amine instead of naphthalen-2-amine and 1-bromo-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene Formula e (11- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized in the same manner as the method. . [M + H] = 344

Scheme 6 Preparation of Formula f

A method of preparing Formula A using 5-chloronaphthalene-2-amine instead of naphthalene-2-amine and 1-bromo-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene The formula f (10- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole was synthesized by the method. H] = 344

Scheme 7 Preparation of Chemical Formula g

6-chloronaphthalene-2-amine instead of naphthalene-2-amine, 1-bromo-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene, and the like The formula g (9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized by the method. [M + H] = 344

Scheme 8 Preparation of Chemical Formula h

Instead of naphthalen-2-amine, 7-chloronaphthalene-2-amine, 1-bromo-2-chloro-2-iodobenzene instead of 1-bromo-2-iodobenzene, and the like The formula h (8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized by the method. [M + H] = 344

Scheme 9 Preparation of Chemical Formula i

8-chloronaphthalene-2-amine instead of naphthalene-2-amine, 1-bromo-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene The formula i (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized by the method. [M + H] = 344

Scheme 10 Preparation of Chemical Formula j

1-chloronaphthalene-2-amine instead of naphthalene-2-amine, 1-bromo-2-iodobenzene instead of 1-bromo-4-chloro-2-iodobenzene The formula j (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized by the method. [M + H] = 344

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic EL device of the present invention, the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer has a thickness of 100 kPa to 600 kPa.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the thickness of the light emitting layer is 300 kPa to 500 kPa.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer is a red light emitting layer.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a red host.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer further includes a dopant.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and the dopant in a weight ratio of 1: 1 to 100: 1.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer further includes an iridium-based dopant.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, the light emitting layer includes a dopant, and the dopant material is selected from the following structural formulas.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, the hole injection layer, a hole transport layer or a hole injection and transport layer comprises the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer or an electron injection and transport layer, and the electron injection layer, an electron transport layer or an electron injection and transport layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron injection and transport layer, and the electron injection and transport layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron suppression layer or a hole blocking layer, and the electron suppression layer or a hole blocking layer includes the compound.

In one embodiment of the present application, the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound.

In an exemplary embodiment of the present application, the two or more organic material layers are selected from the group consisting of a hole injection layer, a hole transport layer, an electron suppression layer, a hole blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, Can be.

In an exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

 In another exemplary embodiment, the organic EL device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer (3).

2 shows the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the electron suppression layer 7, the light emitting layer 3, the hole blocking layer 8, the electron injection and transport layer 9 The structure of the organic electroluminescent element in which the cathode and the cathode 4 are sequentially stacked is illustrated. In this structure, the compound may be included in the light emitting layer (3).

In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.

The organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As an electron transport material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is a material having high mobility to electrons. Suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic electroluminescent device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

The preparation of the compound represented by Chemical Formula 1 and the organic electroluminescent device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Production Example >

Synthesis Example 1

15.7 g (1.1 eq) of formula a, 10 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.11 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 150 ml of dioxane and dissolved in 50 ml of water. 17.6 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 13.3 g (76% yield) of compound 1-1. [M + H] = 422

Compound 1-1 12.5 g (1.1 eq), 2-chloro-4-phenylquinazoline 6.5 g (1.0 eq), K ₃ PO ₄ 11.47 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.03 g ( 0.002 eq) was dissolved in 120 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.8 g (yield 75%) of compound 1. [M + H] = 626

Synthesis Example 2

18.8 g (1.1 eq) of formula b, 12 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.13 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 170 ml of dioxane and dissolved in 50 ml of water. 21.2 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 15 g (yield 71%) of compound 9-1. [M + H] = 422

14.4 g (1.1 eq), 2-bromo-9-phenyl-9H-carbazole 10 g (1.0 eq), 13.17 g (2.0 eq) K ₃ PO ₄ , Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) was dissolved in 150 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 14.8 g (72% yield) of compound 9. [M + H] = 663

Synthesis Example 3

18.8 g (1.1 eq) of formula c, 12 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.13 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 170 ml of dioxane and dissolved in 50 ml of water. 21.2 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 15 g (yield 71%) of compound 33-1. [M + H] = 422

14.4 g (1.1 eq), 3-bromodibenzo [b, d] furan 10 g (1.0 eq), K ₃ PO ₄ 17.18 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.04 g (0.002 eq) was dissolved in 150 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 17.3 g (73% yield) of compound 33. [M + H] = 588

Synthesis Example 4

18.8 g (1.1 eq) of formula d, 12 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.13 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 170 ml of dioxane and dissolved in 50 ml of water. 21.2 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16.1 g (yield 77%) of compound 48-1. [M + H] = 422

15.6 g (1.1 eq) of Formula 48-1, 10 g (1.0 eq) of 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine, and 14.3 g of K ₃ PO ₄ (2.0) eq) and Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) were dissolved in 150 ml of xylene and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16.7 g (73% yield) of compound 48. [M + H] = 682

Synthesis Example 5

E 18.8 g (1.1 eq), 12 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.13 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 170 ml of dioxane and dissolved in 50 ml of water. 21.2 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16 g (yield 76%) of compound 60-1. [M + H] = 422

15.9 g (1.1 eq) 2-chloro-4-phenylbenzo [h] quinazoline 10 g (1.0 eq), K ₃ PO ₄ 14.6 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.04 g (0.002 eq) was dissolved in 150 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 17.2 g (74% yield) of compound 60. [M + H] = 676

Synthesis Example 6

Formula f 23.3 g (1.1 eq), 2- (2-chloroquinazolin-4-yl) -9-phenyl-9H-carbazole 25 g (1.0 eq), Pd (t-Bu ₃ P) ₂ 0.16 g ( 0.005 eq) was added to 200 ml of dioxane and 26.1 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added to reflux and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 28.1 g (yield 78%) of compound 66-1. [M + H] = 587

27.7 g (1.1 eq) 4-bromobiphenyl 10 g (1.0 eq), K ₃ PO ₄ 18.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.04 g (0.002 eq) It melt | dissolved in 150 ml of ethylene (Xylene), it refluxed, and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 21.3 g (yield 67%) of compound 66. [M + H] = 739

Synthesis Example 7

31.4 g (1.1 eq), 20 g (1.0 eq) of 2-chloro-4-phenylquinazoline, 0.21 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 270 ml of dioxane and dissolved in 80 ml of water. 35.3 g (2.0 eq) of K ₃ PO ₄ was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 25 g (yield%) of compound 70-1. [M + H] = 422

17.0 g (1.1 eq) 2-bromo-9,9-dimenyl-9H-fluorene 10 g (1.0 eq), K ₃ PO ₄ 18.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.04 g (0.002 eq) was dissolved in 180 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16 g (yield 76%) of compound 70. [M + H] = 614

Synthesis Example 8

16.6 g (1.1 eq), 15 g (1.0 eq) of 2-chloro-4- (phenanthren-2-yl) quinazoline, 0.11 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ 18.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 19.1 g (71% yield) of compound 89-1. [M + H] = 522

18.3 g (1.1 eq) bromobenzene 5 g (1.0 eq), K ₃ PO ₄ 13.5 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) Xylene) was dissolved in 160 ml and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 15.1 g (79% yield) of compound 89. [M + H] = 598

Synthesis Example 9

13.1 g (1.1 eq) of formula i, 12 g (1.0 eq) of 2-chloro-4- (dibenzo [b, d] thiophen-2-yl) quinazolin, 0.09 g of Pd (t-Bu ₃ P) ₂ (0.005 eq) was added to 170 ml of dioxane, 14.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.8 g (76% yield) of compound 108-1. [M + H] = 522

12.6 g (1.1 eq) 2-bromo-9-phenyl-9H-carbazole 7 g (1.0 eq), K ₃ PO ₄ 9.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.02 g (0.002 eq) was dissolved in 110 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 11.2 g (yield 67%) of the compound 108. [M + H] = 769

Synthesis Example 10

17.9 g (1.1 eq) of formula j, 15 g (1.0 eq) of 2-chloro-4,6-diphenylquinazoline, 0.12 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were added to 160 ml of dioxane 14.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16.2 g (69%) of compound 114-1. [M + H] = 498

11.9 g (1.1 eq) 2-bromo-9-phenyl-9H-carbazole 7 g (1.0 eq), K ₃ PO ₄ 9.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.02 g (0.002 eq) was dissolved in 110 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.3 g (76% yield) of compound 114. [M + H] = 739

Synthesis Example 11

Formula 1-1 14.4 g (1.1 eq) 3-bromo-9-phenyl-9H-carbazole 10 g (1.0 eq), K ₃ PO ₄ 13.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) was dissolved in 180 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 15.4 g (yield 75%) of compound 152. [M + H] = 663

Synthesis Example 12

14.4 g (1.1 eq) 2-chloro-4,6-diphenyl-1,3,5-triazine 10 g (1.0 eq), K ₃ PO ₄ 15.9 g (2.0 eq), Pd (t 0.04 g (0.002 eq) of -Bu ₃ P) ₂ was dissolved in 180 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 17.3 g (yield 71) of compound 159. [M + H] = 653

Synthesis Example 13

Formula c 24 g (1.1 eq), 7-([1,1'-biphenyl] -4-yl) -2-chloro-4-phenylquinazolin 25 g (1.0 eq), Pd (t-Bu ₃ P ) ₂ 0.17 g (0.005 eq) was added to 160 ml of dioxane, 27 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 25 g (yield 68%) of compound 166-1. [M + H] = 575

19.6 g (1.1 eq) 3-bromo-9-phenyl-9H-carbazole 10 g (1.0 eq), K ₃ PO ₄ 13.2 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) was dissolved in 150 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 18.5 g (73% yield) of compound 166. [M + H] = 816

Synthesis Example 14

Formula g 23.2 g (1.1 eq), 2-chloro-6- (dibenzo [b, d] furan-4-yl) -4-phenylquinazoline 25 g (1.0 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.005 eq) was added to 200 ml of dioxane and 26 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added to reflux and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 25 g (69% yield) of compound 173-1. [M + H] = 588

Formula 173-1 24.1 g (1.1 eq) 2-chloro-4,6-diphenyl-1,3,5-triazine 10 g (1.0 eq), K ₃ PO ₄ 15.9 g (2.0 eq), Pd (t 0.04 g (0.002 eq) of -Bu ₃ P) ₂ was dissolved in 200 ml of xylene, refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 19.7 g (64% yield) of compound 173. [M + H] = 820

Synthesis Example 15

Formula g 23.8 g (1.1 eq), 2-chloro-4-phenyl-7- (pyridin-2-yl) quinazolin 20 g (1.0 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.005 eq) Was added to 200 ml of dioxane, 26.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added thereto, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer in which the salt was dissolved was removed and the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 21.2 g (68% yield) of compound 179-1. [M + H] = 499

17.5 g (1.1 eq) bromobenzene 5 g (1.0 eq), K ₃ PO ₄ 13.5 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.03 g (0.002 eq) Xylene) was dissolved in 200 ml and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 14.8 g (yield 81%) of compound 179. [M + H] = 575

Comparative example  One

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following HI-1 compound was formed to a thickness of 1150 kPa as the hole injection layer on the prepared ITO transparent electrode, but the following A-1 compound was p-doped at a concentration of 1.5% (weight ratio). The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a film thickness of 800 kPa. Subsequently, the following EB-1 compound was vacuum deposited on the hole transport layer with a film thickness of 150 Pa to form an electron suppressing layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited on the EB-1 deposited film at a weight ratio of 98: 2 to form a red light emitting layer having a thickness of 400 Pa. A hole blocking layer was formed by vacuum depositing the following HB-1 compound on the light emitting layer with a film thickness of 30 GPa. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 2: 1 to form an electron injection and transport layer at a thickness of 300 Pa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited in a thickness of 12 Å in order to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

Example  1 to 15

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of RH-1 in the organic light-emitting device of Comparative Example 1.

Comparative example  2 to 10

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of RH-1 in the organic light-emitting device of Comparative Example 1.

When the current was applied to the organic light emitting diodes manufactured in Examples 1 to 15 and Comparative Examples 1 to 10, voltage, efficiency, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (5000 nit).

division matter Driving voltage (V) Efficiency (cd / A) Life span T95 (hr) Luminous color Comparative Example 1 RH-1 4.45 32.2 162 Red Example 1 Compound 1 4.15 38.5 267 Red Example 2 Compound 9 4.02 36.7 272 Red Example 3 Compound 33 3.99 37.8 284 Red Example 4 Compound 48 4.09 39.7 271 Red Example 5 Compound 60 4.11 38.3 260 Red Example 6 Compound 66 4.10 35.5 267 Red Example 7 Compound 70 4.18 38.4 259 Red Example 8 Compound 89 4.10 38.0 263 Red Example 9 Compound 108 4.02 37.2 275 Red Example 10 Compound 114 4.16 35.3 264 Red Example 11 Compound 152 4.08 36.2 268 Red Example 12 Compound 159 4.03 37.1 280 Red Example 13 Compound 166 4.15 38.2 256 Red Example 14 Compound 173 4.11 38.1 273 Red Example 15 Compound 179 4.06 37.2 265 Red Comparative Example 2 RH-2 4.42 30.2 185 Red Comparative Example 3 RH-3 4.52 29.5 175 Red Comparative Example 4 RH-4 4.31 29.1 163 Red Comparative Example 5 RH-5 4.52 30.3 152 Red Comparative Example 6 RH-6 4.38 31.8 130 Red Comparative Example 7 RH-7 4.43 31.5 184 Red Comparative Example 8 RH-8 4.58 32.0 171 Red Comparative Example 9 RH-9 4.41 28.2 166 Red Comparative Example 10 RH-10 4.45 29.3 156 Red

When the electric current was applied to the organic light emitting element produced by Examples 1-15 and Comparative Examples 1-10, the result of Table 1 was obtained. The red organic light emitting device of Comparative Example 1 uses a material that is widely used in the prior art, and has a structure of using compound [EB-1] as an electron suppression layer and RH-1 / Dp-7 as a red light emitting layer. In Comparative Examples 2 to 10, organic light emitting diodes were manufactured by using RH-2 to RH-10 instead of RH-1. In the results of Table 1, when the compound of the present invention is used as a host of the red light emitting layer, the driving voltage is 7% to 10% lower than that of the comparative material, and the efficiency is increased by 10% to 20% or more, thereby increasing the red color in the host. We can see that energy transfer to the dopant works well. In addition, it can be seen that the life characteristics are improved up to two times or more while maintaining high efficiency. This can be judged to be because the compound of the present invention has higher stability to electrons and holes than the compound of Comparative Example. Therefore, when the compound of the present invention is used as a host of the red light emitting layer, it can be seen that the driving voltage, the light emission efficiency and the life characteristics of the organic light emitting device are improved.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron suppression layer
8: hole blocking layer
9: electron injection and transport layer

Claims (10)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
L 2 is a direct bond; Or a substituted or unsubstituted arylene group,
R1 to R7 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group Ring heterocyclic group,
m is an integer from 0 to 4, when m is 2 or more, R1 is the same as or different from each other,
n is an integer from 0 to 6, when n is 2 or more, R2 is the same as or different from each other,
0 ≦ m + n ≦ 9. The method according to claim 1, wherein at least one of R3, R5 and R6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. The compound of claim 1, wherein R 1 and R 2 are hydrogen. The method according to claim 1, wherein Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted triazine group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzothienopyrimidine group; Substituted or unsubstituted benzofurypyrimidine group; Or a substituted or unsubstituted benzoquinazolin group. The compound of claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond or a phenylene group. The compound of claim 1, wherein the compound of Formula 1 is selected from the following structural formulas:

A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 6. Phosphorescent organic electroluminescent device. The organic electroluminescent device according to claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic electroluminescent device according to claim 7, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The organic electroluminescent device according to claim 7, wherein the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.

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