WO2019022535A1 - Compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic electroluminescent device comprising same.

Description

Compound and organic electroluminescent device including same

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

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high 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 the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the 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, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

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

The present application provides a compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

Ar 1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L2 is a direct bond; Or a substituted or unsubstituted arylene group,

R 1 to R 7 are the same or different and are each independently selected from the group consisting of 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, A substituted or unsubstituted heterocyclic group,

m is an integer of 0 to 4, and when m is 2 or more, R1 is the same or different,

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

0? M + n? 9.

The present application also includes a first electrode; A second electrode facing 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 above-described compound.

The compound according to one embodiment of the present application is used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, to improve the light efficiency, and to improve the lifetime of the device by the thermal stability of the compound.

Fig. 1 shows 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 laminated.

Fig. 2 is a cross-sectional view showing a structure of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron restraining layer 7, a light emitting layer 3, a hole blocking layer 8, 9) and a cathode 4 are sequentially laminated on a substrate 1.

3 is a mass spectrum of Compound 1 according to one embodiment of the present invention.

4 is a mass spectrum of Compound 9 according to one embodiment of the present invention.

5 is a mass spectrum of Compound 33 according to one embodiment of the present invention.

[Description of Symbols]

1: substrate

2: anode

3: light emitting layer

4: cathode

5: Hole injection layer

6: hole transport layer

7: Electronic inhibiting layer

8: hole blocking layer

9: Electron injection and transport layer

Hereinafter, the present invention will be described in more detail.

The present invention provides a compound represented by the above formula (1).

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; An alkyl group; A cycloalkyl group; An alkenyl group; An alkoxy group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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, and the number of carbon atoms 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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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 has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

When the fluorenyl group is substituted,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, A pyridazinyl group, a pyridopyrimidinyl group, a pyridopyrimidinyl group, a pyridazinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophenyl group, a dibenzoyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzoimidazolyl group, A thiophenyl group, a benzofuranyl group, a dibenzofuranyl group; Benzosyl group; Dibenzosilyl groups; A phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenoxazinyl group, a condensed structure thereof, and the like, but are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In one embodiment of the present specification, at least one of R 3 to R 7 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, at least one of R 3, R 5 and R 6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, at least one of R 3, R 5 and R 6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and R4 and R7 are hydrogen.

In one embodiment of the present specification, at least one of R 3, R 5, and R 6 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, at least one of R 3, R 5, and R 6 is a phenyl group; A biphenyl group; Naphthyl group; An aryl group or a fluorene group substituted or unsubstituted with an alkyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with an aryl group; A benzocarbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, at least one of R 3, R 5, and R 6 is a phenyl group; A biphenyl group; Naphthyl group; A phenyl group or a fluorene group substituted or unsubstituted with a methyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with a phenyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R 3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R 3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, R 3 is a phenyl group; A biphenyl group; Naphthyl group; An aryl group or a fluorene group substituted or unsubstituted with an alkyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with an aryl group; A benzocarbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R 3 is a phenyl group; A biphenyl group; Naphthyl group; A phenyl group or a fluorene group substituted or unsubstituted with a methyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with a phenyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R5 and R6 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofurane group; A 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 or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; Naphthyl group; An aryl group or a fluorene group substituted or unsubstituted with an alkyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with an aryl group; A benzocarbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

In one embodiment of the present specification, R5 and R6 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; Naphthyl group; A phenyl group or a fluorene group substituted or unsubstituted with a methyl group; A spirobifluorene group; Phenanthrene; Triphenylene group; A carbazole group substituted or unsubstituted with a phenyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group; A dibenzofurane group; A dibenzothiophene group; Or a pyridine group.

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

In one embodiment of the present specification, R 2 is hydrogen or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R 2 is hydrogen or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, R 2 is hydrogen or a dibenzothiophene group.

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

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

In one embodiment of the present specification, Ar1 represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted benzoquinazoline group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzothienopyrimidine group; A substituted or unsubstituted benzopyrimidinyl group; Or a substituted or unsubstituted benzoquinazoline group.

In one embodiment of the present specification, Ar1 represents a phenyl group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A fluorene group substituted or unsubstituted with an alkyl group or an aryl group; A spirobifluorene group substituted or unsubstituted with an aryl group; A quinazoline group substituted or unsubstituted with an aryl group; A benzoquinazoline group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A carbazolyl group substituted or unsubstituted with an aryl group; A benzocarbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group substituted or unsubstituted with an aryl group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A benzothienopyrimidine group substituted or unsubstituted with an aryl group; A benzofuropyrimidine group substituted or unsubstituted with an aryl group; Or a benzoquinazoline group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Ar1 represents a phenyl group; A biphenyl group; A fluorene group substituted with an alkyl group or an aryl group; A spirobifluorene group; A quinazoline group substituted with an aryl group; A benzoquinazoline group substituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A carbazolyl group substituted or unsubstituted with an aryl group; A benzocarbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group; A dibenzothiophene group; A benzothienopyrimidine group substituted with an aryl group; A benzofuropyrimidine group substituted with an aryl group; Or a benzoquinazoline group substituted with an aryl group.

In one embodiment of the present specification, Ar1 represents a phenyl group; A biphenyl group; A fluorene group substituted with a methyl group or a phenyl group; A spirobifluorene group; A quinazoline group substituted with a phenyl group; A benzoquinazoline group substituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a phenyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group; A dibenzofurane group; A dibenzothiophene group; A benzothienopyrimidine group substituted with a phenyl group; A benzofuropyrimidine group substituted with a phenyl group; Or a benzoquinazoline group substituted with a phenyl group.

In one embodiment of the present invention, L 1 and L 2 are the same or different and are each independently a direct bond, or a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L 1 and L 2 are the same or different and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted bivalent naphthyl group.

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

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

The compound according to one embodiment of the present application can be produced by a production method described below.

For example, the compound of Chemical Formula 1 may have a core structure as shown in Reaction Schemes 1 to 10 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

The compounds of the present invention may be used in a typical reaction such as a Buchwald-Hartwig coupling reaction, a Heck coupling reaction, a Suzuki coupling reaction, a Miyaura coupling Borylation).

[Reaction Scheme 1]

1) Preparation of formula a-2

Naphthalene-2-amine 200.0 g (1.0 eq), 1- bromo-4-chloro-2-iodo-benzene, 443.25 g (1.0 eq), NaOtBu 201.3 g (1.5 eq), Pd (OAc) 2 3.13 g (0.01 eq), 8.08 g (0.01 eq) of Xantphos and 4 L of 1,4-dioxane, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in ethyl acetate, washed with water, and further decompressed to remove about 70% of the solvent. Again, hexane was added in reflux, the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 283.41 g (yield: 61%) of the compound a-2. [M + H] < + > = 333

2) Preparation of formula a-1

To 283.41 g (1.0 eq) of formula a-2 was added Pd (t-Bu ₃ P) ₂ 3.90 g (0.01 eq) of K ₂ CO _{3 and} 211.11 g (2.00 eq) of K ₂ CO _{3 were} placed in ₂ L of dimethylacetamide, refluxed and stirred. After 3 hours, the reaction mixture was poured into water, and crystals were dropped and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to precipitate crystals, which were then cooled and then filtered. This was purified by column chromatography to obtain 74.97 g (yield 39%) of the compound a-1. [M + H] < + > = 252

3) Preparation of formula a

(73.1 g, 745 mmol), Pd (dba) ₂ (1.71 g, 447 mmol), bis (pinacolato) diborane (113.5 g, 447 mmol) 3.0 mmol) and PCy ₃ (1.67 g, 6.0 mmol) were added, 1,4-dioxane (750 ml) was added, and the mixture was stirred under reflux for about 12 hours. After the reaction was completed, the solution was cooled to room temperature and filtered. The organic layer was separated from the filtrate, and the organic layer was distilled off under reduced pressure. The residue was purified by column chromatography to give the title compound a (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -5H-benzo [b] carbazole) (yield: 85%). [M + H] < + > = 344

[Reaction Scheme 2] Preparation of Formula b

Bromo-4-chloro-1-iodobenzene in place of 1-bromo-4-chloro-2-iodobenzene, the compound of formula b (2- , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

[Reaction Scheme 3] Preparation of Formula c

Bromo-1-chloro-3-iodobenzene in place of 1-bromo-4-chloro-2-iodobenzene, the compound of the formula c (1- 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

[Reaction Scheme 4] Preparation of formula d

Bromo-3-chloro-2-iodobenzene in place of 1-bromo-4-chloro-2-iodobenzene, the compound of formula d (4- , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

[Reaction Scheme 5] Preparation of Formula e

The title compound was prepared using 4-chloronaphthalene-2-amine instead of naphthalene-2-amine and 1-bromo-2-iodobenzene instead of 1- (11- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized . [M + H] < + > = 344

[Reaction Scheme 6] Preparation of Formula f

Bromo-2-iodobenzene instead of 5-chloronaphthalene-2-amine and 1-bromo-4-chloro-2-iodobenzene in place of naphthalene- 5H-benzo [b] carbazole was synthesized in the same manner as in [M + H] = 344

[Reaction Scheme 7] Preparation of Formula g

Bromo-2-iodobenzene instead of 6-chloronaphthalene-2-amine and 1-bromo-4-chloro-2-iodobenzene in place of naphthalene- (9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

[Reaction Scheme 8] Preparation of Formula h

Bromo-2-iodobenzene instead of 7-chloronaphthalene-2-amine and 1-bromo-4-chloro-2-iodobenzene in place of naphthalene- (8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

[Reaction Scheme 9] Preparation of Formula (i)

Bromo-2-iodobenzene instead of 8-chloronaphthalene-2-amine and 1-bromo-4-chloro-2-iodobenzene in place of naphthalene- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

Scheme 10 Preparation of Formula j

Bromo-2-iodobenzene in place of 1-chloronaphthalene-2-amine and 1-bromo-4-chloro-2-iodobenzene in place of naphthalene- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [b] carbazole) was synthesized. [M + H] < + > = 344

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

When a member is referred to herein as being " on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as " comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

The organic material layer of the organic electroluminescent device of the present application may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic electroluminescent device of the present invention, the organic electroluminescent device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, etc. 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 one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer has a thickness of 100 to 600 ANGSTROM.

In one embodiment of the present application, the organic layer includes a light emitting layer, and the thickness of the light emitting layer is 300 ANGSTROM to 500 ANGSTROM.

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

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

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

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

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

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

In one embodiment of the present application, the organic 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 one embodiment of the present application, the organic 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 one embodiment of the present application, the organic material layer includes a hole injecting layer, a hole transporting layer, or a hole injecting and transporting layer, and the hole injecting layer, the hole transporting layer, or the hole injecting and transporting layer includes the above compound.

In one embodiment of the present application, the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the above compound.

In one 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, electron transport layer or electron injection and transport layer includes the above compounds.

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

In one embodiment of the present application, the organic layer includes an electron suppressing layer or a hole blocking layer, and the electron suppressing layer or the hole blocking layer includes the compound.

In one embodiment of the present application, the organic electroluminescent device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

In one embodiment of the present application, the two or more organic compound layers are selected from two or more groups 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 and an electron injection layer .

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

In another embodiment, the organic electroluminescent device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic electroluminescent device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

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

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

FIG. 2 is a cross-sectional view showing the structure of the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the electron restraining layer 7, the light emitting layer 3, the hole blocking layer 8, ) And a cathode (4) are sequentially laminated on a transparent substrate (1). In such a structure, the compound may be included in the light-emitting layer (3).

In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron injecting and transporting layer.

The organic electroluminescent device of the present application can be produced by materials and methods known in the art, except that one or more of the organic layers include the compound of the present application, i.e., the compound.

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

For example, the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic electroluminescent device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic electroluminescent device can also be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (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 embodiment, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. 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 include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; 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 compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, and the like, but are not limited thereto.

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

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The preparation of the compound represented by 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.

< Manufacturing example >

&Lt; Synthesis Example 1 &

Formula a 15.7 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 10 g (1.0 eq), Pd (t-Bu 3 P) 2 0.11 g (0.005 eq) in dioxane into a 150 ml dissolved in water 50ml 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 containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 13.3 g (yield 76%) of Compound 1-1. [M + H] &lt; + &gt; = 422

Compound 1-1 12.5 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 12.8 g (yield 75%) of Compound 1. [M + H] &lt; / RTI &gt; = 626

&Lt; Synthesis Example 2 &

Formula b 18.8 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 12 g (1.0 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) in dioxane into a 170 ml dissolved in water 50ml 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 containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 15 g (yield: 71%) of Compound 9-1. [M + H] &lt; + &gt; = 422

Formula 9-1 14.4 g (1.1 eq), 2- bromo-9-phenyl -9H- carbazol 10 g (1.0 eq), K 3 PO 4 13.17 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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 14.8 g (yield 72%) of Compound 9. [M + H] &lt; + &gt; = 663

&Lt; Synthesis Example 3 &

Formula c 18.8 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 12 g (1.0 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) in dioxane into a 170 ml dissolved in water 50ml 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 containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 15 g (yield: 71%) of Compound 33-1. [M + H] &lt; + &gt; = 422

Formula 33-1 14.4 g (1.1 eq), 3- bromo-modify-benzo [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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.3 g (yield: 73%) of Compound 33. [M + H] = 588

&Lt; Synthesis Example 4 &

Formula d 18.8 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 12 g (1.0 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) in dioxane into a 170 ml dissolved in water 50ml 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 containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.1 g (yield 77%) of Compound 48-1. [M + H] &lt; + &gt; = 422

Formula 48-1 15.6 g (1.1 eq), 2- chloro-4-phenyl-benzo [4,5] thieno [3,2-d] pyrimidine 10 g (1.0 eq), K 3 PO 4 14.3 g (2.0 eq) and 0.03 g (0.002 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 150 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.7 g (yield 73%) of Compound 48. [M + H] &lt; / RTI &gt; = 682

&Lt; Synthesis Example 5 &

Formula e 18.8 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 12 g (1.0 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) in dioxane into a 170 ml dissolved in water 50ml 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 containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16 g (yield 76%) of Compound 60-1. [M + H] &lt; + &gt; = 422

Formula 60-1 15.9 g (1.1 eq) 2- chloro-4-phenyl-benzo [h] quinazolin-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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.2 g (yield: 74%) of Compound 60. [M + H] = 676

&Lt; Synthesis Example 6 &

25 g (1.0 eq) of Pd (t-Bu ₃ P) ₂ (0.1 eq.), 25 g (1.0 eq) of 2- (2-chloroquinazolin- 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 and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 28.1 g (yield 78%) of Compound 66-1. [M + H] &lt; + &gt; = 587

To a solution of 27.7 g (1.1 eq) of 4-bromobiphenyl, 1.0 eq of K ₃ PO _{4 and} 2.0 eq of Pd (t-Bu ₃ P) ₂ (0.002 eq) Was dissolved in 150 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 21.3 g (yield 67%) of Compound 66. [M + H] &lt; + &gt; = 739

&Lt; Synthesis Example 7 &

Formula g 31.4 g (1.1 eq), 2- chloro-4-phenyl-quinazoline 20 g (1.0 eq), Pd (t-Bu 3 P) 2 0.21 g (0.005 eq) in dioxane into a 270 ml dissolved in water 80ml K ₃ PO ₄ 35.3 g and the mixture was stirred under reflux by placing a (2.0 eq). After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 25 g (yield%) of Compound 70-1. [M + H] &lt; + &gt; = 422

Formula 70-1 17.0 g (1.1 eq) 2- bromo-9,9-di-Mesnil -9H- fluorene 10 g (1.0 eq), K 3 PO 4 18.2 g (2.0 eq), Pd (t-Bu 3 P) ₂ (0.02 g, 0.002 eq) was dissolved in 180 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16 g (yield: 76%) of Compound (70). [M + H] &lt; + &gt; = 614

&Lt; Synthesis Example 8 &

Formula h 16.6 g (1.1 eq), 2- chloro-4-a (phenanthrene-2-yl) quinazoline 15 g (1.0 eq), Pd (t-Bu 3 P) 2 0.11 g (0.005 eq) in dioxane 150 ml, and 18.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 19.1 g (yield 71%) of Compound 89-1. [M + H] &lt; + &gt; = 522

Xylene formula 89-1 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), refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 15.1 g (yield 79%) of Compound 89. [M + H] &lt; + &gt; = 598

&Lt; Synthesis Example 9 &

Formula i 13.1 g (1.1 eq), 2- chloro-4- (dibenzo [b, d] thiophene-2-yl) quinazoline 12 g (1.0 eq), Pd (t-Bu 3 P) 2 0.09 g (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, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 12.8 g (yield 76%) of Compound 108-1. [M + H] &lt; + &gt; = 522

Formula 108-1 12.6 g (1.1 eq) 2- bromo-9-phenyl -9H- carbazol-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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 11.2 g (yield 67%) of Compound 108. [M + H] &lt; / RTI &gt; = 769

&Lt; Synthesis Example 10 &

Formula j 17.9 g (1.1 eq), 2- chloro-4,6-diphenyl-quinazoline 15 g (1.0 eq), into a _{Pd (t-Bu 3 P)} 2 0.12 g (0.005 eq) in dioxane, 160 ml of water 14.7 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of toluene was added, and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.2 g (yield 69%) of Compound 114-1. [M + H] = 498

Formula 114-1 11.9 g (1.1 eq) 2- bromo-9-phenyl -9H- carbazol-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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 12.3 g (yield 76%) of Compound 114. [M + H] &lt; + &gt; = 739

&Lt; Synthesis Example 11 &

Formula 1-1 14.4 g (1.1 eq) 3- bromo-9-phenyl -9H- carbazol 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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 15.4 g (yield 75%) of Compound 152. [M + H] &lt; + &gt; = 663

&Lt; Synthesis Example 12 &

Formula 9-1 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 -Bu ₃ P) ₂ (0.04 g, 0.002 eq) was dissolved in 180 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.3 g (yield 71%) of Compound 159. [M + H] = 653

&Lt; Synthesis Example 13 &

25 g (1.0 eq) of Pd (t-Bu ₃ P (1 eq)), 25 g ) ₂ (0.15 g, 0.005 eq) were placed in 160 ml of dioxane, and 27 g (2.0 eq) of K ₃ PO ₄ dissolved in 50 ml of water was added and the mixture was refluxed and stirred. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 25 g (yield: 68%) of the compound 166-1. [M + H] &lt; + &gt; = 575

Formula 166-1 19.6 g (1.1 eq) 3- bromo-9-phenyl -9H- carbazol 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. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.5 g (yield: 73%) of Compound 166. [M + H] = 816

&Lt; Synthesis Example 14 &

Formula g 23.2 g (1.1 eq), 2- chloro-6- (dibenzo [b, d] furan-4-yl) -4-phenyl-quinazoline 25 g (1.0 eq), Pd (t-Bu 3 P) ₂ 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 thereto, followed by reflux and stirring. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 25 g (yield 69%) 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 -Bu ₃ P) ₂ (0.04 g, 0.002 eq) was dissolved in 200 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 19.7 g (yield: 64%) of Compound 173. [M + H] = 820

&Lt; Synthesis Example 15 &

Formula g 23.8 g (1.1 eq), 2- chloro-4-phenyl-7- (pyridin-2-yl) quinazoline 20 g (1.0 eq), Pd (t-Bu 3 P) 2 0.16 g (0.005 eq) put in 200 ml of dioxane was stirred under reflux by placing a _{K 3 PO 4 26.7 g (2.0} eq) was dissolved in 50ml water. After the reaction was completed after 2 hours, the water layer containing the salt was removed, and the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 21.2 g (yield: 68%) of the compound 179-1. [M + H] = 499

Xylene formula 179-1 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), refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 14.8 g (yield: 81%) of Compound 179. [M + H] &lt; + &gt; = 575

Comparative Example  One

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water, which was secondly filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was formed to a thickness of 1150 ANGSTROM as a hole injecting layer on the thus prepared ITO transparent electrode, and the following compound A-1 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 thickness of 800 ANGSTROM. Subsequently, EB-1 compound having a thickness of 150 ANGSTROM was vacuum deposited on the hole transport layer to form an electron inhibition layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vapor-deposited on the EB-1 vapor deposition film at a weight ratio of 98: 2 to form a 400 Å-thick red light emitting layer. HB-1 compound was vacuum deposited on the light emitting layer to a film thickness of 30 ANGSTROM to form a hole blocking layer. 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 injecting and transporting layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum having a thickness of 1,000 Å were sequentially deposited on the electron injecting and transporting layer 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 ^{- 7} to 5 x 10 &lt; ^-6 &gt; torr to manufacture an organic light emitting device.

Example  1 to 15

An organic luminescent device was prepared in the same manner as in Comparative Example 1, except that the compound shown in the following Table 1 was used in place of RH-1 in the organic luminescent device of Comparative Example 1.

Comparative Example  2 to 10

An organic luminescent device was prepared in the same manner as in Comparative Example 1, except that the compound shown in the following Table 1 was used in place of RH-1 in the organic luminescent device of Comparative Example 1.

The voltage, efficiency, and lifetime of the organic light emitting device manufactured in Examples 1 to 15 and Comparative Examples 1 to 10 were measured. The results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

division	matter	The driving voltage (V)	Efficiency (cd / A)	Life 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 current was applied to the organic light-emitting devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 10, the results shown in Table 1 were obtained. In the red organic light emitting device of Comparative Example 1, a commonly used material was used, and a compound [EB-1] was used as an electron restraining layer and RH-1 / Dp-7 was used as a red light emitting layer. In Comparative Examples 2 to 10, organic light emitting devices were manufactured using RH-2 to RH-10 instead of RH-1. When the compound of the present invention was used as a host of the red light emitting layer, the driving voltage was lowered by 7% to 10% and the efficiency was increased by 10% to 20% It was found that the energy transfer to the red dopant was performed well. It was also found that the lifetime characteristics were improved by at least two times while maintaining high efficiency. This can be judged from the fact that the compound of the present invention has higher stability against electrons and holes than the compound of the comparative example. Therefore, when the compound of the present invention is used as a host of the red luminescent layer, it can be confirmed that the driving voltage, luminescent efficiency and lifetime characteristics of the organic luminescent device are improved.

Claims (10)

1. A compound represented by the following formula (1):

   [Chemical Formula 1]

   

   In Formula 1,

   Ar 1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

   L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

   L2 is a direct bond; Or a substituted or unsubstituted arylene group,

   R 1 to R 7 are the same or different and are each independently selected from the group consisting of 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, A substituted or unsubstituted heterocyclic group,

   m is an integer of 0 to 4, and when m is 2 or more, R1 is the same or different,

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

   0? M + n? 9.
2. The compound according to claim 1, wherein at least one of R 3, R 5, and R 6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
3. 2. The compound of claim 1, wherein R1 and R2 are hydrogen.
4. [3] The compound according to claim 1, wherein Ar &lt; 1 &gt; is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted benzoquinazoline group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzothienopyrimidine group; A substituted or unsubstituted benzopyrimidinyl group; Or a substituted or unsubstituted benzoquinazoline group.
5. 2. The compound according to claim 1, wherein L1 and L2 are the same or different from each other, and each independently is a direct bond or a phenylene group.
6. The compound according to claim 1, wherein the compound of formula (1) is selected from the following structural formulas:

   

   

   

   

   
7. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one layer of the organic compound layer comprises the compound according to any one of claims 1 to 6 Organic electroluminescent device.
8. The organic electroluminescent device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.
9. The organic electroluminescent device according to claim 7, wherein the organic compound 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.
10. [Claim 7] The organic electroluminescent device according to claim 7, wherein the organic compound layer comprises 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 comprises the compound.

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