KR101983340B1 - Heterocyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

Description

TECHNICAL FIELD [0001] The present invention relates to a heterocyclic compound and an organic light emitting device using the heterocyclic compound. [0002]

The present invention relates to heterocyclic compounds and organic light emitting devices using the same.

This specification claims the benefit of Korean Patent Application No. 10-2016-004515, filed on April 12, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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.

International Patent Application Publication No. 2003-012890

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

An embodiment of the present invention provides a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1, R1 and R2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted amine group,

At least one of R 1 and R 2 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted amine group,

R3 and R4 are the same or different from each other and each independently hydrogen or deuterium,

Ra to Re are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

a is an integer of 1 to 3, b is 1 or 2, c to e are integers of 1 to 4, and when a to e are 2 or more, the substituents in the parentheses are the same as or different from each other.

The present application also includes a 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 above-described heterocyclic compound.

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

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated.
2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated FIG.
3 is a mass spectrum of Compound 1. Fig.
4 is a ¹ H-NMR spectrum of Compound 1. Fig.
5 is the COZY and NOESY NMR spectra of compound 1.
6 is a mass spectrum of Compound 2. Fig.
7 is a ¹ H-NMR spectrum of Compound 2. Fig.
Figure 8 is the COZY and NOESY NMR spectra of compound 2.
9 is a mass spectrum of Compound 3. Fig.
10 is a mass spectrum of Compound 4. FIG.
11 is a mass spectrum of Compound 5. Fig.
12 is a ¹ H-NMR spectrum of Compound 5.
13 shows the COZY and NOESY NMR spectra of Compound 5.
14 is a mass spectrum of Compound 3. Fig.
15 is a mass spectrum of Compound 18. Fig.

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

The present invention provides a heterocyclic 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; A nitro group; A hydroxy group; An alkyl group; A cycloalkyl group; An alkenyl group; An alkoxy group; A substituted or unsubstituted phosphine oxide 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, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, 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.

,

,

,

,

,

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

,

,

,

,

,

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

), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기; 벤조실롤기, 디벤조실롤기, 페난트롤리닐기(phenanthrolinyl group), 이소옥사졸릴기, 티아디아졸릴기페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대,

,

등이 있다.In the present specification, the heterocyclic group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, Si and S have. 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, Group, an acridyl group, a hydroacridyl group (e.g.,

), A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyrazinyl group, an isoquinolinyl group , An indole group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, A furanyl group; A benzoxyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzothiazolyl group, no. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

,

.

In the present specification, the aryl group in the arylalkyl group, arylalkenyl group, alkylaryl group and arylamine group can be applied to the description of the aryl group described above.

In the present specification, the alkyl group, the alkylaryl group and the alkyl group in the alkylamine group may be the same as the alkyl group described above.

In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.

In the present specification, the alkenyl group in the arylalkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

In one embodiment of the present specification, Ra to Re are hydrogen.

In one embodiment of the present invention, the formula (1) is represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3), the definitions of R 1 and R 2 are as shown in general formula (1).

In one embodiment of the present specification, R 1 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R1 is a phenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, R1 is a dibenzofurane group.

In one embodiment of the present specification, R < 1 > is a substituted or unsubstituted amine group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted arylamine group.

In one embodiment of the present specification, R 1 is an arylamine group substituted or unsubstituted with a heteroaryl group.

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

In one embodiment of the present invention, R 2 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R 2 is a phenyl group.

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

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

In one embodiment of the present specification, R 2 is a dibenzofurane group.

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

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

In one embodiment of the present specification, R 2 is an arylamine group substituted or unsubstituted with a heteroaryl group.

In one embodiment of the present invention, the compound of formula (1) is represented by any one of the following formulas (4) to (9).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the general formulas (4) to (9), the definitions of R 1 and R 2 are as shown in general formula (1).

In one embodiment of the present disclosure, at least one of R1 and R2 is selected from the following formulas. In the following structural formula, the dotted line means a bonding site with the formula (1).

In one embodiment of the present invention, at least one of R 1 and R 2 may be represented by -L-Ar, L is a direct bond, substituted or unsubstituted arylene group, Ar is substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present disclosure, L is a direct bond.

According to one embodiment of the present disclosure, L is a phenylene group.

이다.According to one embodiment of the present disclosure,

to be.

이다. According to one embodiment of the present disclosure,

to be.

According to one embodiment of the present invention, R 1 or R 2 in the above formulas 4 to 9 is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

According to one embodiment of the present invention, R1 in the formula (4) is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

According to another embodiment, R 2 in the formula (5) is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

According to another embodiment, R2 in Formula 6 is represented by -L-Ar, and L and Ar are selected in Tables 1 to 3 below.

According to another embodiment, R 1 in formula (7) is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

According to another embodiment, R 2 in formula (8) is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

According to another embodiment, R 2 in the above formula (9) is represented by -L-Ar, and L and Ar are selected from the following Tables 1 to 3.

[Table 1]

[Table 2]

[Table 3]

In the present specification, the numbers of the compounds having substituents in [Table 1] to [Table 3] are denoted by the symbols denoted by # in the above [Table 1] to [Table 3] . For example, when the compound is represented by the formula (4) and the substituent is 1 A, the compound is represented by the formula 4-1A and the structure is as follows.

[Compound 4-1A]

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

<Reaction Scheme 1>

1) Synthesis of intermediate A1

100.0 g (1.0 eq) of 2-chloro-9H-carbazole, 1a and 168.4 g (1-bromo-2- 1.2 eq), CuI 18.9 g (0.2 eq), 1,10-phenanthroline 17.9 g (0.2 eq) and KOAc 83.5 g (3.0 eq) were added to 1000 ml of xylene and refluxed and stirred . After the reaction was completed, the mixture was cooled to room temperature and then the copper powder was removed by filtration. The solution in which the product was dissolved was depressurized to remove all of the solvent. Then, the solution was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent. The product was purified using column chromatography. Intermediate A-1, 130.1 g (yield 74%) was obtained. [M + H] &lt; + &gt; = 355

2) Synthesis of compound of intermediate A1

In a nitrogen atmosphere, the intermediate A-1 was added to a 2000 ml round-bottomed flask, and the mixture was completely dissolved in 700 ml of tetrahydrofuran. After the temperature was lowered to -78, 2.1 eq of n-BuLi was added and stirred for 1 hour. (1c) 1.0 eq is slowly added dropwise over 30 minutes. After 2 hours, the temperature is adjusted to room temperature, and 200 ml of water is added to terminate the reaction. The aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol and chloroform to obtain 115.0 g (yield 69%) of Intermediate A1. [M + H] = 458

3) Synthesis of compound of intermediate A2

To a 1000 ml round-bottomed flask under nitrogen, 300 ml of intermediate A1 and acetic acid were added, 1.3 ml of H ₂ SO ₄ was added slowly, and the mixture was heated and stirred for 2.5 hours. The temperature is lowered to room temperature and the precipitated solid is filtered and washed with water. The filter cake is dissolved in 1L of chloroform, washed with water, and then the organic layer is separated to remove the solvent. 30.2 g (yield 66%) of Intermediate A2 was obtained using tetrahydrofuran and ethyl acetate. [M + H] &lt; + &gt; = 440

<Reaction Scheme 2>

1) Synthesis of intermediate 2b

A mixture of 100.0 g (1.0 eq) of 2-bromo-7-chloro-9H-carbazole, 2a and 47.8 g (1.1 eq) of phenyl boronic acid _{Pd (PPh 3) 4 8.2 g} (0.02 eq), the _{K 2 CO 3 147.8 g (3.0} eq) dissolved in water was stirred and placed under reflux in 1000 ml THF. After 8 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography to obtain 86.5 g (yield 77%) of Intermediate 2b as a white solid. [M + H] &lt; + &gt; = 278

2) Synthesis of intermediate B-1

110.2 g (yield 82%) of Intermediate B-1 was prepared in the same manner as Intermediate A-1 except that Intermediate 2b was used instead of Intermediate 1a. [M + H] &lt; + &gt; = 432

3) Synthesis of intermediate B1

92.0 g (yield: 68%) of Intermediate Compound B1 was prepared in the same manner as Intermediate A1 except that Intermediate B-1 was used instead of Intermediate A-1. [M + H] &lt; + &gt; = 534

4) Synthesis of intermediate B2

30.4 g (Yield: 68%) of Intermediate Compound B2 was prepared in the same manner as Intermediate A2 except that Intermediate B1 was used instead of Intermediate Al. [M + H] &lt; + &gt; = 516

5) Synthesis of intermediate B3

(1.2 eq) of bis (pinacolato) diboron, 1.0 g (0.03 eq) of Pd (dba) 2, 0.95 g (0.06 eq) of PCy ₃ and 17.4 g (3.0 eq) of KOAc were added to 30.4 g eq) was dissolved in 350 mL of dioxane, refluxed, and stirred for 9 hours. After completion of the reaction was confirmed by TLC, the base was removed by filtration, and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain 30.5 g (yield: 85%) of intermediate B3. [M + H] = 608

Subsequently, the compounds of the present invention were further synthesized using Buchwald-Hartwig coupling reaction or Suzuki coupling reaction with intermediates A1, A2, B1 to B3.

The present invention also provides an organic light emitting device comprising the above-described compound.

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 light emitting 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 light emitting device of the present invention, the organic light emitting device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting 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 heterocyclic compound.

In one embodiment of the present application, the thickness of the organic material layer is 1 ANGSTROM to 1000 ANGSTROM, more preferably 1 ANGSTROM to 500 ANGSTROM.

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material.

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material, and further includes another host material.

In one embodiment of the present application, the organic layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound as a host material, and further includes another host material, 9 to 9: 1.

In one embodiment of the present application, the organic layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound as a host material, and further includes another host material, 5 &lt; / RTI &gt;

In one embodiment of the present application, the other host material is a material comprising a carbazole or carbazole fused ring compound.

In one embodiment of the present application, the other host material is a material comprising a carbazole or dihydroindenocarbazole.

In one embodiment of the present application, the other host material may be represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In Formula (A), R100 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present application, R100 is an aryl group substituted with a heterocyclic group substituted with an aryl group.

In one embodiment of the present application, R100 is a phenyl group, or a phenyl group substituted with a triazine group substituted with a biphenyl group.

In one embodiment of the present application, the compound of formula (A) is a compound represented by the following structural formula.

In the formula (B), R200 and R201 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently a substituted or unsubstituted aryl group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted fluorene group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted fluorene group, and the "substituted or unsubstituted" substituent is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group, an alkoxy group, or an aryl group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted fluorene group means that the substituent of the "substituted or unsubstituted" is substituted or unsubstituted with cyano group, F, methyl group, methoxy group, phenyl group, naphthyl group or phenanthrene group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present application, R200 and R201 are the same or different from each other and are each independently a phenyl group; Or a biphenyl group.

In one embodiment of the present application, R200 is a phenyl group, and R201 is a biphenyl group.

In one embodiment of the present application, the compound of formula (B) is a compound selected from the following structural formulas.

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

In one embodiment of the present application, the dopant compound is a phosphorescent dopant.

In one embodiment of the present application, the dopant compound is an iridium complex.

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 compound in a ratio of 100: 1 to 5: 5.

In one embodiment of the present application, the dopant compound can be selected from the following structural formulas, but is not limited thereto.

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

In one embodiment of the present application, the organic layer includes a hole transporting layer, and the hole transporting layer includes the heterocyclic compound.

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

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

In one embodiment of the present application, the organic light emitting 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; And 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, and at least one of the two or more organic layers includes the heterocyclic compound.

In one embodiment of the present application, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

In one embodiment of the present application, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In the embodiment of the present application, when the heterocyclic compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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

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

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

1 shows a structure of an organic light emitting 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).

2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated Structure is illustrated. In such a structure, the compound may be contained in at least one of the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, and the electron transporting layer 7.

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 transporting layer.

The organic light emitting device of the present application may be manufactured 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.

 The organic light emitting 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 above compound, that is, the compound represented by the above formula (1).

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 light emitting 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 light emitting device may 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 material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection 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 material 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. Is 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 the 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 light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present application is not construed as being limited to the embodiments described below. The embodiments of the present application are provided to enable those skilled in the art to more fully understand the present invention.

Synthesis Example 1 Synthesis of Compound 1

1) Synthesis of Compound (1-1)

7.7 g (1.1 eq) of di ([1,1'-biphenyl] -4-yl) amine (1d) and 2.7 g (1.3 eq) of NaO t- And 0.33 g (0.03 eq) of bis (tri- tert -butylphosphine) palladium (0) was added thereto, and the mixture was refluxed and stirred. After 9 hours, the temperature is lowered to room temperature, filtered, and washed with water to remove the base. 13.7 g (yield 84%) of the compound 1-1 was obtained using tetrahydrofuran and ethyl acetate. [M + H] &lt; + &gt; = 743

2) Synthesis of Compound (1)

In a nitrogen atmosphere, Compound 1-1 and 150 ml of acetic acid were added, and 0.9 ml of H ₂ SO ₄ was slowly added thereto, followed by heating and stirring for 3 hours. The temperature is lowered to room temperature and the precipitated solid is filtered and washed with water. The filter cake is dissolved in 1L of chloroform, washed with water, and then the organic layer is separated to remove the solvent. Recrystallization was performed using N-methyl-2-pyrrolidone to obtain 10.3 g (yield 79%) of the compound 1. [M + H] = 725

Synthesis Example 2 Synthesis of Compound 2

Compound 1 of Synthesis Example 1 was synthesized except that N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- The compound 2 was prepared in the same manner as the preparation method.

Synthesis Example 3 Synthesis of Compound 3

(1f) of Synthesis Example 1 was used instead of N - ([1,1'-biphenyl] -2-yl) -9,9-dimethyl- The compound 3 was prepared in the same manner as the preparation method.

Synthesis Example 4 Synthesis of Compound 4

Except substituting 4'- ((4- (dibenzo [b, d] furan-4-yl) phenyl) amino) - [1,1'-biphenyl] -3-ylium , The compound 4 was prepared in the same manner as the compound 1 of Synthesis Example 1 was prepared.

Synthesis Example 5 Synthesis of Compound 5

1) Preparation of the compound of the formula 5-1

For intermediate A1 20.0 g (1.0 eq) dibenzo [b, d] furan-4-Daily acid (1h) 9.7 g (1.05 eq ), Pd (t-Bu 3 P) 2 0.45 g (0.02 eq) in water 23.1 g (1.5 eq) of dissolved K ₃ PO ₄ was added to 200 mL of dioxane, and the mixture was refluxed and stirred. After 10 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This is dissolved in CHCl _3, washed thoroughly with water, and then the base is removed. Tetrahydrofuran and ethyl acetate were recrystallized using a mixed solution to obtain 20.5 g (yield 78%) of Compound 5-1. [M + H] &lt; + &gt; = 590

2) Synthesis of Compound (5)

12.5 g (yield 63%) of Compound 5 was prepared in the same manner as Compound 1 was prepared, except that Compound 5-1 was used instead of Compound 1-1. [M + H] &lt; + &gt; = 572

Synthesis Example 6 Synthesis of Compound 6

Compound 6 was prepared in the same manner as Compound 5 of Synthesis Example 5 except that (9-phenyl-9H-carbazol-3-yl) boronic acid (1i) was used instead of Intermediate 1h.

Synthesis Example 7 Synthesis of Compound 7

The same procedure as in the preparation of the compound 5 of the synthesis example 5 was carried out except that [l, 1 ': 4', 1 "-terphenyl] -4-ylboronic acid (1j) .

Synthesis Example 8 Synthesis of Compound 8

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5- -Triazine (1k) was used in place of the compound (5), the compound 8 was prepared in the same manner as in the preparation of the compound 5 of the synthesis example 5.

Synthesis Example 9 Synthesis of Compound 9

1) Synthesis of Compound A-2

17.3 g (1.2 eq) of bis (pinacolato) diboron, 0.9 g (0.03 eq) of Pd (dba) ₂ , 0.9 g (0.06 eq) of PCy ₃ and 16.7 g (3.0 eq) of KOAc were added to 25.0 g eq) was placed in 300 mL of dioxane, refluxed, and stirred for 12 hours. After completion of the reaction was confirmed by TLC, the base was removed by filtration, and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was concentrated under reduced pressure, recrystallized using ethyl acetate, and dried to obtain 22.0 g (yield: 73%) of Compound A-2 B3. [M + H] = 532

2) Synthesis of Compound (9)

Compound A-2 11.0 g (1.0 eq ) and 2-chloro-4,6-diphenyl-pyrimidine (1l) Pd (PPh ₃₎ to _{6.1 g (1.1 eq) 4 0.5} g (0.02 eq), dissolved in water, K ₂ CO ₃ (8.6 g, 3.0 eq) were added to 100 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in _{CHCl 3} and completely washed with water. Recrystallization was performed using N-methyl-2-pyrrolidine to obtain 10.3 g (yield 78%) of the compound 9. [M + H] &lt; + &gt; = 636

Synthesis Example 10 Synthesis of Compound 10

1) Synthesis of Compound of Formula 10-1

The compound 10-l was synthesized in the same manner as in the intermediate 2b of the scheme 2 except that 2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine (1n) 1.

2) Synthesis of Compound (10)

Compound 10 was prepared in the same manner as Compound 9 except that Compound 10-1 was used instead of Intermediate 11.

Synthesis Example 11 Synthesis of Compound 11

Compound 11 was prepared in the same manner as Compound 1 except for using Intermediate B1 and N-phenyl- [1,1'-biphenyl] -4-amine (11a) instead of Intermediate A1 and Intermediate 1d .

Synthesis Example 12 Synthesis of Compound 12

Was prepared in the same manner as in the preparation of Compound 5, except that Intermediate B1 was used instead of Intermediate A1 and Intermediate 1h and [1,1 ': 3', 1 "-terphenyl] -5'-yl boronic acid (12b) Compound 12 was prepared.

Synthesis Example 13 Synthesis of Compound 13

Compound 13 was prepared in the same manner as Compound 5, except that Intermediate B1 and (4- (diphenylamino) phenyl) boronic acid (2c) were used instead of Intermediate Al and Intermediate 1h.

Synthesis Example 14: Synthesis of Compound 14

Intermediate B1 was prepared in the same manner as Intermediate A1 except that Intermediate B1 and (2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Phenyl) -1,3,5-triazine (2d), Compound 14 was prepared in the same manner as Compound 5 was prepared.

Synthesis Example 15: Synthesis of Compound 15

The compound 15 was prepared in the same manner as in the preparation of the compound 4-1 of the synthesis example 4, except that the intermediate B2 was used instead of the intermediate A1.

Synthesis Example 16 Synthesis of Compound 16

, Except that Intermediate B2 and dibenzo [b, d] thiophene-2-ylboronic acid (2e) were used in place of Intermediate A1 and Intermediate 1h, the compound 16.

Synthesis Example 17 Synthesis of Compound 17

The same procedure as in the preparation of the compound 5-1 of the synthesis example 5 was carried out except that Intermediate B2 and (9-phenyl-9H-carbazol-2-yl) boronic acid (2f) were used instead of Intermediate A1 and Intermediate 1h Compound 17 was prepared.

Synthesis Example 18 Synthesis of Compound 18

2-chloro-4, 6 in the intermediate B3 10.0 g (1.0 eq) of diphenyl-1,3,5-triazine (2g) 6.2 g (1.1 eq ), Pd (PPh 3) 4 0.38 g (0.02 eq) of K ₂ CO ₃ dissolved in water (6.8 g, 3.0 eq) was added to 110 mL of THF, and the mixture was refluxed and stirred. After 6 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and recrystallized using N-methyl-2-pyrrolidone to obtain 9.2 g (yield 71%) of Compound 18. [M + H] = 789

Synthesis Example 19 Synthesis of Compound 19

Compound 19 was prepared in the same manner as compound 18, except that 4-chloro-2,6-diphenylpyrimidine (2h) was used instead of 2g of intermediate.

Synthesis Example 20: Synthesis of Compound 20

Compound 20 was prepared in the same manner as compound 18, except that 2-chloro-4-phenylquinazoline (2i) was used instead of 2g of intermediate.

< Experimental Example  1>

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was 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 thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer.

The HT-1 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposition layer to a thickness of 50 Å to form an electron blocking layer.

Compound 1 and phosphorescent dopant Dp-25 were vacuum-deposited on the HT-2 deposited film at a weight ratio of 12% to form a light emitting layer having a thickness of 400 Å.

An ET-1 material was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM and an ET-2 material was co-deposited with a 2% weight ratio Li to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

<Experimental Example 2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 5 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 5>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 12 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 16 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 18 was used instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound H-1 was used instead of Compound 1 in Experimental Example 1

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound C-1 was used instead of Compound 1 in Experimental Example 1

&Lt; Comparative Example 3 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound C-3 was used instead of Compound 1 in Experimental Example 1

&Lt; Comparative Example 4 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound C-4 was used instead of Compound 1 in Experimental Example 1

<Experimental Example 9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2 and H-1 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 6 and H-1 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Experimental Example 11 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 7 and H-1 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 12>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 9 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 13>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 10 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 14 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 17 and H-1 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 19 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 5 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound H-1 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 6 >

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound H-1 and Compound C-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 7 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound H-1 and Compound C-3 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

compound Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color T95
(@ 20 mA / cm ² ) Experimental Example 1 One 2.69 70.3 green 61 Experimental Example 2 5 2.80 66.0 green 54 Experimental Example 3 6 2.73 65.5 green 60 Experimental Example 4 7 2.77 62.0 green 57 Experimental Example 5 8 2.81 64.4 green 55 Experimental Example 6 12 2.76 65.1 green 60 Experimental Example 7 16 2.86 67.8 green 56 Experimental Example 8 18 2.80 65.1 green 55 Experimental Example 9 2, H-1 3.22 76.9 green 171 Experimental Example 10 6, H-1 3.23 74.7 green 159 Experimental Example 11 7, H-1 3.25 73.6 green 170 Experimental Example 12 9, H-2 3.30 76.0 green 159 Experimental Example 13 10, H-2 3.24 74.9 green 166 Experimental Example 14 14, H-2 3.29 77.6 green 163 Experimental Example 15 17, H-1 3.30 75.0 green 157 Experimental Example 16 19, H-2 3.32 76.6 green 168 Comparative Example 1 H-1 3.01 60 green 40 Comparative Example 2 C-1 2.92 62 green 44 Comparative Example 3 C-3 2.88 64.1 green 47 Comparative Example 4 C-4 3.13 63.8 green 40 Comparative Example 5 H-1, H-2 3.52 67 green 140 Comparative Example 6 H-1, C-2 3.48 70 green 147 Comparative Example 7 H-1, C-3 3.40 72 green 150

The results of Table 4 show that compounds 1, 6, 7 and 12 of the present invention have advantages of low voltage and long life compared with compound H-1, which is a conventional green light emitting host material, It can be confirmed that it exhibits better performance in terms of efficiency and life span.

< Comparative Example  8>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was washed with ultrasonic waves in distilled water containing detergent. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was 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 thermally vacuum-deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

HT-1 compound was thermally vacuum-deposited on the HTL to form a hole transport layer, and an EB-1 compound was vacuum deposited on the HT-1 deposited layer to a thickness of 100 Å to form an electron blocking layer.

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

An ET-3 material and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum of 2000 Å thickness were sequentially deposited on the electron injection and transport layer to a thickness of 12 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. 10 ^-7 to 5? 10 ^-8 torr.

< Comparative Example  8>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was washed with ultrasonic waves in distilled water containing detergent. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was 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 thermally vacuum-deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

HT-1 compound was thermally vacuum-deposited on the HTL to form a hole transport layer, and an EB-1 compound was vacuum deposited on the HT-1 deposited layer to a thickness of 100 Å to form an electron blocking layer.

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

An ET-3 material and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum of 2000 Å thickness were sequentially deposited on the electron injection and transport layer to a thickness of 12 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

<Experiment 17>

An organic light emitting device was fabricated in the same manner as in Comparative Example 8, except that Compound 3 was used instead of HT-1 in Comparative Example 8.

<Experimental Example 18>

An organic light emitting device was fabricated in the same manner as in Comparative Example 8 except that Compound 4 was used instead of HT-1 in Comparative Example 8.

<Experimental Example 19>

An organic light emitting device was fabricated in the same manner as in Comparative Example 8, except that Compound 11 was used instead of HT-1 in Comparative Example 8.

<Experimental Example 20>

An organic light emitting device was fabricated in the same manner as in Comparative Example 8, except that Compound 13 was used instead of HT-1 in Comparative Example 8.

<Experimental Example 21>

An organic light emitting device was fabricated in the same manner as in Comparative Example 8, except that Compound 15 was used instead of HT-1 in Comparative Example 8.

compound Voltage V
(@ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 17 3 3.72 5.96 (0.139, 0.126) Experimental Example 18 4 3.75 6.05 (0.136, 0.126) Experimental Example 19 11 3.79 6.11 (0.137, 0.129) Experimental Example 20 13 3.76 5.94 (0.137, 0.126) Experimental Example 21 15 3.81 6.01 (0.138, 0.127) Comparative Example 8 HT-1 4.31 5.53 (0.138, 0.127)

In Table 5, the organic light emitting devices of Experimental Examples 17 to 21 using the compound of the present invention showed lower driving voltage and higher efficiency than the device using HT-1 as a hole transport layer .

While the present invention has been described in connection with the preferred embodiments (the light emitting layer and the hole transport layer) of the present invention, the present invention is not limited thereto and can be variously modified and embodied within the scope of the claims and the detailed description of the invention. And falls within the scope of the specification.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (11)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R1 is hydrogen; An aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; A heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; Or an arylamine group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group,
R2 is an aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; A heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; Or an arylamine group substituted or unsubstituted with one or two or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group,
R3 and R4 are bonded directly to each other,
Ra to Re are hydrogen,
a is 3, b is 2, and c to e are 4. [2] The compound according to claim 1, wherein the compound represented by Formula 1 is a heterocyclic compound represented by Formula 3:
(3)

In the above formula (3), the definitions of R1 and R2 are as shown in formula (1). delete The compound of claim 1, wherein the compound of formula (1) is a heterocyclic compound represented by any one of the following formulas (7) to (9)
(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the general formulas (7) to (9), R 1 and R 2 are each independently an aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; A heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group; Or an arylamine group substituted or unsubstituted with one or two or more substituents selected from the group consisting of an alkyl group, an arylamine group, an aryl group and a heterocyclic group. 2. The heterocyclic compound of claim 1, wherein at least one of R1 and R2 is selected from the group consisting of:

The compound according to claim 4, wherein R 1 or R 2 in the formulas (7) to (9) is represented by -L-Ar, L and Ar are heterocyclic compounds selected from the following Tables 1 to 3,
[Table 1]

[Table 2]

[Table 3]

A 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 comprises a heterocyclic compound according to any one of claims 1, 2, and 4 to 6, And the organic light emitting device. [Claim 7] The organic light emitting device of claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. [Claim 7] The organic light emitting diode of claim 7, wherein the organic layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound as a host material, and further includes another host material. [Claim 7] The organic light emitting diode of claim 7, wherein the organic layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound, and further comprises a dopant compound. [Claim 7] The organic light emitting device of claim 7, wherein the organic material layer comprises a hole transporting layer, and the hole transporting layer comprises the heterocyclic compound.

Images