KR20160122432A - Novel compound and light-emitting diode containing the same - Google Patents

Abstract

The present invention relates to a novel compound and a light-emitting device, wherein the light-emitting device comprises: a first electrode; an organic layer provided on the first electrode; an electron-transporting layer provided on the organic layer; and a second electrode provided on the electron-transporting layer, wherein the organic layer includes a compound represented by Chemical Formula 1 below. [Chemical Formula 1] In the Chemical Formula 1 above, Ar_1, Ar_2, Ar_3, Ar_4, L_1, L_2, L_3, L_4, L_5, m and n are as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and a light emitting device comprising the compound.

The present invention relates to a novel compound and a light emitting device comprising the same.

An organic light-emitting diode (OLED) is basically a structure in which an organic thin film including an organic light emitting layer is sandwiched between two electrodes. At least one of the two electrodes is transparent, and an appropriate voltage Is a kind of organic electronic device that utilizes the light emitted from the visible light region in the organic light emitting layer when a voltage of between 5 and 10 V is applied.

Such a light emitting device is basically a self-light emitting device in which the thickness of an actual device including an electrode is as very small as a few micrometers or less, and light directly emits from the device itself, and thus has a high response speed and a wide viewing angle as a display device. In addition, since the manufacturing process is simple, it is possible to realize a flexible device using an organic thin film, and it is possible to implement a device through a printing process from a solution state as well as a vacuum process in some cases. .

Conventionally, a light emitting device has been applied as a component to be applied to a low current / low power mobile product, but recently its application range has been gradually expanded to a high current / high output area, and accordingly, a high luminance / high reliability has been demanded. Various methods for improving the luminous efficiency of a light emitting device have been studied in accordance with this trend.

The results of the present study are as follows:

First, Patent Document 1 relates to a light emitting device including PEDOT / PSS as a hole transporting material, and the composition including the PEDOT / PSS has an intermediate ionization potential slightly higher than 4.8 eV (between the ionization potential of the anode and the ionization potential of the light emitting body ). ≪ / RTI > This occurs as the composition induces holes injected from the anode to reach the HOMO level of the organic light emitting material or the hole transporting material.

Next, Patent Document 2 relates to a composition including PEDOT / PSS, and the composition can be subjected to a solution process such as inkjet printing, thereby making it possible to more easily manufacture a device. In addition, since the composition uses an excessive amount of PSS (i.e., an amount exceeding the amount required to stabilize the charge on the PEDOT), not only can the lifetime of the light emitting device be prolonged, but also PSS can be prevented from being precipitated from the PEDOT solution have.

However, in the case of the light emitting device according to Patent Document 1, since the LUMO energy level of the PEDOT / PSS is lower than the LUMO energy level of the organic material used as the light emitting layer material, it is difficult to manufacture the light emitting device with high efficiency and long life. In the case of Patent Document 2, a composition used for a light emitting device has a strong acidity by containing an excess amount of PSS. This strong acid is formed by etching indium tin oxide (ITO) to form indium, tin, It may cause problems such as emission into the PEDOT, deterioration of the light emitting polymer, and the like.

As described above, studies for improving the luminous efficiency and the luminescent lifetime of the conventional light emitting device have been continuously carried out. However, since the compounds used in the light emitting device and the light emitting device developed so far are not effective enough to be used in high current / high power applications, there is a desperate need for a solution that can solve them.

European Patent No. 0,686,662 U.S. Patent No. 6,605,823

SUMMARY OF THE INVENTION An object of the present invention is to provide a compound capable of improving the luminescent lifetime by increasing the luminous efficiency and lowering the driving voltage of the light emitting device.

Another object of the present invention is to provide a light emitting device including the above compound and having an improved luminous efficiency and improved luminescent lifetime.

It is still another object of the present invention to provide an electronic device including the light emitting device.

In order to achieve the above object,

The present invention, in one embodiment,

There is provided a compound represented by the following formula 1:

[Chemical Formula 1]

In Formula 1,

Ar ₁ and Ar ₂ are each an aryl group having 6 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms is independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (R ₁ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms , Wherein R ₁ is an alkyl group having 1 to 4 carbon atoms,

L ₁ , L ₂ and L ₃ are each independently a single bond or an arylene group having 6 to 20 carbon atoms,

-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,

Ar ₃ is hydrogen or an aryl group having 6 to 30 carbon atoms,

Ar ₄ is an aryl group having 6 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms in Ar ₃ and Ar ₄ independently represents an alkyl group having 1 to 4 carbon atoms, Si (R ₂ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, An aryl group having 1 to 4 carbon atoms, R ₂ is an alkyl group having 1 to 4 carbon atoms,

L ₄ and L ₅ are independently a single bond or an arylene group having 6 to 20 carbon atoms,

m and n are each independently an integer of 1 to 3,

-L ₄ - (Ar ₃ ) _m and -L ₅ - (Ar ₄ ) _n are different from each other to form an asymmetric structure,

i) when L ₅ is a phenylene group, Ar ₄ is an aryl group having 6 to 12 carbon atoms,

ii) When L ₁ , L ₂ and L ₃ are single bonds, Ar ₁ and Ar ₂ are aryl groups having 6 to 14 carbon atoms.

In addition, the present invention, in one embodiment,

The first electrode

An organic layer provided on the first electrode;

A light emitting layer provided on the organic layer;

An electron transporting layer provided on the light emitting layer; And

And a second electrode provided on the electron transporting layer,

Wherein the organic layer comprises a compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , L ₁ , L ₂ , L ₃ , L ₄ , L ₅ , m and n are as defined above.

Further, in one embodiment, the present invention provides an electronic device including the light emitting element.

The light emitting device according to the present invention has an excellent light emitting efficiency and a long lifetime by forming an organic layer containing a compound represented by Chemical Formula 1 between the first electrode and the light emitting layer, It can be easily used in a device.

1 is an image showing the structure of a light emitting device manufactured in one embodiment according to the present invention.
2 is an image showing a structure of a light emitting device manufactured in another embodiment according to the present invention.
3 is an image showing the structure of a light emitting device manufactured in another embodiment according to the present invention.

While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are shown by way of example in the drawings and will herein be described in detail.

It should be understood, however, that the invention is not intended to be limited to the particular embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

In the present invention, the terms "comprising" or "having ", and the like, specify that the presence of a feature, a number, a step, an operation, an element, a component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed.

Hereinafter, the present invention will be described in detail with reference to the drawings, and the same or corresponding components are denoted by the same reference numerals regardless of the reference numerals, and a duplicate description thereof will be omitted.

In the present invention, the term "alkyl group" means a functional group derived from a saturated hydrocarbon in linear or branched form.

Examples of the "alkyl group" include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group (n butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1- dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, 2- Ethylpropyl group, an n-hexyl group, a 1-methyl-2-ethylpropyl group and a 1-ethyl-2- (1-ethyl-2-methylpropyl group), 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group (2,2-di methylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2- Methylpentyl group, 3-methylpentyl group, and the like.

The "alkyl group" may have from 1 to 20 carbon atoms, for example, from 1 to 12 carbon atoms, from 1 to 6 carbon atoms, or from 1 to 4 carbon atoms.

In the present invention, the "aryl group" means a monovalent substituent derived from an aromatic hydrocarbon.

Examples of the "aryl group" include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a chrycenyl group, a spirobifluorenyl group, a fluoranthenyl group (for example, a fluorenyl group, a perfluorenyl group, a fluorenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, , Phenanthrenyl group and the like.

The "aryl group" may have from 6 to 30 carbon atoms, for example, from 6 to 10 carbon atoms, from 6 to 14 carbon atoms, from 6 to 18 carbon atoms, or from 6 to 12 carbon atoms.

In the present invention, the "heteroaryl group" means an "aromatic heterocycle" or "heterocyclic" derived from a monocyclic or condensed ring. The "heteroaryl group" includes at least one hetero atom such as nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) Three, or four.

Examples of the "heteroaryl group" include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, ), A triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group (e.g., benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a purinyl group, an indazolyl group, a quinolyl group, An isoquinolinyl group, a quinolizinyl group, a phthalazinyl group, a naphthylidinyl group, a quinoxalinyl group, a quinazolinyl group (a quinolizinyl group), a quinolizinyl group quinazolinyl group, cinnolinyl group, pteridinyl group, An imidazotriazinyl group, an acridinyl group, a phenanthridinyl group, a carbazolyl group, a carbazolinyl group, a pyrimidinyl group, an imidazotriazinyl group, an imidazotriazinyl group, A phenanthrolinyl group, a phenazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, and the like. A nitrogen heteroaryl group; A sulfur-containing heteroaryl group including a thienyl group, a benzothienyl group, a dibenzothienyl group and the like; A furyl group, a pyranyl group, a cyclopentapyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, And an oxygen-containing heteroaryl group which may be contained.

Specific examples of the "heteroaryl group" include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, a phenothiazoyl group, An isoxazolyl group, a furazanyl group, a phenoxazinyl group, an oxazolyl group, a benzoxazolyl group, a benzothiazolyl group, An oxadiazolyl group, an oxadiazolyl group, a pyrazoloxazolyl group, an imidazothiazolyl group, a thienofuranyl group, a furopyrrolyl group, a pyridoxazinyl group (pyridoxazinyl group), and the like.

Further, the "heteroaryl group" may have from 2 to 20 carbon atoms, for example, from 3 to 19 carbon atoms, from 4 to 15 carbon atoms or from 5 to 11 carbon atoms. For example, when a heteroatom is included, the heteroaryl group may have a ring member of 5 to 21.

In the present invention, the "arylene group" may mean a divalent substituent derived from the above-mentioned aryl group.

In the present invention, "heteroarylene group" may mean a divalent substituent derived from the above-mentioned heteroaryl group.

Further, in the present invention, the heteroaryl group to which three rings are fused will be described based on the position of the carbon atom which may be substituted or substituted, based on the hetero atom, as follows.

The present invention provides a compound capable of enhancing the luminous efficiency of the light emitting device and improving the light emitting lifetime by lowering the driving voltage, and a light emitting device including the same.

The light emitting devices developed so far have problems of short emission life and low power efficiency. In order to solve such problems, various compounds have been developed as a material for a light emitting device, but there are limitations in manufacturing a light emitting device that satisfies both a light emitting lifetime and a power efficiency.

In order to solve this problem, the present invention provides a light emitting device having an organic layer comprising a compound represented by Chemical Formula 1 according to the present invention and a compound represented by Chemical Formula 1 according to the present invention between a first electrode and a light emitting layer. The light emitting device according to the present invention not only improves the luminous efficiency of the light emitting device, but also has a low driving voltage, thereby improving the light emitting lifetime by forming an organic layer between the first electrode and the light emitting layer, have. Therefore, the light emitting device according to the present invention can be usefully used in electronic devices such as a display device and a lighting device in which a light emitting device is used.

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

In one embodiment, the present invention provides a compound represented by the formula:

In Formula 1,

Ar ₁ and Ar ₂ are each an aryl group having 6 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms is independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (R ₁ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms , Wherein R ₁ is an alkyl group having 1 to 4 carbon atoms,

L ₁ , L ₂ and L ₃ are each independently a single bond or an arylene group having 6 to 20 carbon atoms,

-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,

Ar ₃ is hydrogen or an aryl group having 6 to 30 carbon atoms,

Ar ₄ is an aryl group having 6 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms in Ar ₃ and Ar ₄ independently represents an alkyl group having 1 to 4 carbon atoms, Si (R ₂ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, An aryl group having 1 to 4 carbon atoms, R ₂ is an alkyl group having 1 to 4 carbon atoms,

L ₄ and L ₅ are independently a single bond or an arylene group having 6 to 20 carbon atoms,

m and n are each independently an integer of 1 to 3,

-L ₄ - (Ar ₃ ) _m and -L ₅ - (Ar ₄ ) _n are different from each other to form an asymmetric structure,

i) when L ₅ is a phenylene group, Ar ₄ is an aryl group having 6 to 12 carbon atoms,

ii) When L ₁ , L ₂ and L ₃ are single bonds, Ar ₁ and Ar ₂ are aryl groups having 6 to 14 carbon atoms.

Specifically, the compound of formula (I) according to the present invention may be a compound represented by the following formula (1a):

<Formula 1a>

In formula (1a)

Ar ₁ and Ar ₂ are each an aryl group having 6 to 14 carbon atoms,

The C 6 -C 14 aryl group substituted with one or more substituents selected from the group consisting of alkyl, Si (R _{1) 3} and a cyano group each independently having 1 to 4 carbon atoms that has or is unsubstituted, wherein R ₁ has a carbon number Gt; is an alkyl group having 1 to 4 carbon atoms,

L ₁ , L ₂ and L ₃ are independently a single bond or an arylene group having 6 to 10 carbon atoms,

-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,

Ar ₃ is hydrogen or an aryl group having 6 to 14 carbon atoms,

Ar ₄ is an aryl group having 6 to 14 carbon atoms,

The aryl group having 6 to 14 carbon atoms of Ar ₃ and Ar ₄ is, independently of each other, unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (R ₂ ) ₃ and cyano group , R ₂ is an alkyl group having 1 to 4 carbon atoms,

L ₅ is a single bond or an arylene group having 6 to 14 carbon atoms,

m and n are each independently an integer of 1 to 3,

o is 0 or 1, wherein when o is 0, it means a single bond,

및 -L₅-(Ar₄)_n은 서로 상이하여 비대칭 구조를 형성하되,

And -L ₅ - and (Ar _{4) n} is different from each other to form a asymmetrical structure,

When L ₅ is a phenylene group, Ar ₄ is an aryl group having 6 to 12 carbon atoms.

Specifically, in Formula 1a,

Ar ₁ and Ar ₂ are each a phenyl group or a naphthyl group,

The phenyl group and a naphthyl group is an alkyl group, Si (CH _{3) 3} and a cyano group is substituted by one or more substituents selected from the group consisting of and or or unsubstituted ring having 1 to 4 carbon atoms;

L ₁ , L ₂ and L ₃ are, independently of each other, a single bond or a phenylene group;

Ar ₃ is hydrogen, a phenyl group, a naphthyl group or an anthracenyl group;

-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,

Ar ₄ is a phenyl group, a naphthyl group, or an anthracenyl group substituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ , a cyano group, a phenyl group, and a naphthyl group;

L ₅ may be a single bond, a phenylene group, a naphthylene group, or an anthracenylene group.

As an example, in the above formula (Ia) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups which are unsubstituted or substituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ and cyano group,

L ₁ , L ₂ and L ₃ are single bonds,

Ar &lt; ₃ &gt; is hydrogen,

Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group substituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ , a cyano group, a phenyl group, and a naphthyl group,

L ₅ is a single bond, a phenylene group, a naphthylene group or an anthracenylene group,

n is 1 or 2,

o can be zero.

More specifically, the compound represented by Formula 1 may have a structure represented by the following formulas a-1 to a-17:

&Lt; Formula (a-1)

<Formula a-2>

<Formula a-3>

<Chemical Formula a-4>

&Lt; Formula (a-5)

<Formula a-6>

<Formula a-7>

<Formula a-8>

<Formula a-9>

<Formula a-10>

<Formula a-11>

<Formula a-12>

<Formula a-13>

<Formula a-14>

<Formula a-15>

<Formula a-16>

.
<Formula a-17>

.

As another example, in the formula (Ia) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups,

Ar ₃ is hydrogen or a phenyl group,

Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group,

L ₁ to L ₃ , and L ₅ are single bonds,

m is 1 or 2,

o can be 0 or 1.

Specifically, the compound represented by the formula (1) may have a structure represented by the following formulas (b-1) to (b-11)

<Formula b-1>

<Formula b-2>

<Formula b-3>

<Formula b-4>

<Formula b-5>

<Formula b-6>

<Formula b-7>

<Formula b-8>

<Formula b-9>

<Formula b-10>

.
<Formula b-11>

.

As another example, in the formula (1a) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups,

Ar ₃ is hydrogen or a phenyl group,

Ar ₄ is a phenyl group or a naphthyl group,

L ₁ , L ₂ and L ₃ are single bonds,

L ₅ is a phenylene group, a naphthylene group or an anthracenylene group,

m is 1 or 2,

n is 1,

o can be 0 or 1.

Specifically, the compound represented by Formula 1 may have a structure represented by the following formulas c-1 to c-13:

&Lt; Formula c-1 >

&Lt; Formula c-2 >

<Formula c-3>

<Formula c-4>

<Formula c-5>

<Formula c-6>

<Formula c-7>

<Formula c-8>

<Formula c-9>

<Formula c-10>

&Lt; Formula c-11 &

<Formula c-12>

.
<Formula c-13>

.

As an example, in the above formula (Ia) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups,

Ar &lt; ₃ &gt; is hydrogen,

Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group substituted or unsubstituted with Si (CH ₃ ) ₃ , a cyano group or a phenyl group,

L ₁ and L ₂ are single bonds,

L ₃ is a phenylene group,

L ₅ is a single bond, a phenylene group, a naphthylene group or an anthracenylene group,

n is 1 or 2,

o can be zero.

Specifically, the compound represented by Formula 1 may have a structure represented by the following Formulas d-1 to d-10:

<Formula d-1>

<Formula d-2>

<Formula d-3>

<Formula d-4>

<Formula d-5>

<Formula d-6>

<Formula d-7>

<Formula d-8>

<Formula d-9>

.
<Formula d-10>

.

As another example, in the formula (Ia) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups,

Ar ₃ is hydrogen or a phenyl group,

Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group,

L ₁ , L ₂ and L ₅ are single bonds,

L ₃ is a phenylene group,

m is 1 or 2,

o can be 0 or 1.

Specifically, the compound represented by Formula 1 may have a structure represented by the following formulas e-1 to e-11:

&Lt; Formula e-1 >

&Lt; Formula e-2 >

<Formula (e-3)>

<Formula (e-4)>

&Lt; Formula e-5 >

&Lt; Formula e-6 >

&Lt; Formula e-7 >

<Formula e-8>

&Lt; Formula e-9 >

&Lt; Formula e-10 >

.
&Lt; Formula e-11 >

.

As another example, in the formula (1a) according to the present invention,

Ar ₁ and Ar ₂ are phenyl groups,

Ar ₃ is hydrogen or a phenyl group,

Ar ₄ is a phenyl group or a naphthyl group,

L ₁ and L ₂ are single bonds,

L ₃ is a phenylene group,

L ₅ is a phenylene group, a naphthylene group or an anthracenylene group,

m is 1 or 2,

n is 1,

o can be 0 or 1.

Specifically, the compound represented by the formula (1) may have a structure represented by the following formulas (f-1) to (f-14)

<Formula f-1>

<Formula f-2>

<Formula f-3>

<Formula f-4>

<Formula f-5>

<Formula f-6>

<Formula f-7>

<Formula f-8>

<Formula f-9>

<Formula f-10>

<Formula f-11>

<Formula f-12>

<Formula f-13>

.
<Formula f-14>

.

In addition, the present invention, in one embodiment,

A first electrode;

An organic layer provided on the first electrode;

A light emitting layer provided on the organic layer;

An electron transporting layer provided on the light emitting layer; And

And a second electrode provided on the electron transporting layer,

Wherein the organic layer comprises a compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , L ₁ , L ₂ , L ₃ , L ₄ , L ₅ , m and n are as defined above.

Recently, the application range of the light emitting device has been expanded to the high current / high output field, so that the light emitting efficiency and luminous lifetime of the light emitting device have been demanded. At this time, the light emitting efficiency and the light emitting lifetime can be improved by satisfactorily combining holes and electrons in the light emitting layer. However, electrons injected from the second electrode may overflow to the hole transporting layer through the light emitting layer, thereby reducing the coupling efficiency of holes and electrons in the light emitting layer. Therefore, in order to efficiently bond the holes and electrons in the light emitting layer, it is necessary to prevent electrons injected from the second electrode from being separated from the light emitting layer while preventing excitons formed in the light emitting layer from diffusing or being separated .

In order to overcome such a problem, the light emitting device according to the present invention may have a structure including an organic layer including a compound represented by Chemical Formula 1 between the first electrode and the light emitting layer. The organic layer according to the present invention can prevent the electrons injected from the second electrode from flowing into the hole transporting layer via the light emitting layer or the excitons formed in the light emitting layer diffusing in the direction of the first electrode to prevent non-emission disappearance. In addition, it is possible to prevent non-emission disappearance of the excitons formed in the light emitting layer through an "exciton dissociation" process at the interface between the light emitting layer and the hole transporting layer. That is, the organic layer can prevent the electrons and excitons from escaping from the light emitting layer, thereby adjusting the charge balance in the light emitting layer, thereby maximizing the excitation efficiency and the light emission extinction in the light emitting layer. , The driving voltage may be lowered and the luminescent lifetime may be improved.

1 to 3 are schematic cross-sectional views of a light emitting device according to the present invention.

The light emitting devices 100 to 100B according to the present invention include a first electrode 105, an organic layer 104, a light emitting layer 103, an electron transporting layer 102, and a second electrode 101 on a base substrate 106 And may have a sequentially stacked structure.

Hereinafter, each component of the light emitting device according to the present invention will be described in detail with reference to FIGS. 1 to 3. FIG.

The first electrode 105 is a conductive material and is formed on the base substrate 106 to function as an anode of the light emitting devices 100 to 100B. .

At this time, the first electrode 105 may be a transparent electrode or an opaque (reflective) electrode. When the first electrode 105 is a transparent electrode, the first electrode 105 may include indium tin oxide (ITO), tin oxide (SnO ₂ ), or the like. Also, in the case of an opaque (reflective) electrode, the first electrode 105 may comprise an ITO / silver (Ag) / ITO structure.

Next, in the light emitting devices 100 to 100B according to the present invention, the organic layer 104 is located between the first electrode 105 and the light emitting layer 103, and may have a single layer or a multi-layer structure of two or more layers.

Specifically, the organic layer 104 according to the present invention has a single-layer structure as shown in Fig. 1, or has a first organic layer 107, a second organic layer 108, , A third organic layer 109, and the like.

In the organic layer 104, an organic layer formed at a position in contact with the light emitting layer 103, that is, an organic layer 104 having a single layer structure shown in FIG. 1; Or the first organic layer 107 included in the organic layer 104 of the multi-layer structure shown in FIG. 2 and FIG. 3 is formed at a position in contact with the light emitting layer 103 including the compound represented by the formula 1 according to the present invention, An electron blocking layer (EBL); Exciton barrier layer; Or an exciton dissociation blocking layer (EDBL).

An extra organic layer (hereinafter referred to as a second organic layer 108) such as a second organic layer 108 and a third organic layer 109 excluding the first organic layer 107 in the organic layer 104, which is not in contact with the light emitting layer 103, Quot; extra organic layer ") may be positioned between the first organic layer 107 and the first electrode 105 and function as a hole transport layer and / or a hole injection layer.

Referring to FIG. 3, the second organic layer 108, which does not contact the light emitting layer 103, may serve as a hole transport layer. The second organic layer 108 may include, for example, 4,4-bis [N- (1-naphthyl) -N-phenylamine] biphenyl (N-NPD) N, N-bis (3-methylphenyl) -1,1-biphenyl-4,4-diamine (TPD) and poly- (N-vinylcarbazole) (PVCz) . The third organic layer 109 not in contact with the light emitting layer 103 may serve as a hole injecting layer. At this time, the first electrode 105 and the second organic layer 108 are stacked, and may include, for example, copper phthalocyanine (CuPc). However, the present invention is not limited thereto.

In addition, the extra organic layer may include a compound represented by the following formula (3) as a hole-transporting compound. More specifically, for example, in the case of the light emitting device 100B in which the third organic layer 109, the second organic layer 108, and the first organic layer 107 are sequentially stacked on the first electrode 105, The first organic layer 107 in contact with the light emitting layer 103 includes a compound represented by the formula 1 as described above and at least one of the second organic layer 108 and the third organic layer 109, (3): &lt; EMI ID =

In Formula 3,

R ₄ and R ₆ are each independently an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 30 carbon atoms,

R ₅ is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 4 to 20 carbon atoms,

When R ₅ is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 4 to 20 carbon atoms, the aryl group and the heteroaryl group are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms Substituted or unsubstituted.

Specifically, in Formula 3 according to the present invention,

R ₄ is an alkyl group having 1 to 6 carbon atoms or a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group; Naphthyl group; Or a phenanthryl group,

R ₆ may be a methyl group, an ethyl group or a phenyl group.

More specifically, the compound represented by Formula 3 may be a compound having a structure represented by Formula 3a:

[Chemical Formula 3]

.

.

Further, in the organic layer 104 according to the present invention, any one of the extra organic layers not in contact with the light emitting layer 103 may further include at least one P-type dopant.

More specifically, for example, an organic layer 104 having a multilayer structure in which a third organic layer 109, a second organic layer 108, and a first organic layer 107 are sequentially stacked on the first electrode 105 The first organic layer 107 in contact with the light emitting layer 103 includes the compound of the first chemical formula 1 as described above and the second organic layer 108 and the third organic layer 108 which do not contact the light emitting layer 103, At least one of the organic layers 109 may include a compound represented by Formula 3, and any one of the second organic layer 108 and the third organic layer 109 may further include at least one P-type dopant.

At this time, the P-type dopant may include at least one P-type organic material dopant or P-type inorganic material dopant, and may include at least one P-type organic material dopant and at least one P-type inorganic material dopant at the same time.

As the P-type organic dopant, for example, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanoantho-2,6-quinodimethane (11,11,12,12 2,6-quinodimethane, TNAP), 3,6-difluoro-2,5-dihydroxy-2,5,7,7,8,8-hexacyano-quinodimethane, Tetracyanoquinodimethane (TCNQ), etc., and may include any one or more of compounds represented by the following formulas (4) to (8) You may:

In the general formulas (7) and (8)

R ₇ is a cyano group, a sulfonic group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group,

s and t are independently of each other an integer of 1 to 5;

Y ₁ and Y ₂ are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,

The aryl group and the heteroaryl group are each independently substituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a hydroxyl group, and a halogen group Or not.

More specifically, the compound represented by the formula (8) may be a compound represented by the following formula (8a) or (8b):

[Chemical Formula 8a]

[Formula 8b]

.

.

Examples of the P-type inorganic material dopant include metal oxides, metal halides, and the like. Specifically, it may include MoO ₃ , V ₂ O ₅ , WO ₃ , SnO ₂ , ZnO, MnO ₂ , CoO ₂ , ReO ₃ , TiO _2, FeCl ₃ , SbCl ₅ , MgF ₂ , Or a mixture of two or more thereof.

Further, the content of the P-type dopant may be about 0.5 parts by weight to about 20 parts by weight, or about 0.5 parts by weight to about 5 parts by weight based on 100 parts by weight of the hole transporting compound. Or about 100 parts by weight of the hole-transporting compound, about 1 part by weight to 10 parts by weight; 1 part by weight to 5 parts by weight; 1.5 to 6 parts by weight; Or 2 parts by weight to 5 parts by weight.

When the content of the P-type dopant is about 0.5 parts by weight to about 20 parts by weight based on 100 parts by weight of the hole transporting compound, the P-type dopant prevents excessive leakage current without deteriorating the physical properties of the hole transporting compound . In addition, the P-type dopant can reduce the energy barrier at the interfaces with the upper and lower layers in contact with the third organic layer 109.

In the light emitting devices 100 to 100B according to the present invention, the organic layer 104 can increase the luminous efficiency by adjusting the thickness according to the resonant length of the light emitting devices 100 to 100B, And not at the interface between the light-emitting layer 103 and the other layer, so that the thickness of the light-emitting layer 103 is not particularly limited.

Specifically, when the structure of the organic layer 104 is a single layer, it may have a thickness ranging from 5 A to 2,000 A, and in the case of a multi-layer structure having two or more layers, each individual layer has a thickness ranging from 5 A to 1,000 A .

The light emitting layer 103 is located between the organic layer 104 and the second electrode 101 and the wavelength of the light emitted by the light emitting layer 103 is May be different depending on the kind of the compound forming the light emitting layer 103. At this time, the compound forming the light emitting layer 103 is not particularly limited as long as it is generally used in the art, and can be commercially obtained or used.

Next, in the light emitting devices 100 to 100B according to the present invention, the electron transporting layer 102 is disposed between the light emitting layer 103 and the second electrode 101, and includes an electron transporting layer (ETL) / RTI &gt; and / or an electron injecting layer (EIL) (not shown). At this time, the electron transporting layer may include a compound represented by the following formula (2)

In Formula 2,

Z ₁ to Z ₃ independently represent hydrogen, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, An alkoxy group or a diarylphosphine oxide group having 6 to 20 carbon atoms,

When Z ₁ to Z ₃ independently represent an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, or a diarylphosphine oxide group having 6 to 20 carbon atoms, the aryl group, the heteroaryl group And the diarylphosphine oxide group is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a diarylphosphine oxide group having 6 to 20 carbon atoms,

p and q are each independently an integer of 1 to 3;

Specifically, the compound represented by Formula 2 may be a compound represented by Formula 2a:

(2a)

In the above formula (2a)

Ar ₅ is hydrogen, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, an imidazolyl group, a benzothienyl group, a benzoxazolyl group, or a diarylphosphine oxide group,

Z ₂ and Z ₃ independently represent hydrogen, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group,

p and q are independently from each other 1 to 3;

More specifically, the compound represented by formula (2a) may be selected from the following formulas (2a-1) to (2a-7)

<Formula 2a-1>

&Lt; Formula 2a-2 >

&Lt; Formula 2a-3 >

&Lt; Formula 2a-4 >

<Formula 2a-5>

&Lt; Formula 2a-6 >

.
<Formula 2a-7>

.

In addition, the light emitting devices 100 to 100B according to the present invention may further include an organic layer (not shown) positioned between the light emitting layer 103 and the second electrode 101.

The organic layer is disposed between the light emitting layer 103 and the second electrode 101, specifically between the light emitting layer 103 and the electron transporting layer 102 so that holes are emitted from the first electrode 105 to the light emitting layer 103 Transporting layer 102 to prevent the electron transporting layer 102 from being introduced into the electron transporting layer 102. The organic layer may serve as an exciton blocking layer for preventing the excitons formed in the light emitting layer 103 from diffusing toward the second electrode 101 to prevent the excitons from disappearing due to non-emission have.

At this time, the organic layer can increase the luminous efficiency by controlling the thickness according to the resonance length of the light emitting devices 100 to 100B, and the exciton can be formed on the light emitting layer 103, not the interface between the light emitting layer 103 and the other layers. As shown in FIG.

The second electrode 101 is a conductive material and is positioned on the light emitting layer 103 to serve as a cathode of the light emitting devices 100 to 100B .

The second electrode 101 may include a metal such as nickel, magnesium, calcium, silver, aluminum, and indium, or an alloy including two or more of the metals. More specifically, the second electrode 101 may include aluminum . In addition, the second electrode 101 may have a single-layer structure or a multi-layer structure of two or more layers. In addition, when the first electrode 105 is an opaque electrode, the second electrode 101 may be a transparent or translucent electrode. In this case, the second electrode 101 may be an alloy containing magnesium and silver. , And may have a thickness of 100 ANGSTROM to 150 ANGSTROM.

In addition, in the light emitting devices 100 to 100B according to the present invention, the first electrode 105, the organic layer 104, the light emitting layer 103, the electron transporting layer 102, the second electrode 101, The deposition method may be used. However, the deposition method is not limited as long as it is a method commonly used in the art besides the deposition method.

Furthermore, the present invention provides, in one embodiment, an electronic device including the light emitting element described above. At this time, the electronic device according to the present invention may be a display device or a lighting device, but is not limited thereto.

The electronic device according to the present invention includes a light emitting device in which the luminous efficiency is increased and the luminescent lifetime is improved by introducing an organic layer containing the compound represented by the general formula (1) between the first electrode and the light emitting layer, It can also be used in high current / high power fields.

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples.

However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the present invention is not limited to the following Examples and Experimental Examples.

Example  One.

(20.0 g, 64.7 mmol), the formula C (38.97 g, 71.2 mmol) was added to a 500 mL three-necked round bottom flask with nitrogen and then o-xylene (200 mL) , palladium acetate _{(Pd (OAc) 2, 290} mg, 1.29 mmol), sodium tert- butoxide (NaO t-Bu, 7.5 g , 77.6 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.7 mL) was added thereto, followed by stirring at 130 DEG C for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 30 minutes, and filtered to obtain the objective compound (formula 1A, 35.1 g, 70%) as a light-colored solid.

MALDI-TOF: m / z = 775.3255 (C ₆₀ H ₄₁ N = 775.32).

Example  2.

(15.0 g, 48.5 mmol), Formula D (21.1 g, 53.4 mmol), and N, N'-dicyclohexylcarbodiimide were placed in a 500 mL 3-neck round bottom flask, P (t-Bu) ₃ , 1.3 (1-tert-butylphenyl) palladium acetate (Pd (OAc) ₂ , 218 mg, 0.97 mmol), sodium tert- mL), and the mixture was stirred at 130 캜 for 9 hours. Thereafter, the reaction mixture was cooled to room temperature, poured into methanol (2,000 mL), stirred for 20 minutes, and filtered to obtain the target compound (Formula 1B, 22.7 g, 75%) as a gray solid.

MALDI-TOF: m / z = 623.2645 (C ₄₈ H ₃₃ N = 623.26).

Example  3.

(10.0 g, 32.3 mmol), E (14.1 g, 35.6 mmol) was added to a 500 mL three-neck round bottom flask with nitrogen and then o-xylene (150 mL) , palladium acetate _{(Pd (OAc) 2, 145} mg, 0.65 mmol), sodium tert- butoxide (NaO t-Bu, 3.7 g , 38.8 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 0.9 mL), and the mixture was stirred at 130 캜 for 11 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (1,500 mL), stirred for 30 minutes, and filtered to obtain the objective compound (1C, 16.1, 80%) as a gray solid.

MALDI-TOF: m / z = 623.2634 (C ₄₈ H ₃₃ N = 623.26).

Example  4.

(15.0 g, 38.9 mmol), E (16.9 g, 42.8 mmol) in a 500 mL three-necked round bottom flask was charged with nitrogen and then o-xylene (200 mL) , palladium acetate _{(Pd (OAc) 2, 175} mg, 0.78 mmol), sodium tert- butoxide (NaO t-Bu, 4.49 g , 46.7 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.1 mL) was added thereto, followed by stirring at 130 ° C for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 20 minutes, and filtered to obtain the aimed compound as a gray solid (1D, 22.6 g, 83%).

MALDI-TOF: m / z = 699.2933 (C ₅₄ H ₃₇ N = 699.29).

Example  5.

(20.0 g, 64.7 mmol), Formula F (22.7 g, 71.2 mmol), and N, N-dimethylacetamide were placed in a 500 mL three- , palladium acetate _{(Pd (OAc) 2, 290} mg, 1.29 mmol), sodium tert- butoxide (NaO t-Bu, 7.5 g , 77.6 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.7 mL) was added thereto, followed by stirring at 130 DEG C for 6 hours. Thereafter, the reaction mixture was cooled to room temperature, poured into methanol (2,000 mL), stirred for 30 minutes, and filtered to obtain the target compound as a light gray solid (Formula 1E, 28.3 g, 80%).

MALDI-TOF: m / z = 547.2298 (C ₄₂ H ₂₉ N = 547.23).

Example  6.

(15.0 g, 48.5 mmol), the compound G (34.6 g, 53.4 mmol), and a solution of the compound of the formula (III) in a 500 mL three-necked round bottom flask were charged with nitrogen and then o- , palladium acetate _{(Pd (OAc) 2, 218} mg, 0.97 mmol), sodium tert- butoxide (NaO t-Bu, 5.59 g , 58.2 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.3 mL) was added thereto, followed by stirring at 130 DEG C for 7 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 20 minutes, and filtered to obtain the objective compound (1F, 36.5 g, 86%) as a light gray solid.

MALDI-TOF: m / z = 875.3542 (C ₆₈ H ₄₅ N = 875.36).

Example  7.

(10.0 g, 25.9 mmol), the formula H (12 g, 28.5 mmol) was added to a 500 mL three-neck round bottom flask with nitrogen and then o-xylene (200 mL) Bu, 3 g, 31.1 mmol) and tri-tert-butylphosphine (P (t-Bu)) ₃ , palladium acetate (Pd (OAc) ₂ , 120 mg, 0.52 mmol), sodium tert- 0.7 mL), and the mixture was stirred at 130 ° C for 11 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (1,500 mL), stirred for 20 minutes, and filtered to obtain the objective compound (1G, 14.1 g, 75%) as a light gray solid.

MALDI-TOF: m / z = 723.2889 (C ₅₆ H ₃₇ N = 723.29).

Example  8.

(15.0 g, 40 mmol), Formula I (25.6 g, 42.8 mmol) was added to a 500 mL three-necked round bottom flask with nitrogen and then o-xylene (200 mL) , palladium acetate _{(Pd (OAc) 2, 175} mg, 0.78 mmol), sodium tert- butoxide (NaO t-Bu, 4.49 g , 46.7 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.1 mL) was added thereto, followed by stirring at 130 ° C for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 20 minutes, and filtered to obtain the target compound (1H, 27.4 g, 78%) as a gray solid.

MALDI-TOF: m / z = 901.3784 (C ₇₀ H ₄₇ N = 901.37).

Example  9.

(20.0 g, 51.9 mmol), the formula J (39.85 g, 57.1 mmol), and a solution of the compound of the formula (2) in a 500 mL three-neck round bottom flask were charged with nitrogen and then o- , palladium acetate _{(Pd (OAc) 2, 233} mg, 1.04 mmol), sodium tert- butoxide (NaO t-Bu, 5.99 g , 62.3 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 1.4 mL), and the mixture was stirred at 130 캜 for 9 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 30 minutes, and filtered to obtain the aimed compound as a gray solid (Formula I, 39.0 g, 75%).

MALDI-TOF: m / z = 1001.4011 (C ₇₈ H ₅₁ N = 1001.40).

Example  10.

(15.0 g, 48.5 mmol) and K (13 g, 53.4 mmol) were charged in a 500 mL three-neck round bottom flask with nitrogen and then o-xylene (200 mL) , palladium acetate _{(Pd (OAc) 2, 218} mg, 0.97 mmol), sodium tert- butoxide (NaO t-Bu, 5.59 g , 58.2 mmol) and tri tert- butylphosphine _{(P (t-Bu) 3} , 0.7 mL), and the mixture was stirred at 130 ° C for 12 hours. Thereafter, the reaction mixture was cooled to room temperature, charged into methanol (2,000 mL), stirred for 30 minutes, and filtered to obtain the objective compound (IJ, 19.4 g, 85%) as a light gray solid.

MALDI-TOF: m / z = 471.2024 (C ₃₆ H ₂₅ N = 471.20).

Example  11 - 20. Fabrication of Light Emitting Device

A compound represented by the following formula (9) as a host material was deposited at a rate of 1 Å / sec on a first electrode formed of indium tin oxide (ITO), and a P-type dopant (HAT-CN ) Was co-evaporated at a ratio of 3 parts by weight with respect to 100 parts by weight of the host material to form a 100 Å-thick third organic layer. A compound represented by Chemical Formula 9 was deposited on the third organic layer to a thickness of 300 ANGSTROM to form a second organic layer.

As shown in the following Table 1, the compounds prepared in Examples 1 to 10 were deposited on the second organic layer to a thickness of 100 Å, respectively, to form a first organic layer.

On the first organic layer, a compound represented by the following formula (11) and a compound represented by the following formula (12) were co-deposited at a weight ratio of 100: 5 to form a 200 Å thick emitting layer.

Next, a compound represented by the following formula (13) and a compound represented by the following formula (14) were co-deposited on the light emitting layer at a weight ratio of 50:50 to form a 360 Å thick electron transport layer. Next, a 5 Å thick electron injecting layer was formed on the electron transporting layer using a compound represented by the following formula (14).

Finally, a second electrode was formed on the electron injecting layer with an aluminum thin film having a thickness of 1,000 A to prepare a light emitting device.

The first organic layer Example 11 The compound of formula 1A prepared in example 1 Example 12 The compound of the formula 1B prepared in Example 2 Example 13 The compound of formula 1C prepared in Example 3 Example 14 The compound of the formula 1D prepared in Example 4 Example 15 The compound of the formula 1E prepared in Example 5 Example 16 Compound of Formula 1F prepared in Example 6 Example 17 The compound of the formula 1G prepared in Example 7 Example 18 The compound of formula (1H) prepared in example 8 Example 19 The compound of formula (I) prepared in Example 9 Example 20 The compound of the formula 1J prepared in Example 10

Comparative Example  One.

A light emitting device not including the first organic layer was fabricated in the same manner as in Example 11 except that the light emitting layer was formed without forming the first organic layer on the second organic layer.

Comparative Example  2.

In Example 11, except that the first organic layer was formed using the compound represented by the following formula (15) instead of forming the first organic layer using the compound (1A) prepared in Example 1, 11 to prepare a light emitting device including a first organic layer having a single-layer structure.

Comparative Example  3.

In Example 11, except that the first organic layer was formed using the compound represented by the following formula (16) instead of forming the first organic layer using the compound (1A) prepared in Example 1, 11 to prepare a light emitting device including a first organic layer having a single-layer structure.

Comparative Example  4.

In Example 11, except that the first organic layer was formed using the compound represented by Formula 17 instead of forming the first organic layer using the compound (Formula 1A) prepared in Example 1, 11 to prepare a light emitting device including a first organic layer having a single-layer structure.

Experimental Example  1. Evaluation of luminescence efficiency and luminescence lifetime of a light emitting device

In order to evaluate the luminous efficiency and the luminescence lifetime of the light emitting device containing the compound represented by the formula (1) in the first organic layer according to the present invention, the following experiment was conducted.

First, a UV curing sealant was dispensed on the edge of a cover glass having a moisture absorbent (Getter) attached thereto in a glove box in a nitrogen atmosphere. Then, the light emitting devices prepared in Examples 11 to 20 and Comparative Examples 1 to 4 The cover glass was cemented. Thereafter, the cured light emitting device was irradiated with UV light to be cured, and the light emitting efficiency of the cured light emitting device was measured. At this time, the luminous efficiency was measured based on the value when the luminance was 1,000 cd / m ² , and the unit of the measured value was lm / W.

Next, the lifetime of each of the light emitting devices manufactured in Examples 11 to 20 and Comparative Examples 1 to 4 was measured using a lifetime measuring device provided in a measuring oven kept constant at a temperature of 25 캜. In this case, T ₅₀ represents the time taken for the luminance of the light emitting device to reach 50% of the initial luminance when the initial luminance of the light emitting device is 5,000 cd / m ² . The value for the lifetime can be converted to the expected lifetime if measured on other measurement conditions based on the conversion formula known to the skilled person. The measured results are shown in Table 2 below.

Luminous efficiency
[lm / W] Luminescent lifetime
(T ₅₀ [hr])
Luminous efficiency
[lm / W] Luminescent lifetime
(T ₅₀ [hr]) Example 11 9.5 383 Example 18 7.4 287 Example 12 9.3 377 Example 19 8.7 358 Example 13 8.5 338 Example 20 8.2 321 Example 14 7.2 274 Comparative Example 1 4.1 132 Example 15 7.5 291 Comparative Example 2 6.4 253 Example 16 9.2 374 Comparative Example 3 6.3 241 Example 17 6.4 268 Comparative Example 4 4.5 173

As shown in Table 2, it can be seen that the light emitting device according to the present invention has excellent luminous efficiency and light emission lifetime.

More specifically, with reference to Table 2, the light emitting device including the compound represented by Formula 1 according to the present invention in the first organic layer has an emission efficiency of 6.4 to 9.5 lm / W and a luminescence lifetime of 268 to 383 hours.

On the other hand, in the case of the light emitting device not including the first organic layer (Comparative Example 1), the luminous efficiency was 4.1 lm / W and the luminescent lifetime was 132 hours, Respectively. In addition, even in the case of the light emitting device including the first organic layer and not including the compound represented by the formula (Comparative Example 2), the luminous efficiency and the luminescent lifetime were 6.4 lm / W and 253 hours, respectively, Low. In particular, in the case of the light-emitting devices (Comparative Examples 3 and 4) in which the first organic layer contains a compound having a heteroaryl group-substituted structure in which the phenylene introduced into the nitrogen atom of the carbazole has an asymmetric structure or a symmetric structure, , And the compound having a structure similar to that of Formula 1 was contained in the first organic layer, the luminescence efficiencies were 6.3 and 4.5 lm / W, respectively, and the luminescence lifetimes were 241 and 173 hours.

That is, the light emitting device having the compound represented by Formula 1 according to the present invention in the first organic layer has a luminous efficiency increased by about 1.56 to 2.32 times as compared with the light emitting device not including the first organic layer (Comparative Example 1) The lifetime is improved by about 2.03 to 2.90 times. In addition, the luminous efficiency of the luminous means is increased up to about 1.48 times as compared with the luminous means (Comparative Example 2) comprising a compound having a structure different from that of the luminous means according to the present invention even if the first organic layer is provided, It can be seen that the improvement is about 1.06 to 1.51 times.

Further, in the case of the light-emitting device (Example 11) in which the compound of Formula 1 prepared in Example 1 is included in the first organic layer, the compound of Formula 16 having a similar structure is included in the first organic layer The light emitting efficiency and the light emission lifetime were improved by about 1.51 times and 1.59 times, respectively, as compared with the device of Comparative Example 3 (Comparative Example 3). In addition, the light-emitting device (Example 12) including the compound prepared in Example 2 in the first organic layer is a device of the light-emitting device (Comparative Example 4) including the compound of Formula 17 having the similar structure in the first organic layer The luminous efficiency and the luminescence lifetime were improved by about 2.07 times and 2.18 times, respectively.

From these results, the light emitting device according to the present invention has a structure in which the first organic layer located between the first electrode and the light emitting layer is represented by Formula 1 having a structural characteristic in which a phenylene group having a symmetric structure is introduced into the nitrogen atom of the carbazole having an asymmetric structure It can be seen that the compound of the present invention has an effect of significantly improving the luminous efficiency and the luminescent lifetime in comparison with the light emitting device which does not include the first organic layer or does not contain the compound of the general formula (1)

Therefore, the light emitting device according to the present invention is excellent in improving the luminous efficiency and lifetime of the light emitting device, and thus can be usefully used in electronic devices in high current / high output fields requiring high luminance / high reliability.

100, 100A and 100B: Light emitting element
101: second electrode 102: electron transporting layer
103: light emitting layer 104: organic layer
105: first electrode 106: base substrate
107: first organic layer 108: second organic layer
109: Third organic layer

Claims (29)

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

In Formula 1,
Ar ₁ and Ar ₂ are each an aryl group having 6 to 30 carbon atoms,
The aryl group having 6 to 30 carbon atoms is independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (R ₁ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms , Wherein R ₁ is an alkyl group having 1 to 4 carbon atoms,
L ₁ , L ₂ and L ₃ are each independently a single bond or an arylene group having 6 to 20 carbon atoms,
-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,
Ar ₃ is hydrogen or an aryl group having 6 to 30 carbon atoms,
Ar ₄ is an aryl group having 6 to 30 carbon atoms,
The aryl group having 6 to 30 carbon atoms in Ar ₃ and Ar ₄ independently represents an alkyl group having 1 to 4 carbon atoms, Si (R ₂ ) ₃ , a cyano group, a haloalkyl group having 1 to 6 carbon atoms, An aryl group having 1 to 4 carbon atoms, R ₂ is an alkyl group having 1 to 4 carbon atoms,
L ₄ and L ₅ are independently a single bond or an arylene group having 6 to 20 carbon atoms,
m and n are each independently an integer of 1 to 3,
-L ₄ - (Ar ₃ ) _m and -L ₅ - (Ar ₄ ) _n are different from each other to form an asymmetric structure,
i) when L ₅ is a phenylene group, Ar ₄ is an aryl group having 6 to 12 carbon atoms,
ii) When L ₁ , L ₂ and L ₃ are single bonds, Ar ₁ and Ar ₂ are aryl groups having 6 to 14 carbon atoms.
The method according to claim 1,
A compound represented by the formula (1) is a compound represented by the following formula (1a):
<Formula 1a>

In formula (1a)
Ar ₁ and Ar ₂ are each an aryl group having 6 to 14 carbon atoms,
The C 6 -C 14 aryl group substituted with one or more substituents selected from the group consisting of alkyl, Si (R _{1) 3} and a cyano group each independently having 1 to 4 carbon atoms that has or is unsubstituted, wherein R ₁ has a carbon number Gt; is an alkyl group having 1 to 4 carbon atoms,
L ₁ , L ₂ and L ₃ are independently a single bond or an arylene group having 6 to 10 carbon atoms,
-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,
Ar ₃ is hydrogen or an aryl group having 6 to 14 carbon atoms,
Ar ₄ is an aryl group having 6 to 14 carbon atoms,
The aryl group having 6 to 14 carbon atoms of Ar ₃ and Ar ₄ is, independently of each other, unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (R ₂ ) ₃ and cyano group , R ₂ is an alkyl group having 1 to 4 carbon atoms,
L ₅ is a single bond or an arylene group having 6 to 14 carbon atoms,
m and n are each independently an integer of 1 to 3,
o is 0 or 1, and when o is 0, it means a single bond,

And -L ₅ - and (Ar _{4) n} is different from each other to form a asymmetrical structure,
When L ₅ is a phenylene group, Ar ₄ is an aryl group having 6 to 12 carbon atoms.
3. The method of claim 2,
Ar ₁ and Ar ₂ are each a phenyl group or a naphthyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, Si (CH ₃ ) ₃ and cyano group,
L ₁ , L ₂ and L ₃ are independently a single bond or a phenylene group,
Ar ₃ is hydrogen, a phenyl group, a naphthyl group or an anthracenyl group,
-L ₁ -Ar ₁ and -L ₂ -Ar ₂ are identical to each other to form a symmetrical structure,
Ar ₄ is a phenyl group, a naphthyl group, or an anthracenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ , cyano group, phenyl group, and naphthyl group,
L ₅ is a single bond, a phenylene group, a naphthylene group, or an anthracenylene group.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups which are unsubstituted or substituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ and cyano group,
L ₁ , L ₂ and L ₃ are single bonds,
Ar &lt; ₃ &gt; is hydrogen,
Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group substituted with at least one substituent selected from the group consisting of Si (CH ₃ ) ₃ , a cyano group, a phenyl group, and a naphthyl group,
L ₅ is a single bond, a phenylene group, a naphthylene group or an anthracenylene group,
n is 1 or 2,
o is 0.
5. The method of claim 4,
1. A compound having the structure of the following formulas a-1 to a-17:
&Lt; Formula (a-1)

<Formula a-2>

<Formula a-3>

<Chemical Formula a-4>

&Lt; Formula (a-5)

<Formula a-6>

<Formula a-7>

<Formula a-8>

<Formula a-9>

<Formula a-10>

<Formula a-11>

<Formula a-12>

<Formula a-13>

<Formula a-14>

<Formula a-15>

<Formula a-16>
<Formula a-17>

.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups,
Ar ₃ is hydrogen or a phenyl group,
Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group,
L ₁ to L ₃ , and L ₅ are single bonds,
m is 1 or 2,
o is 0 or 1.
The method according to claim 6,
A compound represented by the following formulas (b-1) to (b-11):
<Formula b-1>

<Formula b-2>

<Formula b-3>

<Formula b-4>

<Formula b-5>

<Formula b-6>

<Formula b-7>

<Formula b-8>

<Formula b-9>

<Formula b-10>

<Formula b-11>

.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups,
Ar ₃ is hydrogen or a phenyl group,
Ar ₄ is a phenyl group or a naphthyl group,
L ₁ , L ₂ and L ₃ are single bonds,
L ₅ is a phenylene group, a naphthylene group or an anthracenylene group,
m is 1 or 2,
n is 1,
o is 0 or 1;
9. The method of claim 8,
A compound having the structure of the following formulas c-1 to c-13:
&Lt; Formula c-1 >

&Lt; Formula c-2 >

<Formula c-3>

<Formula c-4>

<Formula c-5>

<Formula c-6>

<Formula c-7>

<Formula c-8>

<Formula c-9>

<Formula c-10>

&Lt; Formula c-11 &

<Formula c-12>

<Formula c-13>

.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups,
Ar &lt; ₃ &gt; is hydrogen,
Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group substituted or unsubstituted with Si (CH ₃ ) ₃ , a cyano group or a phenyl group,
L ₁ and L ₂ are single bonds,
L ₃ is a phenylene group,
L ₅ is a single bond, a phenylene group, a naphthylene group or an anthracenylene group,
n is 1 or 2,
o is 0.
11. The method of claim 10,
A compound having the structure of the following formulas d-1 to d-10:
<Formula d-1>

<Formula d-2>

<Formula d-3>

<Formula d-4>

<Formula d-5>

<Formula d-6>

<Formula d-7>

<Formula d-8>

<Formula d-9>

<Formula d-10>

.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups,
Ar ₃ is hydrogen or a phenyl group,
Ar ₄ is a phenyl group, a naphthyl group or an anthracenyl group,
L ₁ , L ₂ and L ₅ are single bonds,
L ₃ is a phenylene group,
m is 1 or 2,
o is 0 or 1.
13. The method of claim 12,
A compound represented by the following formulas (e-1) to (e-11):
&Lt; Formula e-1 >

&Lt; Formula e-2 >

<Formula (e-3)>

<Formula (e-4)>

&Lt; Formula e-5 >

&Lt; Formula e-6 >

&Lt; Formula e-7 >

<Formula e-8>

&Lt; Formula e-9 >

&Lt; Formula e-10 >

&Lt; Formula e-11 >

.
3. The method of claim 2,
Ar ₁ and Ar ₂ are phenyl groups,
Ar ₃ is hydrogen or a phenyl group,
Ar ₄ is a phenyl group or a naphthyl group,
L ₁ and L ₂ are single bonds,
L ₃ is a phenylene group,
L ₅ is a phenylene group, a naphthylene group or an anthracenylene group,
m is 1 or 2,
n is 1,
o is 0 or 1;
15. The method of claim 14,
A compound represented by the following formula (f-1) to (f-14):
<Formula f-1>

<Formula f-2>

<Formula f-3>

<Formula f-4>

<Formula f-5>

<Formula f-6>

<Formula f-7>

<Formula f-8>

<Formula f-9>

<Formula f-10>

<Formula f-11>

<Formula f-12>

<Formula f-13>

<Formula f-14>

.
A first electrode;
An organic layer provided on the first electrode;
A light emitting layer provided on the organic layer;
An electron transporting layer provided on the light emitting layer; And
And a second electrode provided on the electron transporting layer,
Wherein the organic layer comprises a compound represented by the following Formula 1:
[Chemical Formula 1]

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , L ₁ , L ₂ , L ₃ , L ₄ , L ₅ , m and n are as defined in claim ₁ .
17. The method of claim 16,
Wherein the electron transporting layer comprises a compound represented by the following formula (2): &lt; EMI ID =
(2)

In Formula 2,
Z ₁ to Z ₃ independently represent hydrogen, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, An alkoxy group or a diarylphosphine oxide group having 6 to 20 carbon atoms,
When Z ₁ to Z ₃ independently represent an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, or a diarylphosphine oxide group having 6 to 20 carbon atoms, the aryl group, the heteroaryl group And the diarylphosphine oxide group is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a diarylphosphine oxide group having 6 to 20 carbon atoms,
p and q are each independently an integer of 1 to 3;
18. The method of claim 17,
The compound represented by the formula (2) is a compound represented by the following formula (2a)
(2a)

In the above formula (2a)
Ar ₅ is hydrogen, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, an imidazolyl group, a benzothienyl group, a benzoxazolyl group, or a diarylphosphine oxide group,
Z ₂ and Z ₃ independently represent hydrogen, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group,
p and q are independently from each other 1 to 3;
19. The method of claim 18,
Wherein the compound represented by the formula (2a) is selected from the following formulas (2a-1) to (2a-7)
<Formula 2a-1>

&Lt; Formula 2a-2 >

&Lt; Formula 2a-3 >

&Lt; Formula 2a-4 >

<Formula 2a-5>

&Lt; Formula 2a-6 >

<Formula 2a-7>

.
17. The method of claim 16,
The organic layer,
A second organic layer provided between the first electrode and the light emitting layer; And
And a first organic layer provided between the second organic layer and the light emitting layer,
Wherein the first organic layer comprises a compound represented by the general formula (1).
17. The method of claim 16,
The organic layer,
A third organic layer provided between the first electrode and the light emitting layer;
A second organic layer provided between the third organic layer and the light emitting layer; And
And a first organic layer provided between the second organic layer and the light emitting layer,
The first organic layer contains a compound represented by the general formula (1)
Wherein at least one of the second organic layer and the third organic layer comprises a compound represented by the following Formula 3:
(3)

In Formula 3,
R ₄ and R ₆ are each independently an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 30 carbon atoms,
R ₅ is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 4 to 20 carbon atoms,
When R ₅ is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 4 to 20 carbon atoms, the aryl group and the heteroaryl group are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms Substituted or unsubstituted.
22. The method of claim 21,
R ₄ is an alkyl group having 1 to 6 carbon atoms or a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group; Naphthyl group; Or a phenanthryl group,
And R &lt; ₆ &gt; is a methyl group, an ethyl group or a phenyl group.
22. The method of claim 21,
Wherein the compound represented by the formula (3) is a compound represented by the following formula (3a):
[Chemical Formula 3]

.
22. The method according to claim 20 or 21,
Wherein the organic layer further comprises any one or more of any of the remaining organic layers except the first organic layer represented by the following Chemical Formulas 4 to 8:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the general formulas (7) and (8)
R ₇ is a cyano group, a sulfonic group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group,
s and t are independently of each other an integer of 1 to 5;
Y ₁ and Y ₂ are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
The aryl group and the heteroaryl group are each independently substituted with at least one substituent selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a hydroxyl group, and a halogen group Or not.
25. The method of claim 24,
The compound represented by the formula (8) is a compound represented by the following formula (8a) or (8b)
[Chemical Formula 8a]

[Formula 8b]

.
17. The method of claim 16,
The thickness of the organic layer is 5 A to 2,000 A.
22. The method according to claim 20 or 21,
Wherein the first organic layer, the second organic layer, and the third organic layer have a thickness of 5 A to 1,000 A independently of each other.
An electronic device comprising the light emitting element according to claim 16.
29. The method of claim 28,
Wherein the electronic device is a display device or a lighting device.

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