KR101468087B1 - Novel compound, light-emitting device including the compound and electronic device - Google Patents

Abstract

The present invention relates to a novel compound, a light-emitting device and an electronic device including the same. The novel compound is represented by chemical formula 1. <Formula 1> In chemical formula 1, each of Ar_1, Ar_2, Ar_3, Ar_4, L_a, L_b, L_c, L_d and L_e are the same as explained in claim 1.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, a light emitting device and an electronic device including the compound,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound, a light emitting device and an electronic device including the same, and more particularly, to a compound for an organic light emitting device, a light emitting device and an electronic device including the same.

Generally, a light emitting device includes two electrodes facing each other and a light emitting layer containing a light emitting compound interposed between the electrodes. When a current is passed between the electrodes, the light emitting compound generates light. The display device using the light emitting element does not need a separate light source device, so that the weight, size and thickness of the display device can be reduced. Further, the display device using the light emitting element is advantageous in that it has excellent viewing angle, contrast ratio, color reproducibility and the like and low power consumption as compared with a display device using a backlight and a liquid crystal.

The light emitting device may further include a hole transport layer disposed between the anode and the light emitting layer. The hole transport layer can stabilize the interface between the anode and the light emitting layer and minimize the energy barrier therebetween.

However, the light emitting device still has a short emission lifetime 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.

Japanese Patent Application Laid-Open No. 2008-294161 Korea Patent Publication No. 2008-0104025

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a novel compound for improving hole injection and transport ability in a light emitting device.

Another object of the present invention is to provide a light emitting device comprising the above compound.

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

The compound according to one embodiment for realizing the object of the present invention is represented by the following general formula (1).

&Lt; Formula 1 >

In Formula 1,

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, A ring group or a group represented by the following formula (2), Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , At least one of R &lt; 1 &gt; and R &lt; 2 &

(2)

_{L a, L b, L c} , L d and L _e each independently represent a _{* -L 1 -L 2 -L 3 -} * represents,

L ₁ , L ₂ and L ₃ each independently represents a single bond, -O-, -S-, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, a cycloalkyl having 3 to 60 carbon atoms A heterocycloalkylene group having 2 to 60 carbon atoms, or a group represented by the following formula (3)

(3)

Wherein R ₁ , R ₂ , R ₃ and R ₄ each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms ,

At least one of the hydrogens of Formula 1 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxy group And a carboxyl group.

According to another embodiment of the present invention, a light emitting device includes a first electrode, a second electrode, a light emitting layer, and a hole transporting layer containing a compound represented by Formula 1. The first electrode and the second electrode face each other and the light emitting layer may be interposed between the first and second electrodes and the hole transporting layer may be disposed between the first electrode and the light emitting layer .

In one embodiment, the hole transporting layer may comprise a first layer comprising the compound and a P-type dopant, and a second layer comprising the compound. For example, the first layer may be disposed between the first electrode and the light emitting layer, and the second layer may be disposed between the first layer and the light emitting layer. In this case, the second layer may further include a dopant substantially the same as or different from the P-type dopant of the first layer.

According to the novel compound, the light emitting device and the electronic device including the same, the novel compound of the present invention can enhance the hole injection and / or transport ability in the light emitting device.

Further, by using the above compound, the luminous efficiency of the light emitting device can be improved and the lifetime can be increased. In addition, the thermal stability (heat resistance) of the light emitting device can be improved.

1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
3 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.

Hereinafter, a novel compound according to the present invention will be described first, and a light emitting device including the compound will be described in more detail with reference to the accompanying drawings.

The compound according to the present invention is represented by the following formula (1).

&Lt; Formula 1 >

In Formula 1,

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, A ring group or a group represented by the following formula (2), Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , At least one of R &lt; 1 &gt; and R &lt; 2 &

(2)

_{L a, L b, L c} , L d and L _e each independently represent a _{* -L 1 -L 2 -L 3 -} * represents,

L ₁ , L ₂ and L ₃ each independently represents a single bond, -O-, -S-, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, a cycloalkyl having 3 to 60 carbon atoms A heterocycloalkylene group having 2 to 60 carbon atoms, or a group represented by the following formula (3)

(3)

Wherein R ₁ , R ₂ , R ₃ and R ₄ each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms ,

At least one of the hydrogens of Formula 1 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxy group And a carboxyl group.

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

Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, A biphenyl group, a terphenyl group, a chrycenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylene group, A perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, and a phenanthrenyl group.

The "heterocyclic group" refers to an "aromatic heterocycle" or "heterocyclic" derived from a monocyclic or condensed ring. The heterocyclic group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a hetero atom.

Specific examples of the heterocyclic group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group, a triazole group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, An indolyl group, an isoindolyl group, an indolizinyl group, a purinyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, A quinolinyl group, an isoquinolinyl group, a quinolizinyl group, a phthalazinyl group, a naphthylidinyl group, a quinoxalinyl group, a quinazolinyl group, A cinnolinyl group, a pteridinyl group, an imide An imidazotriazinyl group, an acridinyl group, a phenanthridinyl group, a carbazolyl group, a phenanthrolinyl group, a phenazinyl group, a phenanthrolinyl group, An imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, a fused-julolidinyl group represented by the following formula 1-1 or a fused- A nitrogen-containing heteroaryl group including a julolidinyl group represented by the following formula (1-2); 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 heterocyclic group include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, a phenothiazyl group, an isoxazolyl group, a phenoxazinyl group, an oxazolyl group, a benzoxazolyl group, an oxadiazole group, an oxazolyl group, an oxazolyl group, Include compounds containing at least two heteroatoms such as an oxadiazolyl group, pyrazoloxazolyl group, imidazothiazolyl group, thienofuranyl group and the like. have.

[Formula 1-1] [Formula 1-2]

In Formula 1-1, Q ₁ and Q ₂ each independently represent an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms,

Each of R _a , R _b , R _c , R _d , R _e and R _f is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, &Lt; / RTI &gt; or a heteroaryl group having from 2 to 20 carbon atoms.

In Formula 1-2, R _g , R _h , R _i and R _j are each independently selected from the group consisting of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, And a heteroaryl group having 2 to 20 carbon atoms.

Here, the heteroaryl group in each of formulas (1-1) and (1-2) is substantially the same as the above-mentioned heterocyclic group. However, the heteroaryl group may not include the fused-cellulose dienyl group represented by the formula (1-1) and the cellulose dienyl group represented by the formula (1-2). Hereinafter, the "heteroaryl group" is substantially the same as that described in formulas (1-1) and (1-2).

"Alkyl group" is defined as a functional group derived from a linear or branched saturated hydrocarbon.

Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, Dimethylpropyl group, 2-dimethylpropyl group, 1-ethylpropyl group, 2-ethylpropyl group (2, ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl- 2-methylpropyl group, 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group, A 2-methylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 2,2-dimethylbutyl group, 2,2-dimeth 1-butylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2- Methylpentyl group, 3-methylpentyl group, and the like.

The "arylene group" may mean a divalent substituent derived from the above-described aryl group.

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

In one embodiment, the compound represented by Formula 1 may include a compound represented by Formula 4 below.

&Lt; Formula 4 >

In Formula 4,

Ar ₂ , Ar ₃ and Ar ₄ each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, (5), &lt; / RTI &gt;

&Lt; Formula 5 >

_{L a, L b, L c} , L d and L _e each independently represent a _{* -L 1 -L 2 -L 3 -} * represents,

L ₁ , L ₂ and L ₃ each independently represents a single bond, -O-, -S-, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, A heterocycloalkylene group having 2 to 30 carbon atoms, or a group represented by the following formula (6)

(6)

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms,

At least one of the hydrogens of Formula 4 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxy group And a carboxyl group.

For example, the heterocyclic group of the formula (1) may be represented by the following formula (7-1) or (7-2).

&Lt; Formula 7-1 > < Formula 7-2 &

In each of formulas (7-1) and (7-2), R ₇ , R ₈ , R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 6 carbon atoms.

In one embodiment, the compound represented by Formula 4 may include a compound represented by Formula 8 below.

(8)

In Formula 8, Ar ₂ may represent any one selected from the following Table 1.

Type of substituent One

5

2

6

3

7

4

8

In Formula 8, Ar ₃ and Ar ₄ may each independently represent hydrogen or any one selected from the following Table 2.

Type of substituent One

4

2

5

3

6

In the formula (8), L _a may represent a single bond or any one selected from the following Table 3.

Type of substituent One

4

2

5

3

6

In Formula 8, R ₁ and R ₂ each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group.

For example, in the case of the substituent at the 5-position in Table 1, specifically, it may be represented by the following formula 1-1a or 1-1b.

&Lt; Formula 1-1a > < Formula 1-1b &

Substituent 6 of Table 1 can be represented by the following Formula 1-2a or Formula 1-2b.

&Lt; Formula 1-2a > < Formula 1-2b &

The substituent at the 5th position in Table 2 may be represented by the following formula (2-1a) or (2-1b).

(2-1a) < Formula (2-1b) >

Substituent 6 of Table 2 can be represented by the following formula (2-2a) or (2-2b).

(2-2a) < Formula (2-2b) >

Each of the substituents in Tables 1 to 3 may have various bonding positions in the indicated range, and redundant descriptions will be omitted.

In one embodiment, the compound represented by the formula (1) may be any one selected from the compounds represented by the following Structures 1 to 36.

<Structure 1> <Structure 2>

<Structure 3><Structure4>

<Structure 5> <Structure 6>

<Structure 7><Structure8>

<Structure 9>

<Structure 10>

<Structure 11>

<Structure 12>

<Structure 13>

<Structure 14>

<Structure 15>

<Structure 16>

<Structure 17> <Structure 18>

<Structure 19>

<Structure 20>

<Structure 21> <Structure 22>

<Structure 23> <Structure 24>

<Structure 25> <Structure 26>

<Structure 27> <Structure 28>

<Structure 29>

<Structure 30>

<Structure 31>

<Structure 32>

<Structure 33>

<Structure 34>

<Structure 35>

<Structure 36>

Hereinafter, a light emitting device including a novel compound according to the present invention will be described with reference to the accompanying drawings. The structure of the light emitting device including the compound is not limited by the accompanying drawings and the following description.

1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.

Referring to FIG. 1, a light emitting device 100 includes a first electrode 20, a hole transporting layer 30, a light emitting layer 40, and a second electrode 50 formed on a base substrate 10. The light emitting device 100 may be an organic light emitting diode (OLED).

The first electrode 20 may be formed on the base substrate 10 with a conductive material. For example, the first electrode 20 may be a transparent electrode. At this time, the first electrode 20 may be formed of indium tin oxide (ITO). Alternatively, the first electrode 20 may be an opaque (reflective) electrode. At this time, the first electrode 20 may have an ITO / silver (Ag) / ITO structure. The first electrode 20 may be an anode of the light emitting device 100.

The hole transporting layer 30 is formed on the first electrode 20 and is interposed between the first electrode 20 and the light emitting layer 40. The hole transporting layer (30) includes a compound represented by the following formula (1) as a hole transporting compound.

[Chemical Formula 1]

The compound represented by the above formula (1) is substantially the same as that described above as a novel compound according to the present invention. Therefore, a detailed description of _{Ar 1, Ar 2, Ar 3} , Ar 4, L a, L b, L c, L d and L _e is omitted.

The wavelength of the light emitted by the light emitting layer 40 may vary depending on the type of the compound forming the light emitting layer 40.

The second electrode 50 may be formed on the light emitting layer 40 as a conductive material. When the first electrode 20 is a transparent electrode, the second electrode 50 may be an opaque (reflective) electrode. At this time, the second electrode 50 may be an aluminum electrode. Alternatively, when the first electrode 20 is an opaque electrode, the second electrode 50 may be a transparent or semi-transparent electrode. At this time, the second electrode 50 may have a thickness of 100 ANGSTROM to 150 ANGSTROM and may be an alloy including magnesium and silver. The second electrode 50 may be a cathode of the light emitting device 100.

An electron transport layer and / or an electron injection layer may be formed as an electron transporting layer between the light emitting layer (40) and the second electrode (50).

A hole injected from the first electrode 20 to the light emitting layer 40 and a hole injected from the first electrode 20 to the light emitting layer 40, Electrons injected from the second electrode 50 into the light emitting layer 40 are coupled to form an exciton. During the transition of the excitons to the ground state, light having a wavelength of a specific region is generated. At this time, the exciton may be a singlet exciton, and may also be a triplet exciton. Accordingly, the light emitting device 100 can provide light to the outside.

Although not shown, the light emitting device 100 includes an electron transporting layer (ETL) and an electron injecting layer (EIL) disposed between the light emitting layer 40 and the second electrode 50, As shown in FIG. The electron transport layer and the electron injection layer may be sequentially stacked on the light emitting layer 40.

The light emitting device 100 may include a first blocking layer (not shown) disposed between the first electrode 20 and the light emitting layer 40 and / And a second barrier layer (not shown) disposed between the first barrier layer and the second barrier layer.

For example, the first blocking layer is disposed between the hole transporting layer 30 and the light emitting layer 40, so that electrons injected from the second electrode 50 pass through the light emitting layer 40, And an electron blocking layer (EBL) for preventing the electrons from entering the transporting layer 30. The first blocking layer may be an exciton blocking layer which prevents the excitons formed in the light emitting layer 40 from diffusing toward the first electrode 20 to prevent the excitons from disappearing due to non-emission. In addition, the first blocking layer may be an exciton dissociation blocking layer (EDBL). The exciton isolation barrier layer prevents excitons formed in the light emitting layer 40 from undergoing 'exciton dissociation' at the interface between the light emitting layer 40 and the hole transporting layer 30, can do. In order to prevent exciton separation at the interface, the compound forming the first blocking layer may be selected to have a HOMO value at a level similar to that of the compound forming the light-emitting layer 40.

At this time, the first barrier layer may include the compound according to the present invention described above.

The second blocking layer is disposed between the light emitting layer 40 and the second electrode 50, specifically between the light emitting layer 40 and the electron transporting layer, and holes are injected from the first electrode 20 to the light emitting layer 40 Hole blocking layer (HBL) for preventing the electrons from being introduced into the electron transporting layer via the hole blocking layer (HBL). The second blocking layer may be an exciton blocking layer which prevents the excitons formed in the light emitting layer 40 from diffusing toward the second electrode 50 to prevent the excitons from disappearing due to non-emission.

If the thickness of each of the first and second barrier layers is adjusted to the resonance length of the light emitting device 100, the efficiency of light emission can be increased, and excitons can be formed at the center of the light emitting layer 40 .

2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.

Referring to FIG. 2, the light emitting device 102 includes a first electrode 20, a hole transporting layer 32, a light emitting layer 40, and a second electrode 50 formed on a base substrate 10. The hole transporting layer 32 is substantially the same as that described with reference to FIG. 1, so that duplicated description is omitted.

The hole transporting layer (32) includes a compound represented by the above formula (1) and a P-type dopant. The compounds contained in the hole-transporting layer 32 are substantially the same as those described above, and therefore duplicate detailed descriptions are omitted.

The P-type dopant may include a P-type organic dopant and / or a P-type inorganic material dopant.

Specific examples of the P-type organic dopant include compounds represented by the following Chemical Formulas 9 to 13, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanoantho-2,6-quinodimethane (3, 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane (3, &lt; RTI ID = 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ) or tetracyanoquinodimethane (TCNQ). These may be used alone or in combination of two or more.

[Chemical Formula 9]

In the above formula (9), R represents a cyano group, a sulfonic group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group.

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In Formula 13, m and n each independently represent an integer of 1 to 5, and Y ₁ and Y ₂ each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms. In the formula (13), hydrogen of the aryl group or heteroaryl group represented by Y ₁ and Y ₂ may be substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a hydroxy group, Or the unsubstituted hydrogens of Y ₁ and Y ₂ may each independently be substituted or unsubstituted with a halogen group.

For example, the compound represented by Formula 13 may include a compound represented by Formula 13a or 13b.

[Chemical Formula 13a]

[Chemical Formula 13b]

Examples of the P-type inorganic material dopant include metal oxides and metal halides. Specific examples of the P-type inorganic material dopant include MoO ₃ , V ₂ O ₅ , WO ₃ , SnO ₂ , ZnO, MnO ₂ , CoO ₂ , ReO ₃ , TiO _{2 ,} FeCl ₃ , SbCl ₅ or MgF ₂ . These may be used alone or in combination of two or more.

The P-type dopant may be about 0.5 parts by weight to about 20 parts by weight based on 100 parts by weight of the novel compound according to the present invention which is a hole-transporting compound. For example, the P-type dopant may be about 0.5 to about 15 parts by weight, or about 0.5 to about 5 parts by weight based on 100 parts by weight of the hole transporting compound. Alternatively, the P-type dopant may be used in an amount of about 1 to 10 parts by weight, 1 to 5 parts by weight, 1.5 to 6 parts by weight, or 2 to 5 parts by weight per 100 parts by weight of the hole- .

When the content of the P-type dopant is about 0.5 parts by weight to about 20 parts by weight per 100 parts by weight of the hole transporting compound, the P-type dopant does not cause excessive leakage currents without deteriorating the physical properties of the hole- . Further, the P-type dopant can reduce the energy barrier at the interface with each of the upper and lower layers in contact with the hole transporting layer 32.

Although not shown in the drawing, the light emitting device 102 may further include an electron transport layer, an electron injection layer, a first blocking layer, and / or a second blocking layer. Each of the layers is substantially the same as that described in the light emitting device 100 of FIG. 1, and thus a detailed description thereof will be omitted. When the light emitting device 102 includes the first blocking layer, the first blocking layer may include the compound according to the present invention described above.

Meanwhile, the light emitting device 100 shown in FIG. 1 may further include an interlayer (not shown). The intermediate layer may be disposed between the first electrode 20 of FIG. 1 and the hole transporting layer 30, and may be formed of a compound used as the P-type dopant described in FIG.

3 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.

Referring to FIG. 3, the light emitting device 104 includes a first electrode 20, a hole transporting layer 34, a light emitting layer 40, and a second electrode 50 formed on a base substrate 10. The hole transporting layer 34 is substantially the same as that described with reference to FIG. 1, so that duplicated description is omitted.

The hole transporting layer 34 includes a first layer 33a in contact with the first electrode 20 and a second layer 33b disposed between the first layer 33a and the light emitting layer 40 do. That is, the hole transporting layer 34 may have a two-layer structure. Further, the hole transporting layer 34 may have a multilayer structure of two or more layers including the first and second layers 33a and 33b.

The first and second layers 33a and 33b may include the same kind of hole transporting compound. By making the components of the hole transporting compound contained in the first layer 33a and the second layer 33b the same, physico-chemical defects that may occur at the interface between the dissimilar materials are reduced to facilitate hole injection into the light emitting layer . In another aspect, using the same host material for the first layer 33a and the second layer 33b allows for the continuous formation of the first layer 33a and the second layer 33b in one chamber The manufacturing process is simplified and the manufacturing time can be shortened. Furthermore, since the physical properties such as the glass transition temperature between the adjacent layers become similar, there is an advantage that the durability of the device can be enhanced.

The first layer 33a includes a novel compound according to the present invention represented by Formula 1 and a P-type dopant as a hole-transporting compound. The first layer 33a is substantially the same as the hole transporting layer 32 described in Fig. 2 except for the thickness. Therefore, redundant description is omitted.

The second layer 33b includes a novel compound according to the present invention represented by Formula 1 as the hole-transporting compound, and the hole-transporting compound constituting the second layer 33b includes the first layer 33a May be the same as the hole-transporting compound to be constituted. The second layer 33b is substantially the same as the hole transporting layer 30 described above with reference to FIG. 1 except for the thickness, so that detailed description is omitted.

Alternatively, the first and second layers 33a and 33b may include different kinds of hole transporting compounds. The first and second layers (33a, 33b) of the hole-transporting compound, which configuration is being novel compounds according to the invention represented by the formula _{1, Ar 1, Ar 2,} Ar 3, Ar 4, L a, L _b , L _c , L _d and L _e may each independently be different. At this time, the compound constituting each of the first and second layers 33a and 33b may be selected to have a HOMO value for efficiently transferring holes to the light emitting layer 40.

In addition, the second layer 33b may further include a P-type dopant together with the hole transporting compound. At this time, the P-type dopants to be doped in the first layer 33a and the second layer 33b may be different from each other, and the doping amount may be varied even if the same kind is used. For example, the content (P1) of the P-type dopant doped in the first layer (33a) and the content (P2) of the P-type dopant doped in the second layer (33b) satisfy the following relationship Can be satisfied.

[Equation 1]

P1 / P2? 1

In the above formula (1), "P1" is the content of the P-type dopant doped with respect to 100 parts by weight of the hole transporting compound in the first layer 33a and "P2" is the content of the hole transporting compound 100 Is the content of doped P-type dopant relative to parts by weight.

For example, the content of the P-type dopant doped in the first layer 33a may be 0.3 to 20 parts by weight, 1 to 15 parts by weight, 2 to 10 parts by weight, or 4 to 10 parts by weight based on 100 parts by weight of the hole- To 6 parts by weight. The content of the P-type dopant doped in the second layer 33b is 0.3 to 20 parts by weight, 0.5 to 10 parts by weight, 1 to 8 parts by weight, or 2 to 4 parts by weight, based on 100 parts by weight of the hole- Can be negative.

Further, although not shown in the drawing, the light emitting device 104 may further include an electron transport layer, an electron injection layer, a first blocking layer, and / or a second blocking layer. Each of the layers is substantially the same as that described in the light emitting device 100 of FIG. 1, and thus a detailed description thereof will be omitted.

Each of the light emitting devices 100, 102, and 104 described above includes the novel compound according to the present invention represented by Formula 1, thereby improving the light emitting efficiency of the light emitting devices 100, 102 and 104, Can be prolonged.

Although the light emitting devices 100, 102 and 104 are directly formed on the base substrate 10 in FIGS. 1 to 3, the light emitting devices 100, A thin film transistor may be disposed between the one electrode 20 and the base substrate 10 as a driving element for driving a pixel. At this time, the first electrode 20 may be a pixel electrode connected to the thin film transistor. When the first electrode 20 is a pixel electrode, the first electrodes 20 are arranged separately from each other in a plurality of pixels, and the first electrode 20 is disposed on the base substrate 10 along the edge of the first electrode 20 The barrier rib patterns may be formed and the layers stacked on the first electrodes 20 disposed adjacent to each other may be isolated from each other. That is, although not shown in the drawings, the light emitting devices 100, 102, and 104 may be used in a display device that displays an image without a backlight.

Further, the light emitting devices 100, 102, and 104 may be used as a lighting device.

As described above, the light emitting devices 100, 102, and 104 exemplified in the present invention can be used in various electronic devices such as the display device or the lighting device.

Hereinafter, the novel compounds according to the present invention will be described in more detail with reference to specific examples of the present invention. The embodiments illustrated below are for the purpose of illustrating the present invention only and are not intended to limit the scope of the present invention.

Example  One

Compound A (20.55 mmol, 10 g), Compound B (22.60 mmol, 6.53 g) and palladium acetate (Pd (OAc) ₂ ) (0.411 mmol, 0.09 g) were charged in a 250 mL three- , sodium tert - butoxide (sodium tert -butoxide) (24.66 mmol , 2.37 g), o - xylene (o -xylene) 50 mL and tri - tert - butylphosphine (50w / w% tri- tert -butylphosphine in xylene) (2.055 mmol, 0.4 mL) was added thereto, followed by heating at 130 占 폚 for 3 hours.

The reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 300 mL of methanol, and stirred for 20 minutes. This was filtered to give about 12 g (84% yield) of compound 1 as a light gray solid.

MALDI-TOF: m / z = 694.2765 (C 50 H 38 N 2 Si = 694.3)

Example  2

A 250 mL three-necked round bottom flask was charged with nitrogen and then Compound A (30.82 mmol, 15 g), Compound C (33.90 mmol, 14 g), palladium acetate (0.616 mmol, 0.13 g), sodium tert -butoxide 36.99 mmol, 3.55 g), o - xylene, 75 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (3.082 mmol, 0.4 mL), 5 hours at 135 ℃ Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 400 mL of methanol, and stirred for 25 minutes. This was filtered to give about 20 g (yield 80%) of compound 2 as a gray solid.

MALDI-TOF: m / z = 819.2518 (C ₆₀ H ₄₂ N ₂ Si = 818.3)

Example  3

A 250 mL three-necked round bottom flask was charged with nitrogen and then compound D (19.39 mmol, 12 g), compound B (31.33 mmol, 6.16 g), palladium acetate (0.387 mmol, 0.08 g), sodium tert- 23.27 mmol, 2.23 g), o - xylene, 60 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (1.939 mmol, 0.5 mL), in 130 ℃ 4 sigan Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 60 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 350 mL of methanol, and stirred for 30 minutes. Filtration gave about 13 g (81% yield) of compound 3 as a light gray solid.

MALDI-TOF: m / z = 826.2011 (C ₅₈ H ₄₆ N ₂ Si ₂ = 826.3)

Example  4

A 250 mL three-necked round bottom flask was charged with nitrogen and then charged with compound E (16.16 mmol, 10 g), compound B (17.77 mmol, 5.14 g), palladium acetate (0.323 mmol, 0.07 g), sodium tert- 19.39 mmol, 1.86 g), o - xylene, 50 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (1.616 mmol, 0.4 mL), 5 hours at 130 ℃ Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 300 mL of methanol, and stirred for 20 minutes. This was filtered to give about 11 g (82% yield) of Compound 4 as a gray solid.

MALDI-TOF: m / z = 826.2089 (C ₅₈ H ₄₆ N ₂ Si ₂ = 826.3)

Example  5

A 250 mL three-necked round bottom flask was charged with nitrogen and then charged with compound F (25.30 mmol, 15 g), compound B (27.83 mmol, 8.0 g), palladium acetate (0.506 mmol, 0.11 g), sodium tert- 30.36 mmol, 2.91 g), o - xylene, 75 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (2.530 mmol, 0.6 mL), 7 hours at 130 ℃ Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 500 mL of methanol, and stirred for 40 minutes. This was filtered to give about 18 g (yield 88%) of compound 5 as a light brown solid.

MALDI-TOF: m / z = 800.2890 (C ₅₆ H ₄₀ N ₂ SSi = 800.3)

Example  6

A 500 mL three-neck round bottom flask was charged with nitrogen and then charged with compound G (37.70 mmol, 20 g), compound H (41.47 mmol, 7.0 g), palladium acetate (0.754 mmol, 0.17 g), sodium tert- 45.24 mmol, 4.34 g), o - xylene 100 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (3.770 mmol, 0.9 mL), 2 hours at 130 ℃ Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 100 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 500 mL of methanol, and stirred for 60 minutes. This was filtered to give about 20 g (86% yield) of Compound 6 as an ivory solid.

MALDI-TOF: m / z = 618.3269 (C ₄₄ H ₃₄ N ₂ Si = 618.3)

Example  7

A 250 mL three-neck round bottom flask was charged with nitrogen and then Compound I (17.34 mmol, 10 g), Compound B (19.07 mmol, 5.51 g), palladium acetate (0.346 mmol, 0.07 g), sodium tert- 20.80 mmol, 2.0 g), o - xylene, 50 mL and tri - tert - insert the butylphosphine (50w / w% tri- tert -butylphosphine in xylene) (1.734 mmol, 0.4 mL), in 130 ℃ 3 sigan Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 300 mL of methanol, and stirred for 50 minutes. This was filtered to give about 12 g (yield 88%) of compound 7 as a light-colored solid.

MALDI-TOF: m / z = 784.2910 (C ₅₆ H ₄₀ N ₂ OSi = 784.3)

Example  8

A 250 mL three-neck round bottom flask was charged with nitrogen and then compound J (20.63 mmol, 15 g), compound C (22.69 mmol, 6.56 g), palladium acetate (0.412 mmol, 0.09 g), sodium tert- 24.76 mmol, 2.38 g), o - xylene, 75 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (2.063 mmol, 0.5 mL), 5 hours at 135 ℃ Lt; / RTI &gt;

The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 500 mL of methanol, and stirred for 50 minutes. Filtration gave about 17 g (yield: 88%) of compound 8 as a light brown solid.

MALDI-TOF: m / z = 934.3744 (C ₆₉ H ₅₀ N ₂ Si = 934.4)

Comparative Example  1 to 3

Compounds having the following structures a, b and c were commercially available or prepared and used in Comparative Examples 1 to 3, respectively.

(A)

[Formula b]

(C)

Production of Light-Emitting Devices A-1 to A-8

A compound according to Example 1 was deposited as a host material of the hole transporting layer 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 about 3 parts by weight with respect to 100 parts by weight of the host material to form a 100 Å-thick first layer. The compound of Example 1 was deposited on the first layer to a thickness of 300 Å to form a second layer.

The second layer to the Ir (ppy) ₃ represented by mCBP and formula (16) represented by the general formula (15) 100 over: the mCBP again on the co-deposition to 9 weight ratio to form a light emitting layer of about 400Å thickness, and the light-emitting layer to approximately 50Å thickness Followed by deposition to form a blocking layer.

Next, a compound represented by the following formula (17) and Liq represented by the following formula (18) were co-deposited on the barrier layer at a weight ratio of 50:50 to form an electron transport layer having a thickness of about 360 Å. Next, an electron injecting layer having a thickness of about 5 Å was formed on the electron transporting layer using Liq represented by the following formula (18).

On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 ANGSTROM was formed.

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

A light-emitting element A-1 comprising the compound according to Example 1 of the present invention was prepared by the above method.

Further, the light-emitting element A-1 was produced except that each of the compounds according to Examples 2 to 8 was used instead of the compound according to Example 1 as the host material of the first layer and the second layer The light-emitting elements A-2 to A-8 were produced through substantially the same steps as those of the light-emitting elements A-1 to A-8.

Preparation of Comparative Devices 1 to 3

Substantially the same as the process for producing the light-emitting element A-1 except that the compound according to Comparative Examples 1 to 3 was used instead of the compound according to Example 1 as the host material of the first layer and the second layer Comparative elements 1 to 3 were prepared through the process.

Power efficiency and lifetime evaluation of light emitting device -1

A UV curing sealant was dispensed onto the edge of the cover glass to which the moisture absorber (Getter) was attached in the glove box of the nitrogen atmosphere for each of the light emitting elements A-1 to A-8 and the comparative elements 1 to 3, And each of the comparative elements and the cover glass were cemented together and cured by irradiation with UV light. Power efficiency was measured with respect to the light emitting devices A-1 to A-8 and Comparative Devices 1 to 3 prepared as described above with reference to a value at a luminance of 1,000 cd / m ² . The results are shown in Table 4. The lifetime of each of the light-emitting elements A-1 to A-8 and the comparative elements 1 to 3 was measured using Polarronix M6000S (trade name, Mac Science Ltd., Korea) as a life time measuring instrument. The results are shown in Table 4.

In Table 4, the unit of the result of measuring the power efficiency is lm / W. In Table 4, T ₈₀ denotes a time taken for the luminance of the light emitting device to reach 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m ² . Values for lifetime can be converted on the basis of a conversion equation known to those skilled in the art.

Device No. Power Efficiency [lm / W] Life span (T ₈₀ [hr]) Light-emitting element A-1 27.8 151 Light-emitting element A-2 29.9 169 Light emitting element A-3 24.8 141 Light-emitting element A-4 25.9 159 Light-emitting element A-5 19.8 127 Light-emitting element A-6 22.5 135 Light emitting element A-7 17.4 113 Light-emitting element A-8 20.7 119 Comparison device 1 11.3 66 Comparison device 2 14.8 79 Comparison device 3 12.9 71

Referring to Table 4, the power efficiencies of the light emitting elements A-1 to A-8 are 27.8 lm / W, 29.9 lm / W, 24.8 lm / W, 25.9 lm / W, 19.8 lm / W, 22.5 lm / 17.4 lm / W and 20.7 lm / W, respectively. That is, the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is at least about 17.4 lm / W. On the other hand, since the power efficiencies of the comparative devices 1 to 3 are 11.3 lm / W, 14.8 lm / W and 12.9 lm / W, power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention Which is better than the power efficiency of the comparative elements 1 to 3. Particularly, when comparing the comparative element 2 having the maximum power efficiency among the comparative elements 1 to 3 and the light-emitting element A-7 having the minimum power efficiency among the light-emitting elements A-1 to A-8, It can be seen that the power efficiency of the device is increased by at least about 17%.

The life span of each of the light emitting elements A-1 to A-8 is 151 hours, 169 hours, 141 hours, 159 hours, 127 hours, 135 hours, 113 hours and 119 hours, 66 hours, 79 hours and 71 hours. When comparing the lifetime of the comparative element 2 with the lifetime of the light-emitting element A-7, the lifetime of the light-emitting element using the compound according to the present invention is at least about 43% longer.

Production of Light-Emitting Devices B-1 to B-8

A first layer is formed by depositing HAT-CN represented by Chemical Formula 14 to a thickness of about 100 Å on a first electrode formed of indium tin oxide (ITO), and NPB (N, N ' -diphenyl-N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'-diamine was deposited to a thickness of about 300 Å to form a second layer.

A first blocking layer having a thickness of about 100 Å was formed on the second layer on the basis of the compound of Example 1, and mCBP represented by Formula 15 and Ir (ppy) ₃ represented by Formula 16 were formed on the first blocking layer. Was co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 400 Å. MCBP was again deposited on the light emitting layer to a thickness of about 50 Å to form a second blocking layer.

Next, the compound represented by Formula 17 and Liq represented by Formula 18 were co-deposited on the second blocking layer at a weight ratio of 50:50 to form an electron transport layer having a thickness of about 360 Å. Next, Liq was deposited again on the electron transport layer to a thickness of about 5 Å to form an electron injection layer.

A second electrode using an aluminum thin film having a thickness of 1,000 A was formed on the electron injection layer to prepare a light emitting device B-1 including the compound according to Example 1 of the present invention.

The above-described first barrier layer was produced by using each of the compounds according to Examples 2 to 8 of the present invention instead of the compound according to Example 1 of the present invention, Light-emitting elements B-2 to B-8 were produced through substantially the same processes as those of the above.

Preparation of Comparative Devices 4 to 6

Comparative Device 4 was manufactured in substantially the same process except that the first barrier layer was prepared using the compound according to Comparative Example 1 represented by Formula a in the process of producing the light-emitting device B-1.

Further, in the step of producing the light-emitting element B-1, the first barrier layer was prepared by using substantially the same process except that the compound according to Comparative Examples 2 and 3 represented by Formula b and Formula c was used. Devices 5 and 6 were respectively fabricated.

Power efficiency and lifetime evaluation of light emitting device-2

The luminance efficiency of the light emitting devices B-1 to B-8 and the comparison devices 4 to 6 prepared in the above-described manner was substantially the same as that of the light emitting devices A-1 to A- m &lt; ² &gt;.

In addition, the lifetime of each of the light-emitting elements B-1 to B-8 and the comparative elements 4 to 6 was measured in substantially the same manner as the lifetime evaluation experiment for the light-emitting elements A-1 to A-8.

Table 5 shows the results of power efficiency and lifetime of each of the light-emitting elements B-1 to B-8 and the comparative elements 4 to 6. In Table 5, the unit of the result of measuring the power efficiency is lm / W. In Table 5, T ₈₀ represents the time taken for the luminance of the light emitting device to reach 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m ² . Values for lifetime can be converted on the basis of a conversion equation known to those skilled in the art.

Device No. Power Efficiency [lm / W] Life span (T ₈₀ [hr]) Light-emitting element B-1 25.9 114 Light Emitting Device B-2 27.4 137 Light Emitting Device B-3 28.6 129 Light Emitting Device B-4 26.3 116 Light Emitting Device B-5 35.7 148 Light Emitting Device B-6 33.8 159 Light Emitting Device B-7 34.5 163 Light Emitting Device B-8 29.2 141 Comparison device 4 12.7 73 Comparison device 5 15.9 83 Comparison device 6 14.2 76

The power efficiencies of the light emitting devices B-1 to B-8 are 25.9 lm / W, 27.4 lm / W, 28.6 lm / W, 26.3 lm / W, 35.7 lm / W, 33.8 lm / 34.5 lm / W and 29.2 lm / W, respectively. On the other hand, the power efficiencies of the comparative devices 4 to 6 are 12.7 lm / W, 15.9 lm / W and 14.2 lm / W, respectively. That is, it can be seen that the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is better than that of Comparative Devices 4 to 6. Particularly, when comparing the comparative element 5 having the maximum power efficiency among the comparative elements 4 to 6 and the light-emitting element B-1 having the minimum power efficiency among the light-emitting elements B-1 to B-8, The power efficiency of the device is increased by at least about 62%.

The lifetimes of the light-emitting elements B-1 to B-8 were 114 hours, 137 hours, 129 hours, 116 hours, 148 hours, 159 hours, 163 hours, and 141 hours, respectively, Hour, 83 hours, and 76 hours, respectively. It can be seen that the lifetime of the light emitting device using the compound according to the present invention is at least 37% longer when the life span of the comparison device 5 and the lifetime of the light emitting device B-1 are compared.

Production of Light-Emitting Devices C-1 to C-8

NPB was deposited as a host material of the hole transporting layer at a rate of 1 Å / sec on the first electrode formed of indium tin oxide (ITO), and at the same time, a P type dopant (HAT-CN) And about 3 parts by weight with respect to 100 parts by weight of the first layer were co-deposited to form a 100 Å-thick first layer. NPB was deposited on the first layer to a thickness of 300 ANGSTROM to form a second layer. A first blocking layer having a thickness of about 100 Å was formed on the second layer on the basis of the compound of Example 1, and mCBP represented by Formula 15 and Ir (ppy) ₃ represented by Formula 16 were formed on the first blocking layer. Was co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 400 Å. MCBP was again deposited on the light emitting layer to a thickness of about 50 Å to form a second blocking layer.

Next, the compound represented by Formula 17 and Liq represented by Formula 18 were co-deposited on the second blocking layer at a weight ratio of 50:50 to form an electron transport layer having a thickness of about 360 Å. Next, an electron injection layer having a thickness of about 5 Å was formed on the electron transport layer using Liq.

A second electrode using an aluminum thin film having a thickness of 1,000 A was formed on the electron injection layer to prepare a light emitting device C-1 including the compound according to Example 1 of the present invention.

1 except that the first blocking layer was prepared using each of the compounds according to Examples 2 to 8 of the present invention instead of the compound according to Example 1, Light-emitting elements C-2 through C-8 were produced through substantially the same process.

Preparation of Comparative Devices 7 to 9

Comparative Device 7 was prepared in substantially the same process except that the first barrier layer was prepared using the compound according to Comparative Example 1 represented by Formula a in the process of producing the light-emitting device C-1.

Further, in the process for producing the above-described light-emitting element C-1, the first barrier layer was prepared by using substantially the same process except that the compound according to Comparative Example 2 and 3 represented by Formula b and Formula c was used Devices 8 and 9 were respectively fabricated.

Power Efficiency and Lifetime Evaluation of Light Emitting Device-3

The light emitting devices C-1 to C-8 and the comparative devices 7 to 9 prepared in the above-described manner were tested for luminance efficiency of 1,000 cd / m &lt; 2 &gt; m &lt; ² &gt;.

The lifetime of each of the light-emitting elements C-1 to C-8 and the comparative elements 7 to 9 was measured in the same manner as the life evaluation test for the light-emitting elements A-1 to A-10.

Table 6 shows the results of power efficiency and lifetime of each of the light-emitting elements C-1 to C-8 and the comparative elements 7 to 9. In Table 6, the unit of the result of measuring the power efficiency is lm / W. In Table 6, T ₈₀ denotes a time taken for the luminance of the light emitting device to reach 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m ² . Values for lifetime can be converted on the basis of a conversion equation known to those skilled in the art.

Device No. Power Efficiency [lm / W] Life span (T ₈₀ [hr]) Light-emitting element C-1 26.8 119 Light Emitting Device C-2 28.9 141 Light-emitting element C-3 29.1 137 Light emitting element C-4 27.8 122 Light emitting element C-5 36.8 157 Light Emitting Device C-6 34.7 165 Light Emitting Device C-7 35.9 179 Light Emitting Device C-8 30.7 150 Comparison device 7 13.8 83 Comparison device 8 16.3 91 Comparison device 9 15.1 85

The power efficiency of each of the light emitting devices C-1 to C-8 is 26.8 lm / 35.9 lm / W and 30.7 lm / W, respectively. On the other hand, the power efficiencies of the comparative devices 7 to 9 are 13.8 lm / W, 16.3 lm / W and 15.1 lm / W, respectively. That is, it can be seen that the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is better than that of Comparative Devices 7 to 9. Particularly, when comparing the comparative element 8 having the maximum power efficiency among the comparative elements 7 to 9 and the light-emitting element C-1 having the minimum power efficiency among the light-emitting elements C-1 to C-8, It can be seen that the power efficiency of the device has been increased by at least about 64%.

The life span of the light emitting elements C-1 to C-8 is 119 hours, 141 hours, 137 hours, 122 hours, 157 hours, 165 hours, 179 hours and 150 hours respectively, Hour, 91 hours and 85 hours. When comparing the lifetime of the comparison device 8 with that of the light-emitting device C-1, the lifetime of the light-emitting device using the compound according to the present invention is at least 30% longer.

100, 102, 104: light emitting element 10: base substrate
20: first electrode 30, 32, 34: hole transport layer
33a: first layer 33b: second layer
40: light emitting layer 50: second electrode

Claims (10)

A compound represented by the following formula (1);
&Lt; Formula 1 >

In Formula 1,
Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, A ring group or a group represented by the following formula (2), Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , At least one of R < 1 > and R < 2 &
(2)

_{L a, L b, L c} , L d and L _e each independently represent a _{* -L 1 -L 2 -L 3 -} * represents,
L ₁ , L ₂ and L ₃ each independently represents a single bond, -O-, -S-, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, a cycloalkyl having 3 to 60 carbon atoms A heterocycloalkylene group having 2 to 60 carbon atoms, or a group represented by the following formula (3)
(3)

Wherein R ₁ , R ₂ , R ₃ and R ₄ each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms ,
At least one of the hydrogens of Formula 1 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxy group And a carboxyl group.
The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 4 below.
&Lt; Formula 4 >

In Formula 4,
Ar ₂ , Ar ₃ and Ar ₄ each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, (5), < / RTI >
&Lt; Formula 5 >

_{L a, L b, L c} , L d and L _e each independently represent a _{* -L 1 -L 2 -L 3 -} * represents,
L ₁ , L ₂ and L ₃ each independently represents a single bond, -O-, -S-, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, A heterocycloalkylene group having 2 to 30 carbon atoms, or a group represented by the following formula (6)
(6)

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms,
At least one of the hydrogens of Formula 4 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxy group And a carboxyl group.
The compound according to claim 1, wherein the heterocyclic group is
A compound represented by the following formula (7-1) or (7-2):
&Lt; Formula 7-1 >< Formula 7-2 &

In each of formulas (7-1) and (7-2)
R ₇ , R ₈ , R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 6 carbon atoms.
The compound according to claim 2, wherein the compound represented by Formula 4 is represented by Formula 8 below.
(8)

In the above formula (8), Ar ₂ represents any one selected from the following Substituents 1-1 to 1-8,
<Substituent 1-1><Substituent1-2>

<Substituent 1-3><Substituent1-4>

<Substituent 1-5><Substituent1-6>

<Substituent 1-7><Substituent1-8>

Ar ₃ and Ar ₄ each independently represent hydrogen or any one selected from Substituents 2-1 to 2-6,
<Substituent 2-1><Substituent2-2>

<Substituent 2-3><Substituent2-4>

&Lt; Substituent 2-5 >< Substituent 2-6 >

L _a represents a single bond or any one selected from Substituents 3-1 to 3-6,
<Substituent 3-1><Substituent3-2>

<Substituent 3-3><Substituent3-4>

<Substituent 3-5><Substituent3-6>

R ₁ and R ₂ each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group.
The compound according to claim 1, wherein the compound represented by the formula (1)
Is selected from compounds represented by Structural Formulas 1 to 34 below.
<Structure 1> <Structure 2>

<Structure 3> <Structure 4>

<Structure 5> <Structure 6>

<Structure 7> <Structure 8>

<Structure 9>

<Structure 10>

<Structure 11>

<Structure 12>
 

<Structure 13>

 
<Structure 14>

<Structure 15>
 

<Structure 16>

<Structure 17> <Structure 18>

  

<Structure 19>

<Structure 20>

<Structure 21> <Structure 22>

<Structure 23> <Structure 24>

   

<Structure 25> <Structure 26>

  

<Structure 27> <Structure 28>

    

<Structure 29>

  
<Structure 30>

<Structure 31>

 
<Structure 32>

<Structure 33>

<Structure 34>
 

<Structure 35>

<Structure 36>

A first electrode;
A second electrode;
A light emitting layer disposed between the first electrode and the second electrode; And
And a hole transporting layer disposed between the first electrode and the light emitting layer and containing the compound according to any one of claims 1 to 5.
The light emitting device of claim 6, wherein the hole transporting layer further comprises a P-type dopant.
7. The organic electroluminescence device according to claim 6, wherein the hole transporting layer
A first layer comprising said compound and a P-type dopant; And
And a second layer comprising said compound.
An electronic device comprising the light emitting element according to claim 6.
An electronic device according to claim 9, wherein the electronic device is a display device or a lighting device.

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