WO2014046494A1

WO2014046494A1 - Novel compound, and light emitting diode and electronic apparatus comprising same

Info

Publication number: WO2014046494A1
Application number: PCT/KR2013/008465
Authority: WO
Inventors: 최정옥; 정준호; 권오관
Original assignee: 주식회사 엘엠에스
Priority date: 2012-09-21
Filing date: 2013-09-18
Publication date: 2014-03-27

Abstract

From a novel compound, and a light emitting diode and an electronic apparatus comprising same, the novel compound is disclosed.

Description

Novel compounds, light emitting devices and electronic devices comprising the same

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 comprising the same.

In general, a light emitting device includes a light emitting layer including two electrodes facing each other and a light emitting compound interposed between the electrodes. When a current flows 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, and thus can reduce the weight, size or thickness of the display device. In addition, the display device using the light emitting device has an advantage of excellent viewing angle, contrast ratio, color reproducibility, and the like, and lower power consumption than the display device using the backlight and the 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 may stabilize an interface between the anode and the light emitting layer and minimize an energy barrier therebetween.

However, the light emitting device has a short light emitting lifetime and low power efficiency. In order to solve these problems, various compounds have been developed as materials of the light emitting device, but there are limitations in manufacturing a light emitting device that satisfies all of the light emission life, power efficiency and thermal stability.

(Patent Document 1) Japanese Laid-Open Patent No. 2008-294161

(Patent Document 2) Korean Patent Publication No. 2008-0104025

Accordingly, the technical problem of the present invention was conceived in this respect, and an object of the present invention is to provide a novel compound for improving the ability to inject and transport holes in a light emitting device.

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

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

Compound according to an embodiment for realizing the object of the present invention is represented by the following formula (1).

[Formula 1]

In the above formula

L _a and L _b each independently represent * -L ₁ -L ₂ -L ₃ -L _4- *,

L ₁ , L ₂ , L _3, and L ₄ each independently represent a single bond, -O-, -S-, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. A cycloalkylene group having

Ar ₁ and Ar ₂ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, 2 to 20 carbon atoms A heterocycloalkyl group having a bicycloalkyl group having 5 to 20 carbon atoms, the following Chemical Formula 2-1 or the following Chemical Formula 2-2,

[Formula 2-1]

[Formula 2-2]

Het ₁ and Het ₂ each independently represent the following Chemical Formula 3 or the following Chemical Formula 4,

[Formula 3]

[Formula 4]

Where X represents NW, O, S or Si (R ₉ ) (R ₁₀ ),

W is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, carbon atoms A bicycloalkyl group having 5 to 20,

Y represents S or O,

Z represents S,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or A heteroaryl group having 2 to 20 carbon atoms;

l represents an integer of 0 to 3, m, n and o each independently represent an integer of 0 to 4, any one of p and q represents an integer of 0 to 3, and the other represents an integer of 0 to 4, one of r and s represents an integer of 0 to 3, the other represents an integer of 0 to 4,

Substituents represented by Formula 3 are substituted with a compound of Formula 1 at carbon position 1 or 8,

The substituent represented by the formula (4) is substituted with the compound of the formula (1) at the carbon position 3 or 6,

Among the definitions of the substituents described above for Formulas 1 to 4, the alkyl group, aryl group, heteroaryl group, cycloalkyl group, heterocycloalkyl group and bicycloalkyl group are each independently an alkyl group having 1 to 6 carbon atoms and an alkoxy having 1 to 6 carbon atoms Groups, amine groups unsubstituted or substituted with one or more alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 2 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, It is unsubstituted or substituted with one or more substituents selected from the group consisting of 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 hydroxyl group and a carboxy group.

In one embodiment, the compound of Formula 1 may be represented by the formula (5).

[Formula 5]

Where

Ar ₁ , Ar ₂ , L _a , L _b , R ₅ and p are as defined in claim ₁ , Ar ₁ and Ar ₂ are the same as each other, and L _a and L _b are the same as each other.

In another embodiment, the compound of Formula 1 may be represented by the following Formula 6.

[Formula 6]

Where

Ar ₁ , Ar ₂ , L _a , L _b , R ₇ and r are as defined in claim ₁ , Ar ₁ and Ar ₂ are the same as each other, and L _a and L _b are the same as each other.

In another embodiment, the compound of Formula 1 may be represented by the following formula (7).

[Formula 7]

Where

A light emitting device according to an embodiment for realizing another object of the present invention includes a hole transport layer including a first electrode, a second electrode, a light emitting layer and the compound represented by the formula (1). The first electrode and the second electrode may face each other, the emission layer may be interposed between the first and second electrodes, and the hole transport layer may be disposed between the first electrode and the emission layer. .

In one embodiment, the hole transport layer may include 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 of the same type or different from the P-type dopant of the first layer.

According to another aspect of the present disclosure, an electronic device may include a hole transport layer including the compound represented by Chemical Formula 1.

According to such a novel compound, a light emitting device and an electronic device including the same, the novel compound of the present invention can improve the ability to inject and / or transport holes in the light emitting device.

In addition, by using the compound, the light emitting efficiency of the light emitting device may be improved, and the life may 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 for describing a light emitting device according to still 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).

[Formula 1]

In the above formula

L _a and L _b each independently represent * -L ₁ -L ₂ -L ₃ -L _4- *,

[Formula 2-1]

[Formula 2-2]

[Formula 3]

[Formula 4]

Where X represents NW, O, S or Si (R ₉ ) (R ₁₀ ),

Y represents S or O,

Z represents S,

In the present invention, "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, Biphenyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, fluoranthenyl group, fluorenyl group, fluorenyl group Perylenyl group, indenyl group, azulenyl group, azulenyl group, heptalenyl group, phenalenyl group, phenanthrenyl group, and the like. .

The aryl group has 6 to 20 carbon atoms, for example, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.

"Heteroaryl group" refers to an "aromatic heterocycle" derived from a monocyclic or condensed ring. The heteroaryl group, at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si) as a hetero atom, for example, one, two, It can include three or four.

Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group (triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indole Indolyl group, isoindolyl group, indolizinyl group, indolinzinyl group, purinyl group, inindazolyl group, quinolyl group, quinolyl group, isoquinolyl Isoquinolinyl group, quinolizinyl group, phthalazinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group Cinolinyl group, pterididinyl group, imida Zotriazinyl group (imidazotriazinyl group), acridinyl group (acridinyl group), phenanthridinyl group (phenanthridinyl group), carbazolyl group, phenanthrolinyl group (phenanthrolinyl group), phenazinyl group, Nitrogen-containing heteroaryl groups including an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, and the like; Sulfur-containing heteroaryl groups including thienyl group, benzothienyl group, dibenzothienyl group and the like; Furyl group, pyranyl group, cyclopentapyranyl group, cyclopentapyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group and dibenzofuranyl group An oxygen-containing heteroaryl group etc. which are included are mentioned. In addition, specific examples of the heteroaryl group may include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, and a phenothiazinyl group. (phenothiazinyl group), isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, benzoxazolyl group, benzoxazolyl group Compounds containing at least two or more heteroatoms, such as an oxadiazolyl group, a pyrazoloxazolyl group, an imidazothiazolyl group, a thienofuranyl group, and the like have.

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

An "alkyl group" is defined as a functional group derived from linear or branched saturated hydrocarbons.

Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, 1,1-dimethylpropyl group, 1 , 2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2-ethylpropyl group (2 -ethylpropyl group), n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl- 2-methylpropyl group), 1,1,2-trimethylpropyl group (1,1,2-trimethylpropyl group), 1-propylpropyl group (1-propylpropyl group), 1-methylbutyl group (1-methylbutyl group), 2-methylbutyl group, 1,1-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl Group (2,2-dimeth ylbutyl group), 1,3-dimethylbutyl group (1,3-dimethylbutyl group), 2,3-dimethylbutyl group (2,3-dimethylbutyl group), 2-ethylbutyl group (2-ethylbutyl group), 2- Methyl pentyl group (2-methylpentyl group), 3-methylpentyl group, etc. are mentioned.

The alkyl group has 1 to 20 carbon atoms, for example 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.

A "cycloalkyl group" is defined as a functional group derived from a monocyclic saturated hydrocarbon.

Specific examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group (cyclooctyl group) etc. are mentioned.

The cycloalkyl group has 3 to 20 carbon atoms, for example 3 to 12 carbon atoms, or 3 to 6 carbon atoms.

A "heterocycloalkyl group" is defined as a non-aromatic monocyclic or polycyclic group containing at least one heteroatom as a cyclic element in addition to a carbon atom. Heteroatoms may include, but are not limited to, oxygen (O), nitrogen (N), sulfur (S), selenium (Se), or phosphorus (P) atoms. Further, even if the heterocycloalkyl group does not include an aromatic ring, the bond connecting the carbon atom-carbon atom or carbon atom-heteroatom constituting the ring of the heterocycloalkyl group may include a double bond.

Specific examples of the heterocycloalkyl group include 2-pyrrolidinyl group, 3-pyrrolidinyl group, 3-pyrrolidinyl group, piperidinyl group, 2-tetrahydrofuranyl group (2 -tetrahydrofuranyl group, 3-tetrahydrofuranyl group, 2-tetrahydrothienyl group and 3-tetrahydrothienyl group, but are not limited thereto. It is not.

Heterocycloalkyl groups have 2 to 20 carbon atoms, for example 3 to 19 carbon atoms, or 5 to 11 carbon atoms. That is to say that if a heteroatom is included, the heterocycloalkyl group has a ring member of 3 to 21, for example 4 to 20, or 6 to 12.

"Bicycloalkyl group" means a functional group having a structure in which at least one carbon atom selected from each of two alkyl rings is connected to each other.

As a specific example of a bicycloalkyl group, a bicyclopentyl group, a bicyclohexyl group, a bicycloheptyl group, a bicyclootyl group, a bicyclononyl group Or a bicyclodecyl group.

The bicycloalkyl group has 5 to 20 carbon atoms, for example 7 to 18 carbon atoms, or 7 to 12 carbon atoms.

In addition, "arylene group" may mean a divalent substituent derived from the aryl group described above.

In addition, "heteroarylene group" may mean a divalent substituent derived from the heteroaryl group described above.

In the heteroaryl having three rings in the present invention, the position of the carbon atom which may be substituted or substituted is represented as follows based on the hetero atom, and will be described below based on this.

In the above formula, Z represents X of Chemical Formula 2-1, Y of Chemical Formula 3 or Z of Chemical Formula 4.

The abbreviation "Cz" used below refers to carbazole, "DBT" to dibenzothiophene, and "DBF" to dibenzofuran.

In one embodiment of Formula 1,

L _a and L _b each independently represent * -L ₁ -L ₂ -L ₃ -L _4- *,

L ₁ , L ₂ , L ₃ and L ₄ each independently represent a single bond or an arylene group having 6 to 20 carbon atoms,

Ar ₁ and Ar ₂ each independently represent an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, the following Chemical Formula 2-1 or the following Chemical Formula 2-2,

[Formula 2-1]

[Formula 2-2]

[Formula 3]

[Formula 4]

Where X represents NW, O, S or Si (R ₉ ) (R ₁₀ ),

W represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,

Y represents S or O,

Z represents S,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms. ,

m, n, l, o, p, q, r and s may each independently represent an integer of 0 to 2.

In another embodiment of Formula 1,

L _a and L _b each independently represent a single bond or an arylene group having 6 to 20 carbon atoms,

Ar ₁ and Ar ₂ are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; Heteroaryl groups having 2 to 20 carbon atoms which are unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; Formula 2-1 or Formula 2-2,

[Formula 2-1]

[Formula 2-2]

[Formula 3]

[Formula 4]

Where X represents O, S or Si (R ₉ ) (R ₁₀ ),

Y represents S or O,

Z represents S,

m, n, l, o, p and q may each independently represent 0 or 1.

In another embodiment of Formula 1,

L _a and L _b each independently represent a single bond or phenylene,

Ar ₁ and Ar ₂ are each independently a phenyl group unsubstituted or substituted with a methyl group or a phenyl group; Naphthyl group; Or represented by the formula 2-1,

[Formula 2-1]

[Formula 3]

[Formula 4]

Where X represents O, S or Si (R ₉ ) (R ₁₀ ),

Y represents S or O,

Z represents S,

R ₅ and R ₇ each independently represent a methyl group or a phenyl group,

R ₉ and R ₁₀ each independently represent a methyl group,

p and r each independently represent 0 or 1,

l, m, q and s may each independently represent 0.

The compound of Formula 1 may be represented by the following Formula 5, Formula 6 or Formula 7.

[Formula 5]

Where

Ar ₁ , Ar ₂ , L _a , L _b , R ₅ and p are as defined above,

Ar ₁ and Ar ₂ are the same as each other, and L _a and L _b are the same as each other.

[Formula 6]

Where

Ar ₁ , Ar ₂ , L _a , L _b , R ₇ and r are as defined above,

[Formula 7]

Where

Ar ₁ , Ar ₂ , L _a , L _b , R ₅ and p are as defined above,

Specific examples of the compound represented by Formula 5 include compounds represented by the following structures A-1 to A-18.

[Structure A-1]

[Structure A-2]

Structure A-3

Structure A-4

[Structure A-5]

[Structure A-6]

[Structure A-7]

[Structure A-8]

Structure A-9

[Structure A-10]

Structure A-11

[Frame A-12]

Structure A-13

[Frame A-14]

[Frame A-15]

[Structure A-16]

[Structure A-17]

[Frame A-18]

Specific examples of the compound represented by the formula (6) include compounds represented by the following structures B-1 to B-11.

[Structure B-1]

[Structure B-2]

[Structure B-3]

[Structure B-4]

[Structure B-5]

[Structure B-6]

[Structure B-7]

[Structure B-8]

[Structure B-9]

[Structure B-10]

[Structure B-11]

Specific examples of the compound represented by Formula 7 include compounds represented by the following structures C-1 to C-10.

[Structure C-1]

[Structure C-2]

Structure C-3

[Structure C-4]

[Structure C-5]

[Structure C-6]

[Structure C-7]

[Structure C-8]

[Structure C-9]

[Structure C-10]

Hereinafter, a light emitting device including the 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.

Referring to FIG. 1, the 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 the 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. In this case, the first electrode 20 may be formed of indium tin oxide (ITO). Alternatively, the first electrode 20 may be an opaque (reflective) electrode. In this case, 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 transport 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 transport layer 30 includes a compound represented by the following Chemical Formula 1 as a hole transport compound.

[Formula 1]

The compound represented by the said Formula (1) is substantially the same as what was demonstrated above as a novel compound which concerns on this invention. Therefore, detailed description of Ar ₁ , Ar ₂ , L _a , L _b , Het ₁ and Het ₂ 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 with a conductive material. When the first electrode 20 is a transparent electrode, the second electrode 50 may be an opaque (reflective) electrode. In this case, the second electrode 50 may be an aluminum electrode. On the contrary, when the first electrode 20 is an opaque electrode, the second electrode 50 may be a transparent or semi-transparent electrode, and the second electrode 50 may have a thickness of 100 μs to 150 μs. And an alloy containing 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 between the emission layer 40 and the second electrode 50 as an electron transport layer.

When a current flows between the first and

second electrodes

20 and 50 of the light emitting device 100, holes and holes injected from the first electrode 20 into the light emitting layer 40 are formed. Electrons injected into the emission layer 40 from the second electrode 50 combine to form excitons. In the process of transferring the excitons to the ground state, light having a wavelength in a specific region is generated. In this case, the excitons may be singlet excitons, and may also be triplet excitons. Accordingly, the light emitting device 100 may provide light to the outside.

Although not shown in the drawings, 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. It may further include. The electron transport layer and the electron injection layer may be sequentially stacked on the light emitting layer 40.

In addition, 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 / or the light emitting layer 40 and the second electrode 50. It may further include a second blocking layer (not shown) disposed between.

For example, the first blocking layer is disposed between the hole transport layer 30 and the light emitting layer 40, and electrons injected from the second electrode 50 pass through the light emitting layer 40. It may be an electron blocking layer (EBL) that prevents the inflow into the transport layer 30. In addition, the first blocking layer may be an exciton blocking layer that prevents excitons formed in the light emitting layer 40 to diffuse in the direction of the first electrode 20 to prevent the excitons from extinction. In addition, the first blocking layer may be an exciton dissociation blocking layer (EDBL). The exciton separation blocking layer may prevent the exciton formed in the light emitting layer 40 from undergoing non-luminescence extinction through an exciton dissociation process at an interface between the light emitting layer 40 and the hole transporting layer 30. have. In order to prevent exciton separation at the interface, the compound forming the first blocking layer may be selected to have a similar level of HOMO value as the compound forming the light emitting layer 40.

In this case, the first blocking 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, the light emitting layer 40 and the electron transporting layer so that holes are formed from the first electrode 20 to the light emitting layer 40. It may be a hole blocking layer (HBL) to prevent the flow into the electron transport layer via). In addition, the second blocking layer may be an exciton blocking layer which prevents excitons formed in the emission layer 40 from diffusing in the direction of the second electrode 50 to prevent the excitons from extinction.

Adjusting the thickness of each of the first and second blocking layers according to the resonance length of the light emitting device 100 may increase the light emission efficiency and adjust the excitons to be formed at the center of the light emitting layer 40. Can be.

Referring to FIG. 2, the light emitting device 102 includes a first electrode 20, a hole transport layer 32, a light emitting layer 40, and a second electrode 50 formed on the base substrate 10. Except for the hole transport layer 32, the description thereof is substantially the same as that described with reference to FIG.

The hole transport layer 32 includes a compound represented by Chemical Formula 1 and a P-type dopant. Since the compound included in the hole transport layer 32 is substantially the same as described above, overlapping detailed description thereof will be omitted.

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

Specific examples of the P-type organic dopant include compounds represented by the following Chemical Formulas 8 to 12, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanonaphtho-2,6-quinomimethane (11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane (3, 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ) or Tetracyanoquinodimethane (TCNQ) and the like. These may be used alone or in combination of two or more, respectively.

[Formula 8]

In Formula 8, R may represent a cyano group, a sulfone group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group, or a trifluoromethyl group.

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formula 12, m and n may each independently represent an integer of 1 to 5, and Y ₁ and Y ₂ may each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms. . At this time, in Formula 12, the 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 hydroxyl group, and substituted with Alternatively, unsubstituted hydrogen of Y ₁ and Y ₂ may be each independently substituted or unsubstituted with a halogen group.

For example, the compound represented by Chemical Formula 12 may include a compound represented by Chemical Formula 12a or Chemical Formula 12b.

[Formula 12a]

[Formula 12b]

Examples of the P-type inorganic dopant include metal oxides and metal halides. Specific examples of the P-type inorganic 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 , MgF ₂ , and the like. . These may be used alone or in combination of two or more, respectively.

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 parts by weight to about 15 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. Alternatively, the P-type dopant may be about 1 part by weight to 10 parts by weight, 1 part by weight to 5 parts by weight, 1.5 parts by weight to 6 parts by weight, or 2 parts by weight to 5 parts by weight, based on 100 parts by weight of the hole transporting compound. Can be.

When the content of the P-type dopant is about 0.5 part by weight to about 20 parts by weight with respect to 100 parts by weight of the hole transporting compound, the P-type dopant may generate excessive leakage current without reducing the physical properties of the hole-transporting compound. You can prevent it. In addition, the energy barrier at the interface with each of the upper and lower layers in contact with the hole transport layer 32 may be reduced by the P-type dopant.

Although not illustrated in the drawings, 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 illustrated in FIG. 1 may further include an interlayer (not shown). The intermediate layer may be disposed between the first electrode 20 and the hole transport layer 30 of FIG. 1, and may be formed of a compound used as the P-type dopant described with reference to FIG. 2.

Referring to FIG. 3, the light emitting device 104 includes a first electrode 20, a hole transport layer 34, a light emitting layer 40, and a second electrode 50 formed on the base substrate 10. Except for the hole transport layer 34, the description thereof is substantially the same as that described with reference to FIG.

The hole transport 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 transport layer 34 may have a two-layer structure. In addition, the hole transport 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 transport compound. By making the components of the hole transporting compound included in the first layer 33a and the second layer 33b the same, physicochemical defects that may occur at the interface between different materials are reduced, thereby easily injecting holes into the light emitting layer. It can be done. In another aspect, when the same host material is used for the first layer 33a and the second layer 33b, the first layer 33a and the second layer 33b can be continuously formed in one chamber. There is an advantage that the manufacturing process is simplified and the production time can be shortened. Furthermore, since physical properties such as glass transition temperature between adjacent layers become similar, there is an advantage of increasing durability of the device.

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

The second layer 33b includes the novel compound according to the present invention represented by Chemical Formula 1 as a hole transporting compound, and the hole transporting compound constituting the second layer 33b is formed of the first layer 33a. It may be the same as the hole transporting compound constituting. Since the second layer 33b is also substantially the same as the hole transport layer 30 described with reference to FIG. 1 except for the thickness, detailed descriptions thereof will be omitted.

Alternatively, the first and second layers 33a and 33b may include different kinds of hole transport compounds. The hole transporting compound constituting the first and second layers 33a and 33b may be a novel compound according to the present invention represented by Chemical Formula 1, wherein Ar ₁ , Ar ₂ , L _a , L _b , Het ₁ and Het ₂ may be different from each other independently. In this case, 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 transport compound. In this case, the types of P-type dopants doped in the first layer 33a and the second layer 33b may be different from each other, and the doping amount may be different even if the same type 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 are represented by Equation 1 below. Can be satisfied.

[Equation 1]

P1 / P2 ≥ 1

In Equation 1,

In Equation 1, “P1” is a content of a doped P-type dopant relative to 100 parts by weight of the hole transporting compound in the first layer 33a, and “P2” is a hole transporting compound 100 in the second layer 33b. The amount of doped P-type dopant to weight part.

For example, the content of the P-type dopant doped in the first layer 33a is 0.3 to 20 parts by weight, 1 to 15 parts by weight, 2 to 10 parts by weight, or 4 based on 100 parts by weight of the hole transporting compound. To 6 parts by weight. In addition, 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 transporting compound. It may be a minor range.

In addition, although not shown in the drawings, 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.

Since each of the

light emitting devices

100, 102, 104 described above includes the novel compound according to the present invention represented by Chemical Formula 1, the

light emitting devices

100, 102, 104 have excellent thermal stability and At the same time, the luminous efficiency can be improved and the life can be long.

1 to 3, the

light emitting devices

100, 102, 104 are directly formed on the base substrate 10, but the first and second

light emitting devices

100, 102, and 104 are respectively formed on the base substrate 10. A thin film transistor may be disposed between the first electrode 20 and the base substrate 10 as a driving element for driving a pixel. In this case, 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 electrode 20 is disposed separately from each other in the plurality of pixels, and the base substrate 10 is disposed along an edge of the first electrode 20. The barrier rib pattern may be formed so that layers stacked on the first electrode 20 disposed in adjacent pixels may be separated 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.

In addition, the

light emitting devices

100, 102, and 104 may be used as lighting devices.

As such, the

light emitting devices

100, 102, 104 illustrated in the present invention may 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 through specific examples according to the present invention. The embodiments exemplified below are only for the detailed description of the present invention, and are not intended to limit the scope of the rights.

실시예 1Example 1

1 L three-necked round bottom flask was charged with nitrogen, followed by Compound Aa (37.6 mmol, 20.0 g), Compound Ab (41.3 mmol, 23.9 g), 200 mL tetrahydrofuran (THF) and ethanol (EtOH) 100 ㎖ was added and stirred for 30 minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (150.2 mmol, 20.8 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Subsequently, tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.80 mmol, 0.87 g) was added to the 1 L three neck round bottom flask, followed by It was refluxed for time. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 20 minutes, and filtered to give 27.2 g of a light gray solid, Compound 1. Obtained (yield 80%).

MALDI-TOF: m / z = 904.3319 (C ₆₄ H ₄₄ N ₂ S ₂ = 904.29)

실시예 2Example 2

Into a 1 L three-necked round bottom flask with nitrogen, Compound Ba (39.6 mmol, 20.0 g), Compound Bb (43.6 mmol, 24.1 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (158.4 mmol, 21.9 g) was dissolved in 100 mL of water (H ₂ O) and then added to the 1 L three neck round bottom flask. Subsequently, tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (1.54 mmol, 1.8 g) was added to the 1 L three neck round bottom flask, followed by blocking light and reflux for 5 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 27.6 g of a light gray solid. Obtained (yield 82%).

MALDI-TOF: m / z = 848.2319 (C ₆₀ H ₃₆ N ₂ S ₂ = 848.23)

실시예 3Example 3

1 L three-necked round bottom flask was charged with nitrogen, followed by compound Ca (30.5 mmol, 20.0 g), compound Cb (33.5 mmol, 23.6 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (121.8 mmol, 16.8 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Subsequently, tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.6 mmol, 0.7 g) was added to the 1 L three neck round bottom flask, then shielded from light and reflux for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 1 hour, and filtered to give 28.5 g of compound 3 as a light gray solid. Obtained (yield 81%).

MALDI-TOF: m / z = 1152.5292 (C ₈₄ H ₅₂ N ₂ S ₂ = 1152.36)

실시예 4Example 4

Into a 1 L three-necked round bottom flask with nitrogen, Compound Da (36.1 mmol, 20.0 g), Compound Db (39.7 mmol, 23.9 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (144.3 mmol, 19.9 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 4 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 20 minutes, and filtered to give 27.5 g of a light gray solid. Obtained (yield 79%).

MALDI-TOF: m / z = 948.5489 (C ₆₈ H ₄₀ N ₂ S ₂ = 948.26)

실시예 5Example 5

Into a 1 L three-necked round bottom flask with nitrogen, Compound Ea (37.6 mmol, 20.0 g), Compound Eb (41.3 mmol, 24.0 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (150.2 mmol, 20.8 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.8 mmol, 0.9 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 7 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 28.2 g of a light gray solid. Obtained (yield 83%).

MALDI-TOF: m / z = 904.6587 (C ₆₄ H ₄₄ N ₂ S ₂ = 904.29)

실시예 6Example 6

After filling with a 1 L three-necked round bottom flask with nitrogen, Compound Fa (39.6 mmol, 20.0 g), Compound Fb (43.6 mmol, 24.0 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (158.6 mmol, 21.9 g) was dissolved in 100 mL of water (H ₂ O) and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.8 mmol, 0.9 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 20 minutes, and filtered to obtain 26.9 g of a light gray solid. Obtained (yield 80%).

MALDI-TOF: m / z = 848.2637 (C ₆₀ H ₃₆ N ₂ S ₂ = 848.23)

실시예 7Example 7

1 L three-necked round bottom flask was charged with nitrogen, followed by compound Ga (41.0 mmol, 20.0 g), compound Gb (45.0 mmol, 24.1 g), 200 mL of tetrahydrofuran (THF) and 100 mL of ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (163.8 mmol, 22.6 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.8 mmol, 1.0 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 5 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 40 minutes, and filtered to obtain 27.8 g of a light gray solid. Obtained (yield 83%).

MALDI-TOF: m / z = 816.6564 (C ₆₀ H ₃₆ N ₂ O ₂ = 816.28)

실시예 8Example 8

Into a 1 L three-necked round bottom flask with nitrogen, Compound H (32.8 mmol, 20.0 g), Compound Hb (36.0 mmol, 23.7 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (131.0 mmol, 18.1 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 10 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 1 hour, and filtered to give compound 8, a light gray solid, 27.1. g was obtained (yield 78%).

MALDI-TOF: m / z = 1060.1911 (C ₇₂ H ₄₀ N ₂ S ₄ = 1060.21)

실시예 9Example 9

Into a 1 L three-necked round bottom flask with nitrogen, add compound Ia (33.6 mmol, 20.0 g), compound Ib (37.0 mmol, 23.7 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (134.6 mmol, 18.6 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), added to 1 L of methanol, stirred for 30 minutes, and filtered to give 27.7 g of a light gray solid. Obtained (yield 80%).

MALDI-TOF: m / z = 1029.2425 (C ₇₂ H ₄₀ N ₂ O ₂ S ₂ = 1028.25)

실시예 10Example 10

Into a 1 L three-necked round bottom flask with nitrogen, Compound Ja (33.6 mmol, 20.0 g), Compound Jb (37.0 mmol, 23.7 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (134.6 mmol, 18.6 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 9 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 20 minutes, and filtered to give 28.0 g of a light gray solid. Obtained (yield 81%).

MALDI-TOF: m / z = 1029.3885 (C ₇₂ H ₄₀ N ₂ O ₂ S ₂ = 1028.25)

실시예 11Example 11

Into a 1 L three-necked round bottom flask with nitrogen, Compound Ka (34.6 mmol, 20.0 g), Compound Kb (38.0 mmol, 23.8 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (138.3 mmol, 19.1 g) was dissolved in 100 mL of water (H ₂ O) and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 28.3 g of a light gray solid. Obtained (yield 82%).

MALDI-TOF: m / z = 996.3124 (C ₇₂ H ₄₀ N ₂ O ₄ = 996.30)

실시예 12Example 12

Into a 1 L three-necked round bottom flask with nitrogen, Compound La (27.5 mmol, 20.0 g), Compound Lb (30.3 mmol, 23.4 g), 200 mL of tetrahydrofuran (THF) and 100 mL of ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (110.1 mmol, 15.2 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 40 minutes, and filtered to obtain 27.8 g of a compound 12 as a light gray solid. Obtained (yield 78%).

MALDI-TOF: m / z = 1292.4312 (C ₉₀ H ₆₄ N ₂ S ₂ Si ₂ = 1292.40)

실시예 13Example 13

Into a 1 L three-necked round bottom flask with nitrogen, Compound Ma (34.5 mmol, 20.0 g), Compound Mb (37.9 mmol, 23.8 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (137.8 mmol, 19.0 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 20 minutes, and filtered to give 27.9 g of a compound 13 as a light gray solid. Obtained (yield 81%).

MALDI-TOF: m / z = 1000.6598 (C ₇₂ H ₄₄ N ₂ S ₂ = 1000.29)

실시예 14Example 14

Into a 1 L three necked round bottom flask, nitrogen was charged, followed by compound Na (34.5 mmol, 20.0 g), compound Nb (37.9 mmol, 23.8 g), 200 mL tetrahydrofuran (THF), and 100 mL ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (137.8 mmol, 19.0 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 27.6 g of a compound 14 as a light gray solid. Obtained (yield 80%).

MALDI-TOF: m / z = 1000.5798 (C ₇₂ H ₄₄ N ₂ S ₂ = 1000.29)

비교예 1Comparative Example 1

Charge 1 L three-necked round bottom flask with nitrogen, add Compound A (67.4 mmol, 34.0 g), Compound B (74.1 mmol, 40.9 g), 340 mL of tetrahydrofuran (THF) and 170 mL of ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (269.6 mmol, 37.3 g) was dissolved in 170 mL of water (H ₂ O) and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (2.7 mmol, 3.1 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 170 mL of tetrahydrofuran (THF), poured into 1,700 mL of methanol (methanol), filtered for 20 minutes, filtered, and light gray. 40.1 g of Comparative Compound 1 was obtained as a solid (yield 70%).

MALDI-TOF: m / z = 848.2359 (C ₆₀ H ₃₆ N ₂ S ₂ = 848.23)

비교예 2Comparative Example 2

Into a 1 L three-necked round bottom flask with nitrogen, add Compound C (41.0 mmol, 20.0 g), Compound D (45.0 mmol, 24.1 g), 200 mL tetrahydrofuran (THF) and 100 mL ethanol (EtOH). Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (163.8 mmol, 22.6 g) was dissolved in 100 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (1.6 mmol, 1.9 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1000 mL of methanol, stirred for 20 minutes and filtered to obtain a Comparative Compound 2 as a light gray solid. 23.4 g were obtained (yield 70%).

MALDI-TOF: m / z = 816.2810 (C ₆₀ H ₃₆ N ₂ O ₂ = 816.28)

비교예 3Comparative Example 3

Into a 1 L three-necked round bottom flask with nitrogen, Compound E (15.9 mmol, 8.0 g), Compound F (17.4 mmol, 9.6 g), 80 mL of tetrahydrofuran (THF) and 40 mL of ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (63.4 mmol, 8.8 g) was dissolved in 40 mL of water (H ₂ O) and then added to the 1 L three neck round bottom flask. Tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (0.6 mmol, 0.7 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 40 mL of tetrahydrofuran (THF), poured into 400 mL of methanol, stirred for 20 minutes, and filtered to obtain a Comparative Compound 3 as a light gray solid. 11.4 g were obtained (yield 85%).

MALDI-TOF: m / z = 848.2353 (C ₆₀ H ₃₆ N ₂ S ₂ = 848.23)

비교예 4Comparative Example 4

After filling with a 1 L three necked round bottom flask with nitrogen, Compound G (61.4 mmol, 30.0 g), Compound H (67.6 mmol, 36.2 g), 300 mL of tetrahydrofuran (THF) and 150 mL of ethanol (EtOH) were added. Stir for minutes. In addition, potassium carbonate (K ₂ CO ₃ ) (245.7 mmol, 34.0 g) was dissolved in 150 mL of water (H ₂ O), and then added to the 1 L three neck round bottom flask. Subsequently, tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) (2.5 mmol, 2.8 g) was added to the 1 L three neck round bottom flask, followed by blocking light and reflux for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 150 mL of tetrahydrofuran (THF), poured into 1,500 mL of methanol, stirred for 20 minutes and filtered to obtain a light gray solid. 35.1 g were obtained (yield 70%).

MALDI-TOF: m / z = 816.2834 (C ₆₀ H ₃₆ N ₂ O ₂ = 816.28)

비교예 5Comparative Example 5

The following compounds were prepared according to the synthesis method disclosed in Japanese Patent Laid-Open No. 2012-175025.

비교예 6Comparative Example 6

The following compounds were prepared according to the synthesis method disclosed in WO12 / 008281.

비교예 7Comparative Example 7

The following compound was prepared according to the synthesis method disclosed in JP 2012-049518 A.

비교예 8Comparative Example 8

비교예 9 내지 12Comparative Examples 9 to 12

Compounds having the structures of Formulas a, b, c and d were obtained commercially and prepared, and used in Comparative Examples 9 to 12, respectively.

[Formula a]

[Formula b]

[Formula c]

[Formula d]

Manufacturing of Light Emitting Diodes A-1 to A-4

On the first electrode formed of indium tin oxide (ITO), the compound according to Example 1 was deposited as a host material at a rate of 1 Å / sec and simultaneously represented by the following P-type dopant (HAT-CN) Was co-evaporated at a ratio of about 5 parts by weight to 100 parts by weight of the host material to form a first layer having a thickness of 100 mm 3. The compound according to Example 1 was deposited on the first layer to a thickness of 300 mm 3 to form a second layer.

MCBP represented by Chemical Formula 14 and Ir (ppy) ₃ represented by Chemical Formula 15 were co-deposited on the second layer at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 300 GPa. Deposition formed a blocking layer.

Then, BPhen represented by the following formula (16) and Alq ₃ represented by the following formula (17) were co-deposited on the blocking layer in a 50:50 weight ratio to form an electron transport layer having a thickness of about 400 GPa. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by 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 Å was formed.

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

In the above method, a green light emitting device A-1 including the compound according to Example 1 of the present invention was prepared.

Further, except that the host material is formed using the compounds according to Examples 3, 4, and 8, respectively, to form the first layer and the second layer, the process of manufacturing the light emitting device A-1 is substantially the same. Through the same process to produce a light emitting device A-2 to A-4.

Preparation of Comparative Elements 1-4

Substantially the same as the process of manufacturing the light emitting device A-1, except for forming the first layer and the second layer using a compound according to Comparative Examples 9 to 12 represented by the formula (a) to (d) Comparative elements 1 to 4 were manufactured through the process.

Evaluation of power efficiency and lifespan of light emitting device -1

For each of the light emitting elements A-1 to A-4 and the comparative elements 1 to 4 according to the present invention, after dispensing the sealant for UV curing on the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere, Each of the light emitting elements and the comparative elements and the cover glass were bonded to each other and cured by irradiating UV light. For each of Light-Emitting Elements A-1 to A-4 and Comparative Elements 1 to 4 prepared as described above, power efficiency was measured based on the value when luminance was 500 cd / m ² . The results are shown in Table 1.

In addition, the lifetimes of each of the light emitting elements A-1 to A-4 and the comparative elements 1 to 4 were measured using a life meter installed in a measuring oven maintained at a constant temperature of about 85 ° C. The results are shown in Table 1.

In Table 1, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 1, T ₇₅ means a time taken for the luminance of the light emitting device to be 75% of the initial luminance when the initial luminance of the light emitting device is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

Table 1

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element A-1	32.1	832
Light emitting element A-2	31.4	812
Light emitting element A-3	30.6	791
Light emitting element A-4	30.8	783
Comparative element 1	9.2	227
Comparative element 2	10.3	234
Comparative element 3	9.5	244
Comparative element 4	8.5	225

Referring to Table 1, it can be seen that the power efficiency of the light emitting elements A-1 to A-4 is about 32.1 lm / W, about 31.4 lm / W, about 30.6 lm / W, and about 30.8 lm / W, respectively. That is, it can be seen that the power efficiency of each of the light emitting devices manufactured using the compounds according to Examples 1, 3, 4, and 8 of the present invention is at least about 30.0 lm / W or more. On the other hand, since the power efficiency of the comparative devices 1 to 4 is about 8.5 lm / W to about 10.3 lm / W, the power efficiency of the light emitting devices manufactured using the compounds according to an embodiment of the present invention is the power of the comparative devices It can be seen that better than the efficiency.

In addition, the lifespan of each of the light emitting devices manufactured using the compounds according to the embodiment of the present invention is at least about 783 hours, compared to the life of the comparative elements 1 to 4 of about 244 hours or less, It can be seen that the lifespan of the light emitting devices including the compound according to the present invention is better than that of the comparative devices 1 to 4.

In addition, considering that the life characteristic evaluation of the light emitting device was performed under an acceleration condition (severe condition) of 85 ° C., the life characteristics of the light emitting devices including the compound according to the embodiment of the present invention are superior to those of the comparative devices 1 to 4. Through it can be seen that the heat resistance of the light emitting device manufactured using the compound according to the present invention is superior to the comparative devices 1 to 4.

Manufacturing of Light Emitting Diodes B-1 to B-4

On the first electrode formed of indium tin oxide (ITO), a P-type dopant (HAT-CN) represented by Formula 13 was deposited to a thickness of about 100 GPa to form a first layer, and the first layer NPB (N, N'-diphenyl-N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'-diamine) was deposited to a thickness of about 300 kPa on the second layer to form a second layer. It was.

On the second layer, a first blocking layer having a thickness of about 100 μs is formed with the compound according to Example 1, and on the first blocking layer, mCBP represented by Formula 14 and Ir (ppy) ₃ represented by Formula 15 Was co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 300 mW, and mCBP was deposited to a thickness of about 50 mW again on the light emitting layer to form a second blocking layer.

Then, BPhen represented by Formula 16 and Alq ₃ represented by Formula 17 were co-deposited at a 50:50 weight ratio on the second blocking layer to form an electron transport layer having a thickness of about 400 μm. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by using Liq represented by Formula 18.

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

Except for manufacturing the first blocking layer using each of the compounds according to Examples 3, 4 and 8 of the present invention, the light emitting device through substantially the same process as the manufacturing process of the light emitting device B-1 B-2, B-3 and B-4 were prepared.

Preparation of Comparative Elements 5 and 6

Comparative element 5 was manufactured through the same process as that of manufacturing light emitting device B-1, except that the first blocking layer was manufactured using the compound according to Comparative Example 10 represented by Chemical Formula b. .

Further, except that the first blocking layer is manufactured using the compound according to Comparative Example 11 represented by Chemical Formula c, Comparative Device 6 is manufactured by substantially the same process as the process of manufacturing Light-Emitting Device B-1. Prepared.

Evaluation of power efficiency and lifespan of light emitting device -2

For the light emitting elements B-1 to B-4 and the comparative elements 5 and 6 according to the present invention prepared as described above, in the same manner as the power efficiency measurement experiments for the light emitting elements A-1 to A-4, respectively. , Power efficiency was measured based on the value when the luminance was 500 cd / m ² .

In addition, the lifespans of the light emitting elements B-1 to B-4 and the comparative elements 5 and 6 were measured in substantially the same manner as the life evaluation experiments for the light emitting elements A-1 to A-4.

Table 2 shows the results of power efficiency and lifespan of the light emitting elements B-1 to B-4 and Comparative elements 5 and 6, respectively. In Table 2, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 2, T ₇₅ means the time taken for the luminance of the light emitting element to be 75% of the initial luminance when the initial luminance of the light emitting element is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

TABLE 2

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element B-1	34.9	714
Light emitting element B-2	34.7	681
Light emitting element B-3	33.1	664
Light emitting element B-4	33.5	656
Comparative element 5	11.2	212
Comparative element 6	12.5	218

Referring to Table 2, the power efficiency of each of the light emitting devices B-1 to B-4 manufactured using the compounds according to the present invention was about 34.9 lm / W, about 34.7 lm / W, about 33.1 lm / W and about 33.5 As lm / W, at least about 33.1 lm / W or more, while the power efficiency of Comparative Element 5 is only about 11.2 lm / W and the power efficiency of Comparative Element 6 is only about 12.5 lm / W.

In addition, the lifespan of each of the light emitting elements B-1 to B-4 is at least about 656 hours, whereby the lifetime of the comparative element 5 is about 212 hours and the lifetime of the comparative element 6 is about 218 hours, the compound according to the invention It can be seen that the lifespan of the light emitting devices manufactured using the light emitting diodes is relatively longer than those of the comparative devices 5 and 6.

In addition, considering that the life characteristic evaluation of the light emitting device was performed under an accelerated condition (severe condition) of 85 ° C., the life characteristics of the light emitting device including the compound according to the present invention were longer than those of the comparative devices 5 and 6. It can be seen that the heat resistance of the light emitting device manufactured using the compound according to the invention is excellent.

Manufacturing of Light Emitting Diodes C-1 to C-4

On the first electrode formed of indium tin oxide (ITO), NPB is deposited as a host material at a rate of 1 μs / sec and simultaneously a P-type dopant (HAT-CN) represented by Chemical Formula 13 is deposited on the host material 100. Co-evaporation was performed at a ratio of about 5 parts by weight to parts by weight to form a 100 mm thick first layer. NPB was deposited to a thickness of 300 Å on the first layer to form a second layer. Forming a first blocking layer having a thickness of about 100 μs with a compound according to Example 1 on the second layer, mCBP represented by the formula (14) and Ir (ppy) ₃ represented by the formula (15) on the first blocking layer Co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 300 kPa, and mCBP was deposited to a thickness of about 50 kPa on the light emitting layer to form a second blocking layer.

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

Except for manufacturing the first blocking layer using each of the compounds according to Examples 5, 6 and 9 of the present invention, the light emitting device through the substantially same process as the manufacturing process of the light emitting device C-1 C-2, C-3 and C-4 were prepared.

Preparation of Comparative Elements 7 and 8

Comparative element 7 was manufactured by the same process as that of manufacturing light emitting device C-1, except that the first blocking layer was manufactured using the compound according to Comparative Example 10 represented by Chemical Formula b. .

Comparative device 8 was manufactured through the same process as that of manufacturing light emitting device C-1, except that the first blocking layer was manufactured using the compound according to Comparative Example 11 represented by Chemical Formula c. .

Evaluation of Power Efficiency and Lifespan of Light-Emitting Element -3

For each of the light emitting elements C-1 to C-4 and the comparative elements 7 and 8 prepared as described above, the luminance was 500 cd in substantially the same manner as the power efficiency measurement experiment for the light emitting elements A-1 to A-4. The power efficiency was measured based on the value at / m ² .

In addition, the lifespans of the light emitting elements C-1 to C-4 and the comparative elements 7 and 8 were measured in substantially the same manner as the life evaluation experiments for the light emitting elements A-1 to A-4.

Table 3 shows the results of power efficiency and lifespan of the light emitting elements C-1 to C-4 and the comparative elements 7 and 8, respectively. In Table 3, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 3, T ₇₅ means the time taken for the luminance of the light emitting element to be 75% of the initial luminance when the initial luminance of the light emitting element is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

TABLE 3

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element C-1	36.1	739
Light emitting element C-2	32.3	734
Light emitting element c-3	31.2	656
Light emitting element C-4	30.1	633
Comparative element 7	12.6	218
Comparative element 8	13.1	220

Referring to Table 3, the power efficiency of each of the light emitting devices C-1 to C-4 is about 36.1 lm / W, about 32.3 lm / W, about 31.2 lm / W and about 30.1 lm / W, It can be seen that the power efficiency is only about 12.6 lm / W and that of Comparative Device 8 is only about 13.1 lm / W. Accordingly, it can be seen that the power efficiency of the light emitting devices including the compound according to the present invention is better than that of the comparative devices 7 and 8.

In addition, the lifespan of each of the light emitting elements C-1 to C-4 is about 739 hours, about 734 hours, about 656 hours, and about 633 hours, whereas the lifetime of the comparative element 7 is only about 218 hours and the lifetime of the comparative element 8 It can be seen that only about 220 hours. Therefore, it can be seen that the lifespan of the light emitting devices including the compound according to the present invention is longer than that of the comparative devices 7 and 8.

In addition, considering that the life characteristic evaluation of the light emitting device is performed under an acceleration condition (severe condition) of 85 ° C., the life characteristics of the light emitting device including the compound according to the present invention are superior to those of the comparative devices 7 and 8, It can be seen that the heat resistance of the light emitting device manufactured using the compound according to the present invention is good.

Manufacturing of Light Emitting Diodes D-1 to D-4

On the first electrode formed of indium tin oxide (ITO), the compound according to Example 1 is deposited as a host material at a rate of 1 Å / sec and simultaneously is a P-type dopant represented by Chemical Formula 13 (HAT-CN). Was co-evaporated at a ratio of about 5 parts by weight to 100 parts by weight of the host material to form a first layer having a thickness of 100 mm 3. NPB was deposited to a thickness of 300 Å on the first layer to form a second layer. MCBP represented by Chemical Formula 14 and Ir (ppy) ₃ represented by Chemical Formula 15 were co-deposited on the second layer at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 300 GPa, and mCBP was about 50 kV on the light emitting layer. The thickness was deposited to form a barrier layer.

Then, BPhen represented by Chemical Formula 16 and Alq ₃ represented by Chemical Formula 17 were co-deposited on the blocking layer in a 50:50 weight ratio to form an electron transport layer having a thickness of about 400 μm. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by using Liq represented by Formula 18.

On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture a green light emitting device D-1 including the compound according to Example 1 of the present invention.

Except for manufacturing the first layer using each of the compounds according to Examples 3, 4 and 8 of the present invention, the light emitting device D through substantially the same process as the manufacturing process of the light emitting device D-1 -2, D-3 and D-4 were prepared.

Preparation of Comparative Elements 9 and 10

Comparing device 9 is carried out through substantially the same process as manufacturing light emitting device D-1, except that the host material of the first layer is manufactured using the compound according to Comparative Example 10 represented by Chemical Formula b. Prepared.

Comparative device 10 is manufactured through the substantially same process as that of manufacturing light emitting device D-1, except that the host material of the first layer is manufactured using the compound according to Comparative Example 11 represented by Chemical Formula c. Prepared.

Evaluation of power efficiency and lifespan of light emitting device -4

For each of the light emitting elements D-1 to D-4 and the comparative elements 9 and 10 prepared as described above, the luminance was 500 cd in substantially the same manner as the power efficiency measurement experiments for the light emitting elements A-1 to A-4. The power efficiency was measured based on the value at / m ² .

In addition, the lifetimes of the light emitting elements D-1 to D-4 and the comparative elements 9 and 10 were measured in substantially the same manner as the life evaluation experiments for the light emitting elements A-1 to A-4.

Table 4 shows the results of power efficiency and lifespan of the light emitting elements D-1 to D-4 and the comparative elements 9 and 10, respectively. In Table 4, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 4, T ₇₅ means the time taken for the luminance of the light emitting device to be 75% of the initial luminance when the initial luminance of the light emitting device is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

Table 4

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element d-1	30.7	760
Light emitting element d-2	30.5	731
Light emitting element d-3	29.1	715
Light emitting element D-4	29.5	707
Comparative element 9	9.3	202
Comparative element 10	8.9	193

Referring to Table 4, the power efficiency of each of the light emitting elements D-1 to D-4 is at least about 29.1 lm / W or more, while the power efficiency of the comparative element 9 is only about 9.3 lm / W and the power efficiency of the comparative element 10. It can be seen that is only 8.9 lm / W. Accordingly, it can be seen that the power efficiency of the light emitting devices using the compound according to the present invention is superior to that of the comparative devices 9 and 10.

In addition, the lifespan of each of the light emitting elements D-1 to D-4 is at least about 707 hours, whereas the lifespan of the comparative element 9 is only about 202 hours, and the lifetime of the comparative element 10 is only about 193 hours. . Accordingly, it can be seen that the lifetimes of the light emitting devices using the compound according to the present invention are longer than those of the comparative devices 9 and 10.

In addition, considering that the life characteristic evaluation of the light emitting device was performed under an acceleration condition (severe condition) of 85 ° C., the life characteristics of the light emitting device including the compound according to the present invention were superior to those of the comparative devices 9 and 10, It can be seen that the light emitting device manufactured using the compound according to the present invention has good heat resistance.

Manufacturing of Light Emitting Diodes E-1 to E-4

On the first electrode formed of indium tin oxide (ITO), NPB is deposited as a host material at a rate of 1 μs / sec and simultaneously a P-type dopant (HAT-CN) represented by Chemical Formula 13 is deposited on the host material 100. Co-evaporation was performed at a ratio of about 5 parts by weight to parts by weight to form a 100 mm thick first layer. The compound according to Example 1 was deposited on the first layer to a thickness of 300 mm 3 to form a second layer. MCBP represented by Chemical Formula 14 and Ir (ppy) ₃ represented by Chemical Formula 15 were co-deposited on the second layer at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 300 GPa, and mCBP was about 50 kV on the light emitting layer. The thickness was deposited to form a barrier layer.

On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture a green light emitting device E-1 including the compound according to Example 1 of the present invention.

Except for manufacturing the second layer using each of the compounds according to Examples 3, 4 and 8 of the present invention, the light emitting device E through the substantially same process as the manufacturing process of the light emitting device E-1 -2, E-3 and E-4 were prepared.

Preparation of Comparative Elements 11 and 12

Comparative element 11 was manufactured through the same process as that of manufacturing light emitting device E-1, except that the second layer was manufactured using the compound according to Comparative Example 10 represented by Chemical Formula b.

Comparative element 12 was manufactured by the same process as that of manufacturing light emitting device E-1, except that the second layer was manufactured using the compound according to Comparative Example 11 represented by Chemical Formula c.

Evaluation of power efficiency and lifespan of light emitting device -5

For each of the light emitting elements E-1 to E-4 and the comparative elements 11 and 12 prepared as described above, the luminance was 500 cd in substantially the same manner as the power efficiency measurement experiment for the light emitting elements A-1 to A-4. The power efficiency was measured based on the value at / m ² .

In addition, the lifetimes of the light emitting elements E-1 to E-4 and the comparative elements 11 and 12 were measured in substantially the same manner as the life evaluation experiments for the light emitting elements A-1 to A-4.

Table 5 shows the results of power efficiency and lifespan of the light emitting elements E-1 to E-4 and the comparative elements 11 and 12, respectively. In Table 5, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 5, T ₇₅ means the time taken for the luminance of the light emitting element to be 75% of the initial luminance when the initial luminance of the light emitting element is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

Table 5

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element E-1	30.0	762
Light emitting element E-2	29.8	728
Light emitting element E-3	28.5	711
Light emitting element E-4	28.7	705
Comparative element 11	9.8	217
Comparative element 12	9.2	209

Referring to Table 5, the power efficiency of each of the light emitting elements E-1 to E-4 is at least about 28.5 lm / W or more, while the power efficiency of the comparative element 11 is only about 9.8 lm / W and the power efficiency of the comparative element 12 It can be seen that is only about 9.2 lm / W. Therefore, it can be seen that the power efficiency of the light emitting devices using the compound according to the present invention is superior to that of the comparative devices 11 and 12.

In addition, it can be seen that the lifespan of each of the light emitting elements E-1 to E-4 is at least about 705 hours or more, whereas the lifespan of the comparative element 11 is only about 217 hours and the lifespan of the comparative element 12 is only about 209 hours. Therefore, it can be seen that the lifespan of the light emitting devices using the compound according to the present invention is longer than that of the comparative devices 11 and 12.

In addition, considering that the life characteristic evaluation of the light emitting device is performed under an acceleration condition (severe condition) of 85 ° C., the life characteristics of the light emitting device including the compound according to the present invention are superior to those of the comparative devices 11 and 12, It can be seen that the light emitting device manufactured using the compound according to the present invention has good heat resistance.

Manufacturing of Light Emitting Diodes F-1 to F-14

On the first electrode formed of indium tin oxide (ITO), the compound according to Example 1 is deposited as a host material at a rate of 1 Å / sec and simultaneously is a P-type dopant represented by Chemical Formula 13 (HAT-CN). Was co-evaporated at a ratio of about 5 parts by weight to 100 parts by weight of the host material to form a first layer having a thickness of 100 mm 3. The compound according to Example 1 was deposited on the first layer to a thickness of 300 mm 3 to form a second layer.

A compound represented by the following Chemical Formula 19 and a compound represented by the following Chemical Formula 20 were co-deposited on the second layer at a weight ratio of 100: 5 to form a light emitting layer having a thickness of about 200 μs.

Thereafter, the compound represented by Chemical Formula 21 and Liq represented by Chemical Formula 18 were co-deposited on a light emitting layer in a 50:50 weight ratio to form an electron transport layer having a thickness of about 360 Pa. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by using Liq represented by Formula 18.

[Formula 19]

[Formula 20]

[Formula 21]

The blue light emitting device F-1 including the compound according to Example 1 of the present invention was prepared by the above method.

Also, except for forming the first layer and the second layer by using the compounds according to Examples 2 to 14, respectively, the host material is substantially the same as the process of manufacturing the light emitting device F-1. Through the light emitting device F-1 to F-14 was produced.

Preparation of Comparative Elements 13-20

Except for forming the first layer and the second layer by using the compound according to Comparative Examples 1 to 8, the host material through the comparative element 13 to substantially the same process as the manufacturing process of the light emitting device F-1 20 was prepared.

Evaluation of Power Efficiency and Lifespan of Light-Emitting Element-6

The light emitting devices F-1 to F-14 and the comparative devices 13 to 20 were each dispensed with a UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere. Each of the and the comparative elements and the cover glass were bonded and cured by irradiation with UV light. For each of the light emitting elements F-1 to F-14 and the comparative elements 13 to 20 prepared as described above, power efficiency was measured based on the value when the luminance was 500 cd / m ² . The results are shown in Table 6.

In addition, the lifetimes of each of the light emitting elements F-1 to F-14 and the comparative elements 13 to 20 were measured using a life meter installed in a measuring oven maintained at a constant temperature of about 85 ° C. The results are shown in Table 6.

In Table 6, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 6, T ₇₅ means the time taken for the luminance of the light emitting element to be 75% of the initial luminance when the initial luminance of the light emitting element is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

Table 6

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element F-1	8.70	145
Light emitting element F-2	7.60	121
Light emitting element F-3	8.50	135
Light emitting element F-4	8.00	130
Light emitting element F-5	7.40	141
Light emitting element F-6	7.10	120
Light emitting element F-7	7.00	115
Light emitting element F-8	8.20	127
Light emitting element F-9	7.10	118
Light emitting element F-10	7.80	122
Light emitting element F-11	6.90	116
Light emitting element F-12	7.30	133
Light emitting element F-13	8.40	147
Light emitting element F-14	7.20	137
Comparative element 13	5.61	77
Comparative element 14	5.90	81
Comparative element 15	5.50	75
Comparative element 16	5.00	69
Comparative element 17	5.20	70
Comparative element 18	4.90	61
Comparative Element 19	5.30	72
Comparative element 20	4.10	52

Referring to Table 6, the power efficiency of the comparison element 13 (position 2 or 7) and the comparison element 20 (position 4 or 5) containing a compound where the substitution position between Cz-Cz is different from the compound according to the present invention It can be seen that it is about 5.61 lm / W and about 4.10 lm / W, respectively, and the lifetimes are 77 hours and 52 hours, respectively. On the contrary, it can be seen that the light emitting devices F-1 to F-14 using the compounds according to the present invention having 3 or 6 substitution positions between Cz and Cz show superior power efficiency and lifetime as compared with the comparative devices 13 and 20. In particular, the light emitting device F-6 using the compound according to Example 6 of the present invention having only a substitution position between Cz and Cz as compared with Comparative Element 13 has an increase in power efficiency by about 27% and a long lifetime by about 56%. It can be seen that. In addition, the light emitting device F-2 using the compound according to Example 2 of the present invention having only a substitution position between Cz and Cz as compared to Comparative Device 20 has an increase in power efficiency by about 85% and a long lifetime by about 133%. It can be seen that.

In addition, it can be seen that the power efficiency of the comparative element 14 (position 3 or 6) including the compound where the position of DBF is substituted with the compound according to the present invention is about 5.90 lm / W, and the lifetime is about 81 hours. On the contrary, it can be seen that the light emitting devices F-7, F-9 and F-11 using the compounds according to the present invention, wherein the substitution position of DBF is 1 or 8, have increased power efficiency by at least 16%. At least 41% longer.

On the other hand, the power efficiencies of Comparative elements 15, 16 and 19 comprising compounds different from the compounds according to the invention in that Cz is not centrally located and substituted in the side chain are about 5.45 lm / W, about 5.01 lm / W and It can be seen that it is about 5.27 lm / W and the lifetime is about 75 hours, about 69 hours and about 72 hours. In contrast, it can be seen that the light emitting devices F-1 to F-14 using the compounds according to the present invention in which Cz is located at the center show superior power efficiency and lifetime as compared to the comparative devices 15, 16 and 19. In particular, in comparison with Comparative Device 15 comprising a compound having a Cz-DBT-DBT-Cz structure, the light emitting device F-2 using the compound according to Example 2 of the present invention having a DBT-Cz-Cz-DBT structure was used. It can be seen that the efficiency is increased by about 39% and the life is extended by about 61%. In addition, the light emitting device F-7 using the compound according to Example 7 having the structure of DBF-Cz-Cz-DBF as compared to the comparison device 16 including the compound having the structure Cz-DBF-DBF-Cz It can be seen that the efficiency is increased by about 40% and the life is extended by about 67%.

Furthermore, the power efficiency of the comparative elements 17 and 18 comprising a compound having a structure different from that of the compound according to the present invention in that Cz is included in three or more structures is about 5.20 lm / W and about 4.90 lm / W, respectively. It can be seen that the lifetime is about 70 hours and about 61 hours. In contrast, it can be seen that the light emitting devices F-1 to F-14 using the compounds according to the present invention having only two Cz exhibit excellent power efficiency and lifetime compared to the comparative devices 17 and 18. Particularly, the light emitting device F-2 using the compound according to Example 2 of the present invention having the DBT-Cz-Cz-DBT structure as compared to the comparative device 18 including the compound having the DBT-Cz-Cz-Cz-DBT structure It can be seen that the power efficiency is increased by about 55% and the lifespan is increased by about 98% compared to the comparison element 18.

Manufacturing of Light Emitting Diodes G-1 to G-14

A first blocking layer having a thickness of about 100 μs is formed on the second blocking layer with the compound according to Example 1, and the compound represented by Formula 19 and the compound represented by Formula 20 are 100: 5 by weight on the first blocking layer. Co-deposited to form a light emitting layer of about 200 kHz thickness. Thereafter, the compound represented by Chemical Formula 21 and Liq represented by Chemical Formula 18 were co-deposited at a weight ratio of 50:50 on the emission layer to form an electron transport layer having a thickness of about 360 Pa. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by using Liq represented by Formula 18.

On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture a blue light emitting device G-1 including the compound according to Example 1 of the present invention.

Except that the first blocking layer is manufactured using each of the compounds according to Examples 2 to 14 of the present invention, the light emitting device G- is substantially the same as the process of manufacturing the light emitting device G-1. 2 to G-14 were prepared.

Preparation of Comparative Elements 21 and 28

Comparative elements 21 to 28 were manufactured through substantially the same process as that of manufacturing light emitting device G-1, except that the first blocking layer was manufactured using the compound according to Comparative Examples 1 to 8.

Evaluation of Power Efficiency and Lifespan of Light-Emitting Element-7

For each of the light emitting elements G-1 to G-14 and the comparative elements 21 to 28 prepared as described above, the luminance was 500 cd in substantially the same manner as the power efficiency measurement experiment for the light emitting elements F-1 to F-14. The power efficiency was measured based on the value at / m ² .

In addition, the lifetimes of each of the light emitting elements G-1 to G-14 and the comparative elements 21 to 28 were measured in the same manner as the life evaluation experiments for the light emitting elements F-1 to F-14.

Table 7 shows the results of power efficiency and lifespan of each of the light emitting devices G-1 to G-14 and the comparative devices 21 to 28. In Table 7, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 7, T ₇₅ represents a time taken for the luminance of the light emitting element to be 75% of the initial luminance when the initial luminance of the light emitting element is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

TABLE 7

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element g-1	7.62	127
Light emitting element g-2	6.64	107
Light emitting element g-3	7.39	120
Light emitting element g-4	7.03	114
Light emitting element g-5	6.70	123
Light emitting element G-6	6.39	105
Light emitting element g-7	6.12	102
Light emitting element g-8	7.19	111
Light emitting element g-9	6.21	104
Light emitting element g-10	6.85	109
Light emitting element g-11	6.10	102
Light emitting element g-12	6.32	117
Light emitting element g-13	7.30	131
Light emitting element G-14	6.50	125
Comparative element 21	4.83	66
Comparative element 22	5.07	69
Comparative element 23	4.69	64
Comparative element 24	4.31	59
Comparative element 25	4.47	60
Comparative element 26	4.21	52
Comparative element 27	4.53	62
Comparative Element 28	3.53	45

Referring to Table 7, the power efficiency of the comparison element 21 (position 2 or 7) and the comparison element 28 (position 4 or 5) containing a compound where the substitution position between Cz-Cz is different from the compound according to the present invention It can be seen that they are about 4.83 lm / W and about 3.53 lm / W, respectively, and their lifetimes are 66 and 45 hours, respectively. On the contrary, it can be seen that the light emitting devices G-1 to G-14 using the compounds according to the present invention having a substitution position between Cz and Cz 3 or 6 exhibit superior power efficiency and lifespan as compared with the comparative devices 21 and 28. In particular, the light emitting device G-6 using the compound according to Example 6 of the present invention having only a substitution position between Cz and Cz as compared with Comparative Element 21 increases power efficiency by about 32% and has a lifespan of about 60%. It can be seen. In addition, the light emitting device G-2 using the compound according to Example 2 of the present invention having only a substitution position between Cz and Cz as compared with Comparative Element 28 increases power efficiency by about 88% and extends lifetime by about 137%. It can be seen that.

In addition, it can be seen that the power efficiency of the comparative element 22 (position 3 or 6) including the compound where the position of the DBF is substituted with the compound according to the present invention is about 5.07 lm / W, and the lifetime is about 69 hours. On the contrary, the light emitting devices G-7, G-9 and G-11 using the compounds according to the present invention, wherein the substitution positions of DBF are 1 or 8, have an increase in power efficiency by about 20% and a lifetime compared to that of the comparative device 22. This is about 48% longer.

On the other hand, the power efficiency of the comparative elements 23, 24 and 27 comprising compounds different from the compounds according to the present invention in that Cz is not centrally located and substituted in the side chain is about 4.69 lm / W, about 4.31 lm / W and about 4.53 lm / W and the lifetimes are about 64 hours, about 59 hours and about 62 hours. In contrast, it can be seen that the light emitting devices G-1 to G-14 using the compounds according to the present invention in which Cz is located at the center show superior power efficiency and lifespan as compared to the comparative devices 23, 24 and 27. In particular, compared to Comparative Device 23 including a compound having a Cz-DBT-DBT-Cz structure, the light emitting device G-2 using the compound according to Example 2 having a DBT-Cz-Cz-DBT structure has a power efficiency. It can be seen that this increases by about 42% and the lifespan is extended by about 67%. In addition, the light emitting device G-7 using the compound according to Example 7 having the structure of DBF-Cz-Cz-DBF compared to the comparative device 24 including the compound having the structure Cz-DBF-DBF-Cz has a power It can be seen that the efficiency is increased by about 42% and the life is extended by about 73%.

Furthermore, the power efficiency of the comparative elements 25 and 26 comprising different compounds from the compounds according to the invention in that Cz is included in at least three structures is about 4.47 m / W and about 4.21 lm / W, respectively, and the lifetime is about It can be seen that 60 hours and about 52 hours. In contrast, it can be seen that the light emitting devices G-1 to G-14 using the compounds according to the present invention having only two Cz have superior power efficiency and lifespan compared to the comparative devices 25 and 26. In particular, compared to Comparative Device 26 having the DBT-Cz-Cz-Cz-DBT structure, the light emitting device G-2 using the compound according to Example 2 having the DBT-Cz-Cz-DBT structure has a high power efficiency. It can be seen that the increase is about 58% and the lifespan is about 105% longer.

Manufacturing of Light Emitting Diodes H-1 to H-14

On the first electrode formed of indium tin oxide (ITO), NPB is deposited as a host material at a rate of 1 μs / sec and simultaneously a P-type dopant (HAT-CN) represented by Chemical Formula 13 is deposited on the host material 100. Co-evaporation was performed at a ratio of about 5 parts by weight to parts by weight to form a 100 mm thick first layer. NPB was deposited to a thickness of 300 Å on the first layer to form a second layer. A first blocking layer having a thickness of about 100 μs is formed on the second blocking layer with the compound according to Example 1, and the compound represented by Formula 19 and the compound represented by Formula 20 are 100: 5 by weight on the first blocking layer. Co-deposited to form a light emitting layer of about 200 kHz thickness.

Thereafter, the compound represented by Chemical Formula 21 and Liq represented by Chemical Formula 18 were co-deposited at a weight ratio of 50:50 on the emission layer to form an electron transport layer having a thickness of about 360 Pa. Subsequently, an electron injection layer having a thickness of about 10 μs was formed on the electron transport layer by using Liq represented by Formula 18.

On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture a blue light emitting device H-1 including the compound according to Example 1 of the present invention.

Except that the first blocking layer is manufactured using each of the compounds according to Examples 2 to 14 of the present invention, the light emitting device H- is substantially the same as the process of manufacturing the light emitting device H-1. 2 to H-14 was prepared.

Preparation of Comparative Elements 29-36

Comparative elements 29 to 36 were manufactured by the same process as that of manufacturing the light emitting device H-1, except that the first blocking layer was manufactured using the compound according to Comparative Examples 1 to 8.

Evaluation of Power Efficiency and Lifespan of Light-Emitting Element-8

For each of the light emitting elements H-1 to H-14 and the comparative elements 29 to 36 prepared as described above, the luminance was 500 cd in substantially the same manner as the power efficiency measurement experiment for the light emitting elements F-1 to F-14. The power efficiency was measured based on the value at / m ² .

In addition, the lifespan of each of the light emitting elements H-1 to H-14 and the comparative elements 29 to 36 was measured in substantially the same manner as the life evaluation experiments for the light emitting elements F-1 to F-14.

Table 8 shows the results of power efficiency and lifespan of the light emitting elements H-1 to H-14 and the comparative elements 29 to 36, respectively. In Table 8, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 8, T ₇₅ means the time taken for the luminance of the light emitting device to be 75% of the initial luminance when the initial luminance of the light emitting device is 1,000 cd / m ² . The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.

Table 8

Element No.	Power Efficiency [lm / W]	Life (T ₇₅ @ 85 ° C [hr])
Light emitting element H-1	7.70	128
Light emitting element H-2	6.50	101
Light emitting element h-3	7.40	114
Light emitting element H-4	7.10	112
Light emitting element H-5	6.80	120
Light emitting element H-6	6.30	98
Light emitting element H-7	6.10	96
Light emitting element H-8	7.10	111
Light emitting element H-9	6.20	99
Light emitting element H-10	6.90	103
Light emitting element H-11	6.00	95
Light emitting element H-12	6.20	113
Light emitting element H-13	7.20	133
Light emitting element H-14	6.40	125
Comparative element 29	4.99	68
Comparative element 30	5.25	72
Comparative element 31	4.85	66
Comparative element 32	4.46	61
Comparative element 33	4.63	63
Comparative element 34	4.36	54
Comparative element 35	4.69	64
Comparative element 36	3.65	47

Referring to Table 8, the power efficiency of the comparison element 29 (position 2 or 7) and the comparison element 36 (position 4 or 5) comprising a compound where the substitution position between Cz-Cz is different from the compound according to the present invention It can be seen that it is about 4.99 lm / W and about 3.65 lm / W, respectively, and the lifetimes are 68 hours and 47 hours, respectively. In contrast, it can be seen that the light emitting devices H-1 to H-14 using the compounds according to the present invention having a substitution position of 3 or 6 between Cz and Cz show superior power efficiency and lifespan as compared with the comparative devices 29 and 36. In particular, the light emitting device H-6 using the compound according to Example 6 of the present invention, in which only the substitution position between Cz and Cz is different compared to that of the comparative device 29, the power efficiency is increased by about 26% and the lifetime is increased by about 44%. It can be seen that. In addition, the light emitting device H-2 using the compound according to Example 2 of the present invention having only a substitution position between Cz and Cz in comparison with the comparison device 36 increases power efficiency by about 78% and has a long service life of about 115%. It can be seen.

In addition, it can be seen that the power efficiency of the comparative element 30 (position 3 or 6) including the compound at which the DBF is substituted is different from the compound according to the present invention is about 5.25 lm / W, and the lifetime is about 72 hours. On the contrary, the light emitting devices H-7, H-9 and H-11 using the compounds according to the present invention, wherein the substitution positions of DBF are 1 or 8, have an increased power efficiency by about 14% compared to the comparative device 30, and have a lifetime. This is about 32% longer.

On the other hand, the power efficiencies of Comparative elements 31, 32 and 35 comprising compounds different from the compounds according to the invention in that Cz is not centrally located and substituted in the side chain are about 4.85 lm / W, about 4.46 lm / W and It can be seen that it is about 4.69 lm / W and the lifetime is about 66 hours, about 61 hours and about 64 hours. On the contrary, it can be seen that the light emitting devices H-1 to H-14 using the compounds according to the present invention having Cz at the center show superior power efficiency and lifetime compared to the comparative devices 31, 32 and 35. In particular, the light emitting device H-2 using the compound according to Example 2 according to the present invention having a DBT-Cz-Cz-DBT structure in comparison with the comparative device 31 including the compound having a Cz-DBT-DBT-Cz structure has a It can be seen that the efficiency is increased by about 34% and the life is extended by about 53%. In addition, the light emitting device H-7 using the compound according to Example 7 having the structure of DBF-Cz-Cz-DBF compared to the comparison device 32 having the structure Cz-DBF-DBF-Cz had a power efficiency of about 37. It can be seen that it increases by% and the lifespan is about 57% longer.

Furthermore, the power efficiency of the comparative elements 33 and 34 comprising compounds different from the compound according to the present invention in that Cz is included in three or more structures is about 4.63 m / W and about 4.36 lm / W, respectively, and the lifetime is about It can be seen that it is 63 hours and about 54 hours. In contrast, it can be seen that the light emitting devices H-1 to H-14 using the compounds according to the present invention having only two Cz exhibit superior power efficiency and lifespan compared to the comparative devices 33 and 34. In particular, the light emitting device H-2 using the compound according to Example 2 of the present invention having the DBT-Cz-Cz-DBT structure as compared to the comparative device 34 including the compound having the DBT-Cz-Cz-Cz-DBT structure It can be seen that the power efficiency is increased by about 49% and the life is extended by about 87%.

As described above, the light emitting device having improved power efficiency, lifetime, and thermal stability may be manufactured using the novel compound according to the present invention.

Claims

Compound represented by the following formula (1):

[Formula 1]

In the above formula

L a and L b each independently represent * -L 1 -L 2 -L 3 -L 4- *,

L 1 , L 2 , L 3, and L 4 each independently represent a single bond, -O-, -S-, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. A cycloalkylene group having

Ar 1 and Ar 2 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, 2 to 20 carbon atoms A heterocycloalkyl group having a bicycloalkyl group having 5 to 20 carbon atoms, the following Chemical Formula 2-1 or the following Chemical Formula 2-2,

[Formula 2-1]

[Formula 2-2]

Het 1 and Het 2 each independently represent the following Chemical Formula 3 or the following Chemical Formula 4,

[Formula 3]

[Formula 4]

Where X represents NW, O, S or Si (R 9 ) (R 10 ),

W is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, carbon atoms A bicycloalkyl group having 5 to 20,

Y represents S or O,

Z represents S,

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or A heteroaryl group having 2 to 20 carbon atoms;

l represents an integer of 0 to 3, m, n and o each independently represent an integer of 0 to 4, any one of p and q represents an integer of 0 to 3, and the other represents an integer of 0 to 4, one of r and s represents an integer of 0 to 3, the other represents an integer of 0 to 4,

Substituents represented by Formula 3 are substituted with a compound of Formula 1 at carbon position 1 or 8,

The substituent represented by the formula (4) is substituted with the compound of the formula (1) at the carbon position 3 or 6,

Among the definitions of the substituents described above for Formulas 1 to 4, the alkyl group, aryl group, heteroaryl group, cycloalkyl group, heterocycloalkyl group and bicycloalkyl group are each independently an alkyl group having 1 to 6 carbon atoms and an alkoxy having 1 to 6 carbon atoms Groups, amine groups unsubstituted or substituted with one or more alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 2 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, It is unsubstituted or substituted with one or more substituents selected from the group consisting of 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 hydroxyl group and a carboxy group.
The method of claim 1,

L a and L b each independently represent * -L 1 -L 2 -L 3 -L 4- *,

L 1 , L 2 , L 3 and L 4 each independently represent a single bond or an arylene group having 6 to 20 carbon atoms,

Ar 1 and Ar 2 each independently represent an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, the following Chemical Formula 2-1 or the following Chemical Formula 2-2,

[Formula 2-1]

[Formula 2-2]

Het 1 and Het 2 each independently represent the following Chemical Formula 3 or the following Chemical Formula 4,

[Formula 3]

[Formula 4]

Where X represents NW, O, S or Si (R 9 ) (R 10 ),

W represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,

Y represents S or O,

Z represents S,

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms. ,

m, n, l, o, p, q, r and s each independently represent an integer of 0 to 2.
The method of claim 1,

L a and L b each independently represent a single bond or an arylene group having 6 to 20 carbon atoms,

Ar 1 and Ar 2 are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; Heteroaryl groups having 2 to 20 carbon atoms which are unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; Formula 2-1 or Formula 2-2,

[Formula 2-1]

[Formula 2-2]

Het 1 and Het 2 each independently represent the following Chemical Formula 3 or the following Chemical Formula 4,

[Formula 3]

[Formula 4]

Where X represents O, S or Si (R 9 ) (R 10 ),

Y represents S or O,

Z represents S,

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms. ,

m, n, l, o, p and q each independently represent 0 or 1.
The method of claim 1,

L a and L b each independently represent a single bond or phenylene,

Ar 1 and Ar 2 are each independently a phenyl group unsubstituted or substituted with a methyl group or a phenyl group; Naphthyl group; Or represented by the formula 2-1,

[Formula 2-1]

Het 1 and Het 2 each independently represent the following Chemical Formula 3 or the following Chemical Formula 4,

[Formula 3]

[Formula 4]

Where X represents O, S or Si (R 9 ) (R 10 ),

Y represents S or O,

Z represents S,

R 5 and R 7 each independently represent a methyl group or a phenyl group,

R 9 and R 10 each independently represent a methyl group,

p and r each independently represent 0 or 1,

l, m, q and s each independently represent 0.
The compound of claim 1, wherein the compound of Formula 1 is represented by the following Formula 5.

[Formula 5]

Where

Ar 1 , Ar 2 , L a , L b , R 5 and p are as defined in claim 1,

Ar 1 and Ar 2 are the same as each other, and L a and L b are the same as each other.
The method of claim 1, wherein the compound of Formula 1 is represented by the following formula (6);

[Formula 6]

Where

Ar 1 , Ar 2 , L a , L b , R 7 and r are as defined in claim 1,

Ar 1 and Ar 2 are the same as each other, and L a and L b are the same as each other.
The compound of claim 1, wherein the compound of Formula 1 is represented by Formula 7;

[Formula 7]

Where

Ar 1 , Ar 2 , L a , L b , R 5 and p are as defined in claim 1,

Ar 1 and Ar 2 are the same as each other, and L a and L b are the same as each other.
A first electrode;

Second electrode;

A light emitting layer disposed between the first electrode and the second electrode; And

A light emitting device comprising a hole transport layer, disposed between the first electrode and the light emitting layer, comprising the compound according to any one of claims 1 to 7.
The light emitting device of claim 8, wherein the hole transport layer further comprises a P-type dopant.
The method of claim 8, wherein the hole transport layer

A first layer comprising the compound and a P-type dopant; And

A light emitting device comprising a second layer comprising the compound.
An electronic device comprising the light emitting device according to claim 8.
The electronic device of claim 11, wherein the electronic device is a display device or a lighting device.