KR101492527B1 - Organic light-emitting diode including aryl substituted antracene derivatives - Google Patents

Abstract

The present invention provides an organic light emitting device comprising a light emitting layer and an electron transporting layer between a first electrode and a second electrode, wherein the electron transporting layer contains one or more anthracene derivatives selected from compounds represented by the following formula (A) Wherein L ₁ , L ₂ , Y, Z, m and m 'are the same as defined in the detailed description of the invention, and the organic luminescent device comprises at least one anthracene derivative selected from compounds represented by the following formula Do.
[Chemical Formula A]

Description

[0001] The present invention relates to an organic light-emitting device including an organic light-emitting diode (OLED) including an aryl-substituted anthracene derivative in an emitting layer and an electron-

The present invention relates to an organic light emitting device including an aryl-substituted anthracene derivative in each of a light emitting layer and an electron transporting layer, and more particularly, to an organic light emitting device capable of lowering a driving voltage, will be.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. In contrast, an organic light emitting diode (OLED), a new flat display device, is a display using an auto-luminescent phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material Should be preceded.

On the other hand, in the organic light emitting device, the charges injected from both electrodes are recombined in the light emitting layer to emit light, and the moving speed of the holes is faster than the electron moving speed, so that the efficiency deterioration due to part of the holes escaping from the light emitting layer . Therefore, there is a demand for an electron transporting material having a high electron mobility, and a light emitting material capable of exhibiting low driving voltage characteristics and high light emitting efficiency in combination with the electron transporting material should be appropriately selected.

In order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent light emitting efficiency and high stability in a thin film state, in Registration No. 10-0691543 (Mar. 3, 2007), an anthracene- Discloses an organic luminescent device using an organic compound having one or two hetero functional groups introduced therein, and JP 10-2012-0104204 (2012.09.20) describes an organic luminescent device using an organic compound to which one or two hetero functional groups are introduced, wherein a pyridoindole derivative is substituted with a substituted anthracene ring structure Discloses an organic light emitting device using a coupled organic compound and also a technique for realizing a high efficiency and a low driving voltage of an organic light emitting device through combination of the electron transporting material and a light emitting material, -0026989 (Mar. 16, 2011) discloses an organic light-emitting device including an anthracene derivative in the light emitting layer and a pyrene derivative in the electron transport layer It can control.

However, in spite of efforts to manufacture an electron transporting material for an organic light emitting device, development of a device having a low driving voltage and a high light emitting property is not enough, And the need for such a system is continuously required.

Patent Registration No. 10-0691543 (Mar. 3, 2007)

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20)

Published Patent Application No. 10-2011-0026989 (March 16, 2011)

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic light emitting device having low-voltage driving characteristics and excellent luminous efficiency through appropriate combination of a material for an electron transporting layer and a material for a light emitting layer.

The present invention provides an organic light emitting device comprising an electron transporting layer and a light emitting layer between a first electrode and a second electrode, wherein the electron transporting layer comprises one or more anthracene derivatives selected from compounds represented by the following formula (A) There is provided an organic light emitting device comprising at least one anthracene derivative selected from compounds represented by the following formula (B).

  (A)

In the above formula (A)

또는

이며,L ₁ is

or

Lt;

Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero ring having 1 to 50 carbon atoms An aryl group, or a substituted or unsubstituted C1 to C30 silyl group; Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI >group; m and m 'are integers of 1 to 8; When the substituents Y and Z are not bonded to the carbon of the aromatic ring of the naphthyl group or the anthracenyl group, hydrogen is bonded;

Wherein X ₁ to X ₅ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroatom having O, N or S And any one selected from a heteroaryl group, a cyano group, a nitro group, a halogen group of a small number of 2 to 50,

Wherein X ₁ , At least one of X ₂ , X ₄ , and X ₅ is a heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom; And X ₆ is a heteroaryl group having 2 to 20 carbon atoms containing a nitrogen atom.

[Chemical Formula B]

In the above formula (B)

Y, Z, m and m 'are the same as defined in the above formula (A)

또는

이며,L ₂ is

or

Lt;

Each of Q ₁ to Q ₅ independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a cyano group, a nitro group, a halogen group , ≪ / RTI >

인 경우에 상기 화학식 A로 표시되는 화합물에서의 상기 치환기 L₁ 은

이되, 상기 화학식 B로 표시되는 화합물에서의 상기 치환기 Q_1, Q₂, Q₄ 및 Q₅ 중 적어도 하나는 탄소수 6 내지 20의 아릴기로서, 상기 탄소수 6 내지 20의 아릴기의 개수 및 이의 페닐기에 결합되는 위치는 상기 화학식 A에서의 L₁ 의 페닐기에 결합되는 치환기인 질소원자를 포함 하는 탄소수 2 내지 20의 헤테로아릴기의 개수 및 상기 헤테로아릴기가 결합되는 페닐기내의 방향족 탄소자리의 위치와 동일하도록 상기 화학식 B의 페닐기에 상기 탄소수 6 내지 20의 아릴기가 결합될 수 있다. Wherein Q ₆ is an aryl group having a carbon number of 6 to 20 carbon atoms,
When the substituent L ₂ in the compound represented by the above formula (B) is Q ₆ , The substituent L ₁ in the compound represented by the above formula (A) is X ₆ ,
When the substituent L ₂ in the compound represented by the formula (B) is

, The substituent L < ₁ > in the compound represented by the above formula (A)

At least one of the substituents Q _1, Q ₂ , Q ₄ and Q ₅ in the compound represented by the formula (B) is an aryl group having 6 to 20 carbon atoms, and the number of the aryl groups having 6 to 20 carbon atoms and the phenyl group where the bond at a position same as that of the aromatic carbon position in the phenyl group count and group the heteroaryl coupling having 2 to 20 hetero aryl groups containing a substituent of a nitrogen atom that is bonded to the phenyl group of L ₁ in the general formula a The aryl group having 6 to 20 carbon atoms may be bonded to the phenyl group of the formula (B).

The organic electroluminescent device according to the present invention has characteristics of low voltage driving and excellent luminous efficiency as compared with application of existing materials to an electron transporting layer and a light emitting layer, thus providing a stable and excellent device.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

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

The present invention provides an organic light emitting device comprising a light emitting layer and an electron transporting layer between a first electrode and a second electrode, wherein the electron transporting layer includes an anthracene derivative substituted with an aryl group containing a heteroaryl group, And an anthracene derivative having a molecular structure similar to that of an anthracene derivative.

More specifically, the present invention relates to an organic light emitting device comprising an electron transporting layer and a light emitting layer between a first electrode and a second electrode, wherein the electron transporting layer contains one or more anthracene derivatives selected from compounds represented by the following formula (A) And at least one anthracene derivative selected from compounds represented by the following formula (B) is contained in the light emitting layer.

 (A)

In the above formula (A)

또는

이며,L ₁ is

or

Lt;

Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero ring having 1 to 50 carbon atoms An aryl group, or a substituted or unsubstituted C1 to C30 silyl group; Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI >group; m and m 'are integers of 1 to 8; When the substituents Y and Z are not bonded to the carbon of the aromatic ring of the naphthyl group or the anthracenyl group, hydrogen may be bonded thereto;

Wherein X ₁ to X ₅ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroatom having O, N or S And any one selected from a heteroaryl group, a cyano group, a nitro group, a halogen group of a small number of 2 to 50,

At least one of X ₁ , X ₂ , X ₄ and X ₅ is a heteroaryl group having 2 to 20 carbon atoms containing a nitrogen atom and X ₆ is a heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom .

[Chemical Formula B]

In the above formula (B)

Y, Z, m and m 'are the same as defined in the above formula (A)

또는

이며,L ₂ is

or

Lt;

인 경우에 상기 화학식 A로 표시되는 화합물에서의 상기 치환기 L₁ 은

이되, 상기 화학식 B로 표시되는 화합물에서의 상기 치환기 Q_1, Q₂, Q₄ 및 Q₅ 중 적어도 하나는 탄소수 6 내지 20의 아릴기로서, 상기 탄소수 6 내지 20의 아릴기의 개수 및 이의 페닐기에 결합되는 위치는 상기 화학식 A에서의 L₁ 의 페닐기에 결합되는 치환기인 질소원자를 포함 하는 탄소수 2 내지 20의 헤테로아릴기의 개수 및 상기 헤테로아릴기가 결합되는 페닐기내의 방향족 탄소자리의 위치와 동일하도록 상기 화학식 B의 페닐기에 상기 탄소수 6 내지 20의 아릴기가 결합될 수 있다. Each of Q ₁ to Q ₅ is the same or different from each other and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, a cyano group, group, and any one is selected from a halogen group, wherein Q ₆ may be aryl having 6 to 20 carbon atoms in the date.
When the substituent L ₂ in the compound represented by the formula (B) is Q ₆ , the substituent L ₁ in the compound represented by the formula (A) is X ₆ ,
When the substituent L ₂ in the compound represented by the formula (B) is

, The substituent L < ₁ > in the compound represented by the above formula (A)

At least one of the substituents Q _1, Q ₂ , Q ₄ and Q ₅ in the compound represented by the formula (B) is an aryl group having 6 to 20 carbon atoms, and the number of the aryl groups having 6 to 20 carbon atoms and the phenyl group where the bond at a position same as that of the aromatic carbon position in the phenyl group count and group the heteroaryl coupling having 2 to 20 hetero aryl groups containing a substituent of a nitrogen atom that is bonded to the phenyl group of L ₁ in the general formula a The aryl group having 6 to 20 carbon atoms may be bonded to the phenyl group of the formula (B).

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms.

The aryl group used in the compound of the present invention means an aromatic system composed of a hydrocarbon containing at least one ring. When the substituent is present, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like. At least one hydrogen atom of the aryl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, , An amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group" An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms , A heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 2 to 24 carbon atoms in which the remaining ring atoms contain 1 to 5 hetero atoms selected from N, O, P or S, Can be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. May be substituted with the same substituents as those in the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

In consideration of the range of the alkyl or aryl group in the above "substituted or unsubstituted C1-C30 alkyl group" or "substituted or unsubstituted C6-C50 aryl group", it is preferable that the number of carbon atoms is 1 to 30 And the number of carbon atoms of the alkyl group of 6 to 50 carbon atoms and the number of carbon atoms of the aryl group of 6 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when the substituent is considered to be unsubstituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

On the other hand, in the present invention, the phrase "(organic layer) contains at least one organic compound" means that one or more organic compounds belonging to the category of the present invention (organic layer) Compound "as used herein.

In the present invention, at least one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the compound represented by the formula (A) used in the electron transport layer is a heteroaryl having 2 to 20 carbon atoms , The heteroaryl group may be any one substituent selected from the group consisting of the structural formulas 1 to 6. [

 [Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

 [Structural Formula 6]

In the formulas 1 to 6, T ₁ to T ₈ are the same or different and independently of one another are C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ) S; R ₁ to R ₁₃ are the same or different from each other and independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, and each of R ₁ to R 6 in each of the structural formulas 1 to 6, And one of R < ₁₃ > may be a single bond forming a bond with the phenyl group of the substituent L < ₁ > in the above formula (A).

Here, the formula 3 may include a compound represented by the formula 3-1 by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

Provided that T ₁ to T ₅ and R ₃ and R ₄ are the same as defined above.

In the present invention, when at least one of the substituents X ₁ to X ₅ in the formula (A) is a heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom, the heteroaryl group may have a plurality of rings. When the heteroaryl group has a plurality of rings, it is considered that all the rings are composed of heteroaryl containing nitrogen, or a ring of a heteroaryl moiety containing nitrogen and a ring of aryl moieties not containing a heteroatom Can be. In this case, the moiety bonded to the phenyl group of the substituent L ₁ of the above formula (A) may be a ring moiety including nitrogen, or may be a ring of an aryl moiety not containing nitrogen.

If T ₁ to T ₃ have at least one nitrogen atom and T ₄ , T ₅ , R ₃ and R ₄ are an aryl group moiety not containing nitrogen in the case of the structural formula 3, The moiety bonded to the phenyl group of the substituent A ₁ in the A may be any one of T ₁ to T ₃ , or any one selected from T ₄ , T ₅ , R _3, and R ₄ may be bonded to the phenyl group have.

In this case, preferably, the ring of the aryl group moiety not containing nitrogen may be a moiety bonded to the phenyl group of the substituent L ₁ of the above formula (A).

This can be similarly understood in the above-mentioned [Structural formulas 4] to [Structural formula 6].

In the present invention, Y and Z in formula (A) are the same or different and independently of each other, hydrogen, deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; , And m and m 'may each be an integer of 1 to 4.

In this case, in the present invention, only one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the above formula (A) may be any substituent selected from the above-mentioned structural formulas 1 to 6.

In the present invention, each of the substituents in the structural formulas 1 to 6 may be substituted with 1 to 3 nitrogen atoms in the aromatic carbon residue in the substituent to form a heteroaryl group.

When the nitrogen atom is contained in the aromatic carbon site, the nitrogen atom can make the aromatic ring system in a state lacking electrons and can serve as an electron transport layer.

In the present invention, X ₆ in the substituent L ₁ of the above-mentioned formula (A) may be any one substituent selected from the structural formulas 1 to 6.

In the present invention, at least one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the above-mentioned formula (A) may be any one of substituents 101 to 606 shown below.

[Substituent 101] [Substituent 102] [Substituent 103]

[Substituent group 104] [Substituent group 105] [Substituent group 106]

[Substituent group 107] [Substituent group 108] [Substituent group 109]

[Substituent group 110] [Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent 207] [Substituent 208]

[Substituent group 301] [Substituent group 302] [Substituent group 303]

[Substituent group 304] [Substituent group 305] [Substituent group 306]

[Substituent group 307] [Substituent group 308]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent group 404] [Substituent group 405] [Substituent group 406]

[Substituent group 407] [Substituent group 408] [Substituent group 409]

[Substituent group 410] [Substituent group 411] [Substituent group 412] [Substituent group 413]

[Substituent group 501] [Substituent group 502] [Substituent group 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, A substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each of May be fused to adjacent groups to form a ring,

n is an integer of 0 to 9, and when the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of the substituents 101 to 606, hydrogen is bonded, and one of the Rs is a substituent Lt; ₁ >

In this case, in the present invention, only one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the above-mentioned formula (A) may be any substituent selected from the substituents 101 to 606.

In the organic luminescent device of the present invention, the portion excluding the substituent L ₁ in the compound represented by the formula (A) used in the electron transport layer and the portion excluding the substituent L ₂ in the compound represented by the formula (B) The compound represented by the formula (A) and the compound represented by the formula (B) in the organic light emitting device are characterized in that only the substituents L ₁ and L ₂ bonded to the anthracenyl group are different from each other. That is, in the organic light emitting device of the present invention, the portion excluding the substituent L ₁ in the compound represented by the formula (A) and the portion excluding the substituent L ₂ in the compound represented by the formula (B) used in the light emitting layer are the same, And the substituent substituted for the anthracenyl group and the naphthyl group has the same substituent group. Thus, the substituent group L < ₁ > in the compound represented by the formula (A) used in the electron transport layer And the substituent L ₂ in the compound represented by the formula (B) used in the light emitting layer have the same common backbone. For example, in the compound represented by the formula (A) used in the electron transport layer in the organic light emitting device of the present invention, the part excluding the substituent L ₁ and the part excluding the substituent L ₂ in the compound represented by the formula (B) A structure in which the 5-position of the naphthyl group is substituted with methyl and the anthracenyl group is substituted with only hydrogen without substituent can be used, and as another example, the substituent L < ₁ > in the compound represented by the formula A used in the electron- And the substituent L ₂ in the compound represented by the formula (B) used in the light emitting layer are respectively a structure in which the 4-position of the naphthyl group is phenyl and a 5-position methyl is substituted in the anthracenyl group .

In the present invention, the substituent Q ₁ in the compound represented by the general formula (B) To Q ₅ is an aryl group having 6 to 20 carbon atoms, wherein the number of the aryl groups having 6 to 20 carbon atoms and the position bonded to the phenyl group includes a nitrogen atom which is a substituent bonded to the phenyl group in the formula (A) The aryl group having 6 to 20 carbon atoms is bonded to the phenyl group of the formula (B) such that the number of the heteroaryl group having 2 to 20 carbon atoms and the aromatic carbon position in the phenyl group to which the heteroaryl group is bonded are bonded.

That is, when X ₃ and X ₄ are a heteroaryl group having 2 to 20 carbon atoms in the phenyl group of the substituent L ₁ of the anthracene derivative represented by the formula (A) used in the electron transport layer and hydrogen is bonded in the remaining cases, Q ₃ and Q ₄ bonded to the phenyl group of the substituent L ₂ in the compound represented by the formula (B) are also bonded to the aryl group having 6 to 20 carbon atoms corresponding thereto. As another example, if X ₄ in the phenyl group of the substituent L ₁ of the anthracene derivative represented by the formula (A) used in the electron transport layer is a heteroaryl group having 2 to 20 carbon atoms and the remainder is hydrogen, Q ₄ bonded to the phenyl group of the substituent L ₂ in the compound represented by the formula (B) used also corresponds to the aryl group having 6 to 20 carbon atoms, and the substituents substituted on the phenyl group in the substituents L ₁ and L ₂ are represented by the formulas The compound of formula (B) has a similar structure to each other.

More preferably, in the present invention, only one of the substituents Q ₁ , Q ₂ , Q ₄ and Q ₅ in the compound represented by the formula (B) used in the light emitting layer is an aryl group having 6 to 20 carbon atoms, Only _one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the formula (A) used is a heteroaryl group having 2 to 20 carbon atoms, and the position at which the aryl group having 6 to 20 carbon atoms is bonded to the phenyl group, May be bonded such that the heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom is the same as the position of the aromatic carbon position of the phenyl group to which the heteroaryl group is bonded.

The organic light emitting device of the present invention may further include at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, and an electron injecting layer.

In the present invention, the light emitting layer is composed of a host and a dopant, and the compound represented by the formula (B) in the present invention can be used as a host material.

The organic light emitting device according to the present invention may include the compound represented by the above formula (A) and the compound represented by the formula (B) in various laminated structures interposed between the first electrode and the second electrode (anode and cathode) , The compound represented by the formula (A) is used for the electron transport layer, and the compound represented by the formula (B) is used as the host light emitting material in the light emitting layer, thereby optimizing the light emitting property and power efficiency of the organic light emitting device. When the compound having the structure of the formula (A) is used as the material for the electron transport layer and the compound having the structure (B) is used as the host material of the luminescent layer, the compounds of the above structure have a similar skeleton, It is presumed that the low-voltage driving characteristics and the light-emitting efficiency are improved by arranging the molecules arranged in the three-dimensional space or the arrangement form of the molecules in the different layers located in different layers.

Specific examples of the dopant material used in the light emitting layer in the present invention include pyrene-based compounds, deuterated-substituted pyrene-based compounds, fluorene-based compounds, deuterium-substituted fluorene-based compounds, benzofluorene-based compounds, A dibenzofluorene-based compound, a dibenzofluorene-based compound, a dibenzofluorene-based compound, a dibenzofluorene-based compound, an indenophenanthrene-based compound, a deuterium-substituted indenophenanthrene-based compound, an arylamine, an arylamine substituted with deuterium, Substituted styryl compounds, styryl substituted styryl compounds, substituted peryl-based compounds, pyrrole-based compounds, deutero-substituted pyrrole-based compounds, hydrazone based compounds, deuterated substituted hydrazone based compounds, carbazole based compounds, deuterated substituted carbazole based compounds, Starburst-based compounds, deuterium-substituted starburst-based compounds, oxadiazole-based compounds, deuterium A substituted oxadiazole-based compound, coumarine, deuterium-substituted coumarine, and the like, but the present invention is not limited thereto.

Further, in the light emitting layer, a host other than the host compound represented by the formula (B) of the present invention may be used. As the host used in this case, there may be used Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) 2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazole- benzene), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP Deuterium substituents, and the like, but the present invention is not limited thereto.

  PVK ADN

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

Meanwhile, in the present invention, the electron transporting layer may be used by mixing a compound represented by the general formula (A) and a compound for the electron transport different from the compound represented by the general formula (A). That is, the electron transporting layer may contain other kinds of electron transporting compounds in addition to the anthracene derivative represented by the formula (A) of the present invention.

Here, the electron transport layer compound different from the anthracene derivative is an anthracene derivative having the structure of the formula (A), but may be a compound of a different kind or may be an anthracene derivative having no structure of the formula (A) A nonanthracene-based compound having no structure represented by the formula (A) can be used as another electron transport layer compound.

As the electron transport layer compound having no structure of the above formula (A), oxadiazole derivatives PBD, BMD, BND, or compounds having the structure of the following formula (C) can be used. To Examples of the compound having the structure of Formula C, Liq, Alq ₃ Etc. may be used.

≪ RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond; Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

M is 1 to 3 when M is boron or aluminum, and n is any of 0 to 2 and satisfies m + n = 3.

In the present invention, Y may be the same or different and independently of each other may be any one selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring. Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term " substituted aryl group "

When the compound represented by the formula (A) in the present invention is mixed with an electron transporting compound which is different from the compound represented by the formula (A) and used in an electron transporting layer, the mixing ratio thereof is 10:90 to 90:10 , And preferably from 25:75 to 75:25.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ], Etc. However, the present invention is not limited thereto.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device.

As the material for the electron transport layer, PBD, BMD, BND, the compound represented by the above-described formula (C), etc. may be used in addition to the compound of the formula (A) used in the present invention.

On the other hand, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

The organic light emitting layer may comprise a host and a dopant.

According to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

At this time, the dopant used in the light emitting layer may be a compound represented by the following formula (1) or (2).

[Chemical Formula 1] < EMI ID =

In the above formulas (1) and (2)

A is an aromatic ring group having no hetero atom, which is a substituted or unsubstituted aromatic ring group having 6 to 50 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, provided that when n is 2 or more, each of the amine groups bonded to A is the same Can be different.

When A is an aromatic ring group having no heteroatom, A may preferably be a compound represented by the following formulas (A1) to (A10).

[Chemical Formula A1] [Chemical Formula A2] [Chemical Formula A3] Chemical Formula A4 [Chemical Formula A5]

(A9) a compound of the formula (A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with the adjacent groups.

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other, and Y ₁ And Y ₂ each independently represents a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, A substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted C6 to C24 A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. And Y ₁ to Y ₂ are the same or different from each other and can form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form , And the substituted hydrogen may be substituted with deuterium or alkyl, respectively, and may be the same or different from each other.

The B Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer from 1 to 4.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 4]

[Substituent group 5] [Substituent group 6] [Substituent group 7] [Substituent group 8]

[Substituent group 9] [Substituent group 10] [Substituent group 11] [Substituent group 12]

[Substituent group 13] [Substituent group 14] [Substituent group 15] [Substituent group 16]

[Substituent group 17] [Substituent group 18] [Substituent group 19] [Substituent group 20]

[Substituent group 21] [Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent 25] [Substituent 26]

[Substituent group 27] [Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33] [Substituent group 34]

[Substituent group 35] [Substituent group 36] [Substituent group 37] [Substituent group 38]

[Substituent group 39] [Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45] [Substituent group 46]

[Substituent group 47] [Substituent group 48] [Substituent group 49] [Substituent group 50]

[Substituent group 51] [Substituent group 52]

In the above substituents, R may be the same or different and independently of one another selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylthio having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a di (substituted or unsubstituted C1-C60 alkyl) amino group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, , Each of which may be substituted from 1 to 12, and each substituent may form a condensed ring with adjacent groups.

The light emitting layer may further include various hosts and various dopant materials in addition to the dopant.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

<Examples>

Synthesis Example 1. Synthesis of [Compound 1]

Synthesis Example 1-1 Synthesis of (10- (naphthalen-2-yl) anthracene-9-yl) boronic acid

Synthesis Example 1-1-a) Synthesis of 9- (naphthalen-2-yl) anthracene

2-naphthalene boronic acid 27.2g (158mmol), 9- bromo-anthracene 34g (132mmol), potassium carbonate 36.6g (264mmol), Pd (PPh 3) 4 3g (2mmol) in a round bottom flask, 70ml of water, 180ml of toluene and 180 ml of tetrahydrofuran was added and the mixture was subjected to a reflux reaction.

After completion of the reaction, the layers were separated to remove the aqueous layer, and the organic layer was concentrated under reduced pressure to obtain 27 g (yield: 81%) of 9- (naphthalene-2-yl) anthracene by column chromatography.

Synthesis Example 1-1-b) Synthesis of 9-bromo-10- (naphthalen-2-yl) anthracene

27 g (0.108 mol) of 9- (naphthalen-2-yl) anthracene prepared in Synthesis Example 1-1-a) and 250 ml of dichloromethane were placed in a round bottom flask, and the crystals were dissolved at room temperature. , And 17.2 g (0.107 mol) of bromine were diluted in 50 ml of dichloromethane and reacted slowly. After the completion of the reaction, the water layer was removed and the organic layer was concentrated under reduced pressure, and crystals were precipitated from methanol and then recrystallized to obtain 26.4 g of yellow 9-bromo-10- (naphthalen- ) Was obtained

Synthesis Example 1-1-c) Synthesis of (10- (naphthalen-2-yl) anthracene-9-yl) boronic acid

9-bromo-10- (naphthalen-2-yl) anthracene (26 g, 68 mmol) prepared in Synthesis Example 1-1-b was dissolved in 210 mL of THF in a round bottom flask. N-Butyllithium (51 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (33.1 g, 95 mmol) was added at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N aqueous hydrochloric acid solution was added to adjust the acidity. The solution was extracted with EA, and the solvent was removed to obtain crystals (hexane: 10 - (naphthalene-2-yl) anthracene-9-yl) boronic acid 15g (yield: 73%).

Synthesis Example 1-2) Synthesis of 1- (4-bromophenyl) -1H-1,2,4-triazole

To a round bottom flask was added 37.3 g (132 mmol) of 1-bromo-4-iodobenzene, 14.2 g (125 mmol) of (1H-1,2,4- triazol- 1 -yl) boronic acid, 36.6 g ), ₃ g (2 mmol) of Pd (PPh3) ₄ , 70 ml of water, 180 ml of toluene and 180 ml of tetrahydrofuran were placed and refluxed.

After completion of the reaction, the layers were separated to remove the aqueous layer, and the organic layer was concentrated under reduced pressure to obtain 22 g (yield: 75%) of 1- (4-bromophenyl) -1H- &Lt; / RTI &gt;

Synthesis Example 1-3) Synthesis of [Compound 1]

1- (4-bromophenyl) -1H-1,2,4-triazole prepared in Synthesis Example 1-2, instead of 9-bromoanthracene used in Synthesis Example 1-1-a, [Compound 1] was synthesized by the same method except that 10- (naphthalen-2-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1 was used instead of naphthaleneboronic acid. (4.0 g, yield 49%).

MS (MALDI-TOF): m / z 447 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

132.6,126.1,126.2,127.7,127.9,128.1,128.2,130.1,130.9,132.7,133.1,133.6,134.2,134.7,137.2,143.3,153.6 [32C]

Synthesis Example 2. Synthesis of [Compound 2]

Synthesis Example 2-1) Synthesis of 6- (3-bromophenyl) quinoxaline

Bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene used in Synthesis Example 1-2, (1H-1,2,4-triazol- 6- (3-bromophenyl) quinoxaline was obtained (22 g, yield 75%), except that 6-quinoxaline boronic acid was used instead of boronic acid.

Synthesis Example 2-2) Synthesis of [Compound 2]

(3-bromophenyl) quinoxaline prepared in Synthesis Example 2-1 instead of 1- (4-bromophenyl) -1H-1,2,4-triazole used in Synthesis Example 1-3 Was used to synthesize [Compound 2]. (3.4 g, yield 46%).

MS (MALDI-TOF): m / z 509 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.3, 125.6, 126.1, 126.2, 126.8, 127.1, 127.7, 127.9,128.1,128.2,129.7,130.9,132.7,133.1,134.2,137,137.2,140.8,141.1,142.7,144.8 [

Synthesis Example 3. Synthesis of [Compound 3]

Synthesis Example 3-1) Synthesis of 2- (4-bromophenyl) pyrimidine

Except that 2-pyrimidylboronic acid was used in place of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2, Bromophenyl) pyrimidine (20 g, yield 76%).

Synthesis Example 3-2) Synthesis of [Compound 3]

(4-bromophenyl) pyrimidine prepared in Synthesis Example 3-1 instead of 1- (4-bromophenyl) -1H-1,2,4-triazole used in Synthesis Example 1-3 [Compound 3] was synthesized using the same method except that (3.7 g, yield 47%).

MS (MALDI-TOF): m / z 459 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

117.7,125.6,126.1,126.2,127.2,127.7,128,128.1,128.2,130.9,132.7,133.1,133.6,134.2,137.2,156.1,164.2 [34C]

Synthesis Example 4. Synthesis of [Compound 4]

Synthesis Example 4-1) Synthesis of 2- (4-bromophenyl) -1,8-naphthyridine

Except that (1,8-naphthyridin-2-yl) boronic acid was used in place of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2 Was used to obtain 2- (4-bromophenyl) -1,8-naphthyridine (21 g, yield 77%).

Synthesis Example 4-2) Synthesis of [Compound 4]

(4-bromophenyl) -1H-1,2,4-triazole prepared in Synthesis Example 4-1 was used instead of 1- (4-bromophenyl) -1H- , 8-naphthyridine was used to synthesize [Compound 4]. (3.1 g, yield 49%)

MS (MALDI-TOF): m / z 509 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

128.1, 128.2, 130.9, 132.2, 132.7, 133.1, 134.2, 135.2, 137.2, 137.9, 138.4, 153, 154.6, 156.2 [38C]

Synthesis Example 5. Synthesis of [Compound 5]

Synthesis Example 5-1) Synthesis of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid

Scheme 5-1)

5-Bromo-2-methyl-2H-1,2,3-benzotriazole (8.5 g, 40 mmol) was dissolved in 650 mL of THF in a round bottom flask. The n-BuLi (30 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (5.9 g, 56 mmol) was added thereto at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N HCl was added to adjust the acidity. The product was extracted with EA, and the solvent was removed to obtain crystals with hexane to obtain the product. (5.5 g, yield 78%)

Synthesis Example 5-2) Synthesis of 5- (3-bromophenyl) -2-methyl-2H-benzo [d] [1,2,3] triazole

Instead of the 6-quinoxaline boronic acid used in Synthesis Example 2-1), 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid prepared in Synthesis Example 5-1) Methyl-2H-benzo [d] [1,2,3] triazole (21 g, yield 70%) was obtained by using the same method except for using 2-

Synthesis Example 5-3) Synthesis of [Compound 5]

2-methyl-2H-benzo [d] thiazole obtained in Synthesis Example 5-2 instead of 6- (3-bromophenyl) quinoxaline used in Synthesis Example 2-2, [Compound 5] was synthesized by the same method except that [1,2,3] triazole was used. (4.6 g, yield 51%).

MS (MALDI-TOF): m / z 512 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

143.9,125.6,126.1,126.2,126.8,127.4,127.7,127.9,128.1,128.2,129.7,130.1,130.9,132.7,133.1,134.2,136.5,137,137.2,144.3,145.5 [37C]

Synthesis Example 6. Synthesis of [Compound 6]

Synthesis Example 6-1. Synthesis of 2,6-dialkyl substituted 10- (naphthalen-2-yl) anthracene-9-yl boronic acid

Synthesis Example 6-1-a) Synthesis of 2,6-dialkyl-substituted anthracene derivative

2-Methyl-2-hexanol (35 g, 300 mmol) and anthracene (18.4 g, 100 mmol) were added to 50 mL trifluoroacetic acid and refluxed under nitrogen for 24 h. Upon completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The organic layer is concentrated under reduced pressure, and the resulting solid is filtered off and separated by column chromatography. The product was recrystallized from methanol. (6 g, yield 16%).

Synthesis Example 6-1-b) Synthesis of 2,6-dialkyl-substituted 9,10-dibromoanthracene

The 2,6-dialkyl-substituted anthracene (6 g, 16 mmol) synthesized in Synthesis Example 6-1-a was placed in 100 mL of dichloroethane, and bromine (2.1 mL, 40 mmol) was added dropwise with stirring at room temperature for 4 hours. This was poured into water and sodium sulfate was added to consume the residual bromine. This was then extracted with dichloromethane and the organic layer was dried over magnesium sulfate. The resulting material was passed through an alumina column using dichloromethane eluent, then evaporated, and methanol was added to precipitate a pale yellow solid to give about 7.2 g of product.

Synthesis Example 6-1-c) Synthesis of 2,6-dialkyl-substituted 9-bromo-10-naphthalen-2-ylanthracene

7.2 g (13 mmol) of the 2,6-dialkyl-substituted 9,10-dibromoanthracene prepared in Synthesis Example 6-1-b, 2.4 g (13 mmol) of 2-naphthalene boronic acid and 3.7 g g (27 mmol) of Pd (PPh3) _4, 0.3 g ( ₃ mmol) of Pd (PPh3), 15 ml of water, 40 ml of toluene and 40 ml of tetrahydrofuran.

After completion of the reaction, the layers were separated to remove the aqueous layer, and the organic layer was concentrated under reduced pressure, and recrystallized with toluene hexane to obtain a product. (5.0 g, yield 75%).

Synthesis Example 6-1-d) Synthesis of 2,6-dialkyl-substituted 10- (naphthalen-2-yl) anthracene-9-yl boronic acid

The same procedure as in Synthesis Example 1-1-c was repeated except that 2,6-dialkyl-substituted 9-bromo-10- (naphthalen-2-yl) anthracene prepared in Synthesis Example 6-1- -10-naphthalen-2-ylanthracene was used as a starting material.

Synthesis Example 6-2) Synthesis of 5- (3-bromophenyl) -1,10-phenanthroline

The title compound was obtained from 5- (3-bromo-4-methoxyphenyl) -lH-pyrrolo [2,3-d] pyrimidin-4- Phenyl) -1,10-phenanthroline (18 g, yield 67%).

Synthesis Example 6-3) Synthesis of [Compound 6]

Except that 5- (3-bromophenyl) -1,10-phenanthroline prepared in Synthesis Example 6-2 was used instead of 6- (3-bromophenyl) quinoxaline used in Synthesis Example 2-2 Dialkyl-substituted 10- (naphthalen-2-yl) anthracene-9-ylboronic acid prepared in Synthesis Example 6-1 instead of (10-naphthalen- [Compound 6] was synthesized by the same method except that an acid was used. (4.1 g, 48% yield)

MS (MALDI-TOF): m / z 755 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

136.1, 135.7, 136.4, 136.6, 137, 147.3, 149.9, 154.6 [56C]

SYNTHESIS EXAMPLE 7 Synthesis of [Compound 7]

Synthesis Example 7-1) Synthesis of 5-bromo-1,2-diphenyl-1H-benzimidazole

4-Methylbenzenesulfonic acid (3.1 g, 16 mmol) was added to a solution of N ¹ -benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol), 500 mL of dichloromethane and 30 mL of trimethyl orthobenzoate And reacted under nitrogen at room temperature for about 40 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, washed with 40% methanol / water and sodium hydrogencarbonate / water and dried to obtain the product (22.3 g, yield 40%).

Synthesis Example 7-2 Synthesis of (1,2-diphenyl-1H-benzo [d] imidazol-5-yl)

Bromo-10- (naphthalen- 2 -yl) anthracene used in Synthesis Example 1-1-c) -Benzimidazole (7 g, yield 35%). &Lt; RTI ID = 0.0 &gt;

Synthesis Example 7-3) Synthesis of 5- (4-bromophenyl) -1,2-diphenyl-1H-benzo [d] imidazole

(1,2-diphenyl-1H-benzo [b] thiophene-2-carbaldehyde prepared in the above Synthesis Example 7-2) instead of (1H-1,2,4- d] imidazol-5-yl) boronic acid was used as the starting material. (6.5 g, 80% yield)

Synthesis Example 7-4) Synthesis of [Compound 7]

(4-bromophenyl) -1H-1,2,4-triazole prepared in the above Synthesis Example 7-3) instead of 1- (4-bromophenyl) [Compound 7] was synthesized (3.2 g, yield 47%), except that 1,2-diphenyl-1H-benzo [d] imidazole was used.

MS (MALDI-TOF): m / z 649 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

123.6, 149.4 [49C]

Synthesis Example 8 Synthesis of [Compound 8]

Synthesis Example 8-1) Synthesis of 2- (3,5-dibromophenyl) -1,3,4-oxadiazole

Scheme 8-1)

Dibromo-5-iodobenzene was used instead of 1-bromo-4-iodobenzene used in Synthesis Example 1-2), (1H-1,2,4-triazole- (31.3 g, yield 71%) was obtained using the same procedure except that (1,3,4-oxadiazol-2-yl) boronic acid was used instead of 3-

Synthesis Example 8-2) Synthesis of 2- (5-bromo- [1,1'-biphenyl] -3-yl) -1,3,4-oxadiazole

Scheme 8-2)

(3,5-dibromophenyl) -1,3,4-oxadiazole prepared in Synthesis Example 8-1) instead of 1-bromo-4-iodobenzene used in Synthesis Example 8-1) The product was obtained using the same method except that the sol was used and phenylboronic acid was used instead of (1,3,4-oxadiazol-2-yl) boronic acid (25 g, yield 72%).

Synthesis Example 8-3) Synthesis of [Compound 8]

(5-bromo- [l, 4] benzodiazepin-2-one) prepared in the above Synthesis Example 8-2) was used instead of 1- (4-bromophenyl) Biphenyl] -3-yl) -1,3,4-oxadiazole was used to synthesize [Compound 8]. (3.2 g, 44% yield)

MS (MALDI-TOF): m / z 525 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

127.7, 125.6, 126.1, 126.2, 127.1, 127.6, 127.7, 127.9, 128.1, 128.2, 129.2, 130.9, 132.7, 133.1, 134.2, 137.2, 137.5, 140.8, 153.3,

Synthesis Example 9. Synthesis of [Compound 9]

Synthesis Example 9-1) Synthesis of 2,2 '- (5-bromo-1,3-phenylene) bis (1,3,4-oxadiazole)

Scheme 9-1)

Bromo-3,5-diiodobenzene instead of 1,3-dibromo-5-iodobenzene used in Synthesis Example 8-1), (1,3,4-oxadiazole- 2-yl) boronic acid was used in an amount of 1.95 equivalents. (18 g, yield 72%).

Synthesis Example 9-2) Synthesis of [Compound 9]

The same procedure as in Synthesis Example 9-1) was repeated except for using 2- (5-bromo- [1,1'-biphenyl] -3-yl) -1,3,4-oxadiazole used in Synthesis Example 8-3) Synthesis of [Compound 9] was performed using the same method except that 2,2 '- (5-bromo-1,3-phenylene) bis (1,3,4-oxadiazole) Respectively. (4.1 g, yield 42%).

MS (MALDI-TOF): m / z 517 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

134.3, 125.3,

Synthesis Example 10. Synthesis of [Compound 10]

[Compound 10] was synthesized in the same manner as in Synthesis Example 2 except that 6-bromoquinoxaline was used instead of 6- (3-bromophenyl) quinoxaline used in Synthesis Example 2-2) (2.5 g, yield 51%).

MS (MALDI-TOF): m / z 449 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.3, 125.6, 126.1, 126.2, 127.1, 127.7, 127.9, 128.1, 128.2, 130.9, 132.7, 133.1, 134.2, 137.2, 139.7, 141.1, 142.7, 144.8 [

Synthesis Example 11. Synthesis of [Compound 11]

[Compound 11] was synthesized in the same manner as in Synthesis Example 3 except that 2-bromopyrimidine was used instead of 2- (4-bromophenyl) pyrimidine used in Synthesis Example 3-2) (2.8 g, yield 50%).

MS (MALDI-TOF): m / z 383 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

127.7,124,125.6,126.1,126.2,127.7,128.1,128.2,130.9,132.7,133.1,134.2,138.3,156.1,164.2 [28C]

Synthesis Example 12. Synthesis of [Compound 12]

Except that phenylboronic acid was used in place of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-2) ] Was synthesized (2.7 g, yield 41%).

MS (MALDI-TOF): m / z 457 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

127.6, 126.2, 127.2, 127.6, 127.7, 127.9, 128.1, 128.2, 129.2, 130.9, 132.5, 132.7, 133.1, 134.2, 137.2, 139.7, 140.8 [

Synthesis Example 13. Synthesis of [Compound 13]

Compound [13] was synthesized in the same manner as in Synthesis Example 2 except that 2-naphthalene boronic acid was used in place of 6-quinoxaline boronic acid used in Synthesis Example 2 (3.5 g, yield: 53%).

MS (MALDI-TOF): m / z 507 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.6, 126.1, 126.2, 126.8, 127.7, 128.1, 128.2, 129.7, 130.9, 132.7, 133.1, 134.2, 137, 137.2, 138.5 [

Synthesis Example 14. Synthesis of [Compound 14]

[Compound 14] was synthesized in the same manner as in Synthesis Example 4, except that 2-naphthaleneboronic acid was used instead of (1,8-naphthyridin-2-yl) boronic acid used in Synthesis Example 4-1) (2.5 g, yield 45%).

MS (MALDI-TOF): m / z 507 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

127.6, 126.1, 126.2, 127.2, 127.7, 128.1, 128.2, 130.9, 132.5, 132.7, 133, 133.1, 134.2, 137.2, 139.7 [

Synthesis Example 15. Synthesis of [Compound 15]

Except that 2-naphthaleneboronic acid was used instead of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid used in Synthesis Example 5-2) [Compound 15] was synthesized (2.4 g, yield 40%).

MS (MALDI-TOF): m / z 507 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.6, 126.1, 126.2, 126.8, 127.7, 128.1, 128.2, 129.7, 130.9, 132.7, 133.1, 134.2, 137, 137.2, 138.5 [

Synthesis Example 16. Synthesis of [Compound 16]

Was obtained in the same manner as in Synthesis Example 6, except that 9-phenanthreneboronic acid was used in place of (1,10-phenanthroline-5-yl) boronic acid used in Synthesis Example 6-2) ] Was synthesized (2.5 g, yield 50%).

MS (MALDI-TOF): m / z 753 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

124.1, 138.4, 124.3, 122.4, 124.7, 126.1, 126.2, 126.6, 126.8, 127.7, 128.1, 128.2, 128.3, 128.5, 129.7, 130.3, 131, 131.6, 131.9, 132.3, 132.7, 133.1, 133.8, 134.2, 136.6, 137, 147.3 [58C]

Synthesis Example 17. Synthesis of [Compound 17]

Compound [17] was synthesized in the same manner as in Synthesis Example 9, except that phenylboronic acid was used in place of (1,3,4-oxadiazol-2-yl) boronic acid used in Synthesis Example 9-1) (2.2 g, yield 41%).

MS (MALDI-TOF): m / z 533 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

125.1, 125.6, 126.1, 126.2, 127.6, 127.7, 127.9, 128.1, 128.2, 129.2, 130.9, 132.7, 133.1, 134.2, 137.2,

Synthesis Example 18. Synthesis of [Compound 18]

[Compound 18] was synthesized in the same manner as in Synthesis Example 10 except that 2-bromonaphthalene was used instead of 6-bromoquinoxaline used in Synthesis Example 10 (3.2 g, yield: 44%).

MS (MALDI-TOF): m / z 431 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

125.6, 126.1, 126.2, 127.7, 128.1, 128.2, 130.9, 132.7, 133.1, 134.2, 137.2 [

Synthesis Example 19. Synthesis of [Compound 19]

[Compound 19] was synthesized in the same manner as in Synthesis Example 11, except that bromobenzene was used instead of 2-bromopyrimidine in Synthesis Example 11 (4.1 g, yield 40%).

MS (MALDI-TOF): m / z 381 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

125.6, 126.1, 126.2, 127.6, 127.7, 127.9, 128.1, 128.2, 129.2, 130.9, 132.7, 133.1, 134.2, 137.2, 138.4 [

Examples 1 to 11

Manufacture of organic light-emitting diodes

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was allowed to have a pressure of 1 x 10 &lt; ^-7 &gt; torr and DNTD (700 ANGSTROM), NPD (300 ANGSTROM) (95 wt%) + [Formula 4] (5 wt%) (250 ANGSTROM) selected from the compound [19] and the compound [12] to [19] as the electron transport layer material, respectively (300 Å) were sequentially selected from [Compound 1] to [Compound 11], and LiF (10 Å) and Al (1,000 Å) were deposited in this order.

The structures of [Formula 4] and [Compounds 1] to [Compound 19] are as follows.

[Chemical Formula 4]

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19]

Example 12

Except that Liq (Lithium 8-hydroxy quinolate) corresponding to [Compound 3] prepared by the present invention in the electron transport layer and electron transport layer material conventionally used in the electron transport layer in a weight ratio of 50: 50 were mixed and used.

[Liq]

Example 13

Was prepared in the same manner as in Example 3, except that the following Formula 5 was used instead of the Formula 4 used in the light emitting layer.

[Chemical Formula 5]

Example 14

Was prepared in the same manner as in Example 3, except that the following Formula 6 was used instead of the Formula 4 used in the light emitting layer.

[Chemical Formula 6]

Comparative Example 1

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner as in Example 3, except that [Formula 7] was used instead of [Compound 12] used as a light emitting layer in Example 3. [

(7)

Comparative Example 2

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner except that Alq ₃ was used instead of [Compound 3] used as the electron transporting layer in Example 3.

[Alq ₃ ]

As shown in Table 1, in the case of an organic light emitting device comprising an anthracene derivative compound represented by the formula A according to the present invention as an electron transport layer and an anthracene derivative represented by the formula B as a host in the light emitting layer As compared with the organic light emitting device employing Alq _3, which is widely used as an electron transporting layer material, it can be seen that the low voltage driving can be performed by the improved electron transporting ability and the light emitting efficiency is excellent. Also, as shown in Comparative Example 1, , The use of the light emitting layer material represented by the general formula (B) as a host together with the material for the electron transporting layer represented by the general formula (A) enables a lower voltage driving than a light emitting layer material having a different structure as a host, As shown in Fig.

This is because, in the case of an organic light emitting device including an anthracene derivative compound having a similar skeleton form according to the present invention in an electron transporting layer and a light emitting layer, the organic light emitting device can be driven at a lower voltage than when a material having an electron transporting layer material similar to that of a light emitting layer material is used And exhibits a better luminous efficiency than that of the organic light emitting device.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (18)

An organic light emitting device comprising an electron transporting layer and a light emitting layer between a first electrode and a second electrode, wherein the electron transporting layer contains one or more anthracene derivatives selected from compounds represented by the following formula (A) And an organic compound represented by the formula (B).
(A)

In the above formula (A)
L ₁ is

or

Lt;
Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero ring having 1 to 50 carbon atoms An aryl group, or a substituted or unsubstituted C1 to C30 silyl group;
Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI &gt;group;
m and m 'are integers of 1 to 8;
When the substituents Y and Z are not bonded to the carbon of the aromatic ring of the naphthyl group or the anthracenyl group, hydrogen is bonded;
X ₁ to X ₅ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6- Substituted or unsubstituted C1 to C30 aryl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C20 alkynyl groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, , A heteroaryl group having 2 to 50 carbon atoms having N or S, a cyano group, a nitro group, and a halogen group,
At least one of X ₁ , X ₂ X ₄ , and X ₅ is a heteroaryl group having 2 to 20 carbon atoms including a nitrogen atom;
And X ₆ is a heteroaryl group having 2 to 20 carbon atoms containing a nitrogen atom.
[Chemical Formula B]

In the above formula (B)
Y, Z, m and m 'are the same as defined in the above formula (A)
L ₂ is

or

Lt;
Wherein Q ₁ to Q ₅ are the same or different from each other and independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 6 or more carbon atoms Substituted or unsubstituted C1 to C30 aryl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C20 alkynyl groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, A cycloalkenyl group having 5 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,
Q ₆ is an aryl group having 6 to 20 carbon atoms;
When the substituent L ₂ in the compound represented by the formula (B) is Q ₆ , the substituent L ₁ in the compound represented by the formula (A) is X ₆ ,
When the substituent L ₂ in the compound represented by the formula (B) is

, The substituent L &lt; ₁ &gt; in the compound represented by the above formula (A)

At least one of the substituents Q _1, Q ₂ , Q ₄ and Q ₅ in the compound represented by the formula (B) is an aryl group having 6 to 20 carbon atoms, and the number of the aryl groups having 6 to 20 carbon atoms and the phenyl group where the bond at a position same as that of the aromatic carbon position in the phenyl group count and group the heteroaryl coupling having 2 to 20 hetero aryl groups containing a substituent of a nitrogen atom that is bonded to the phenyl group of L ₁ in the general formula a The aryl group having 6 to 20 carbon atoms is bonded to the phenyl group of the formula (B)
The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
When at least one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the compound represented by the formula (A) used in the electron transport layer is a heteroaryl group having 2 to 20 carbon atoms and contains a nitrogen atom, Wherein the aryl group is any one substituent selected from Structural Formulas 1 to 6. &lt; Desc / Clms Page number 24 &gt;
[Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

In Structural Formulas 1 to 6
T ₁ to T ₈ are the same or different and independently selected from the group consisting of C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ), O and S;
R ₁ to R ₁₃ are the same or different from each other and independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S,
In each of Structural Formulas ₁ to 6, one of R ₁ to R ₁₃ is a single bond forming a bond with the phenyl group of the substituent L ₁ in Formula A above. 3. The method of claim 2,
Y and Z of formula (A) are the same or different, and independently of each other, hydrogen, deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; , And m and m 'are each an integer of 1 to 4, The method of claim 3,
The substituents X ₁ , X &lt; ₂ &gt;, X &lt; ₄ &gt;, and X &lt; ₅ &gt; are any one substituent selected from the structural formulas 1 to 6. [ 5. The method of claim 4,
Wherein the substituents in the structural formulas 1 to 6 each independently represent a heteroaryl group by substituting one to three nitrogen atoms at an aromatic carbon position in the substituent. 3. The method of claim 2,
Wherein X ₆ in the substituent L ₁ is any one substituent selected from the group consisting of the structural formulas 1 to 6. The method according to claim 1,
The substituents X ₁ , Wherein at least one of X ₂ , X ₄ , and X ₅ is any one of substituents 101 to 606 shown below.
[Substituent 101] [Substituent 102] [Substituent 103]

[Substituent group 104] [Substituent group 105] [Substituent group 106]

[Substituent group 107] [Substituent group 108] [Substituent group 109]

[Substituent group 110] [Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent 207] [Substituent 208]

[Substituent group 301] [Substituent group 302] [Substituent group 303]

[Substituent group 304] [Substituent group 305] [Substituent group 306]

[Substituent group 307] [Substituent group 308]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent group 404] [Substituent group 405] [Substituent group 406]

[Substituent group 407] [Substituent group 408] [Substituent group 409]

[Substituent group 410] [Substituent group 411] [Substituent group 412] [Substituent group 413]

[Substituent group 501] [Substituent group 502] [Substituent group 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, A substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each of May be fused to adjacent groups to form a ring,
n is an integer of 0 to 9,
When the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of the substituents 101 to 606, hydrogen is bonded,
One of the Rs is a single bond bonded to the phenyl group of the substituent L &lt; ₁ &gt; in the [formula (A)]. 8. The method of claim 7,
The substituent X &_lt; ₁ &gt; of L &lt; ₁ & X ₂ , X ₄ , and X ₅ is any one substituent selected from the substituents 101 to 606. 9. The method according to any one of claims 1 to 8,
Since the organic luminescent device has the same structure except for the substituent L ₁ in the compound represented by the formula A used in the electron transport layer and the substituent L ₂ in the compound represented by the formula B used in the emitting layer, , And the compound represented by the formula (A) and the compound represented by the formula (B) in the organic light emitting device are different from each other only in the substituents L ₁ and L ₂ bonded to the anthracenyl group. delete The method according to claim 1,
Only _one of the substituents X ₁ , X ₂ , X ₄ and X ₅ in the formula (A) is a heteroaryl group having 2 to 20 carbon atoms, and only one of the substituents Q ₁ , Q ₂ , Q ₄ and Q ₅ in the formula Wherein the organic group is an aryl group having 6 to 20 carbon atoms. The method according to claim 1,
Wherein the organic light emitting device further comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, and an electron injecting layer. The method according to claim 1,
Wherein the light emitting layer is made of a host and a dopant, and the organic light emitting material is used as a host material. The method according to claim 1,
Wherein the electron transport layer is a mixture of a compound represented by the formula (A) and an electron transport compound different from the compound represented by the formula (A) 15. The method of claim 14,
Wherein the electron transporting layer has a mixing ratio of a compound represented by the formula (A) and an electron transporting compound different from the compound represented by the formula (A) in the range of 10: 90 to 90: Organic light emitting device 16. The method of claim 15,
Wherein the other electron-transporting compound is a compound represented by the following formula (C)
&Lt; RTI ID = 0.0 &

In the above formula (C)
Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,
O is oxygen,
A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,
M is 1 and n is 0 when M is a metal selected from an alkali metal,
M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,
M is from 1 to 3 when M is boron or aluminum, and n is any of from 0 to 2, and m + n = 3;
Y are each the same or different and independently selected from the following formulas [C1] to [C39].
[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,
R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And adjacent substituents may be connected to alkylene or alkenylene to form a spiro ring or a fused ring.
Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term &quot; substituted aryl group &quot; 13. The method according to claim 1 or 12,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. The method according to any one of claims 1 to 8, 11 to 16,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device, characterized in that the organic light-emitting device

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