KR101676416B1 - Organic compound and organic optoelectric device and display device - Google Patents

Abstract

상기 화학식 1에서, X, L, R1 내지 R⁸은 명세서에서 정의한 바와 같다.An organic optoelectronic device including the organic compound, and a display device.
[Chemical Formula 1]

In Formula 1, X, L, R 1 to R ⁸ are as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound, an organic optoelectronic device,

Organic optoelectronic devices, and display devices.

 Organic optoelectronic devices are devices that can switch between electrical and optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, And a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic layer is highly affected by the organic material contained in the organic layer.

In particular, in order for the organic light emitting device to be applied to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing the electrochemical stability.

One embodiment provides an organic compound capable of providing a high-efficiency and long-lived organic optoelectronic device.

Another embodiment provides an organic optoelectronic device comprising the organic compound.

Another embodiment provides a display device comprising the organic opto-electronic device.

According to one embodiment, there is provided an organic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

X is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups or combinations thereof,

L is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Substituted or unsubstituted C3 to C30 heteroarylene groups, substituted or unsubstituted C6 to C30 arylene amine groups, substituted or unsubstituted C6 to C30 heteroarylene amine groups, substituted or unsubstituted C1 to C30 alkoxy A substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R ¹ to R ⁸ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof.

According to another embodiment, there is provided an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer includes the organic compound.

The organic layer may include a light emitting layer, and the light emitting layer may include the organic compound.

The organic compound may be included as a host of the light emitting layer.

The organic layer may include at least one auxiliary layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer, have.

According to another embodiment, there is provided a display device including the organic opto-electronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, A C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heteroaryl group, a C1 to C20 alkoxy group , A C1 to C10 trifluoroalkyl group such as a fluoro group or a trifluoromethyl group, or a cyano group.

A substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group or a trifluoromethyl group, Two adjacent substituents may be fused to form a ring. For example, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

Means one to three heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon unless otherwise defined .

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

The term "aryl group" used herein means a substituent in which all the elements of the cyclic substituent have p-orbital and the p-orbital forms a conjugation, and the monocyclic or fused-ring polycyclic (I. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

As used herein, the term "heteroaryl group" means that the aryl group contains 1 to 3 hetero atoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, A substituted or unsubstituted aryl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group , A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group , A substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazine group, a substituted or unsubstituted Thiazine group, may be a substituted or unsubstituted phenoxazine group, a substituted or unsubstituted fluorenyl group, or a combination thereof, are not limited.

In the present specification, the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer. More specifically, it may be similar to the characteristic of pushing electrons.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement. More specifically, it may be similar to the characteristic of attracting electrons.

The organic compounds according to one embodiment will be described below.

The organic compound according to one embodiment is represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups or combinations thereof,

L is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Substituted or unsubstituted C3 to C30 heteroarylene groups, substituted or unsubstituted C6 to C30 arylene amine groups, substituted or unsubstituted C6 to C30 heteroarylene amine groups, substituted or unsubstituted C1 to C30 alkoxy A substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R ¹ to R ⁸ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof.

The organic compound represented by Formula 1 has two carbazole groups and has a structure in which carbon of one carbazole group and nitrogen of another carbazole group are directly bonded at specific positions.

According to the structure, it is possible to reduce the resonance in the organic compound to increase the triplet energy (T1), thereby improving the efficiency of the organic optoelectronic device to which the organic compound is applied. The triplet energy (T1) may also have a range suitable for use as, for example, a phosphorescent host, such as about 2.6 to 2.9 eV.

Also, the deposition temperature can be lowered by effectively reducing the stacking of the organic compounds according to the structure. Accordingly, the organic compound deposition process can be performed at a relatively low temperature, thereby improving the processability.

In addition, thermal stability can be enhanced according to the structure, and thus it is possible to prevent the organic compound from being deteriorated by heat generated during the process or driving the device to which the organic compound is applied. Therefore, the lifetime of the organic compound and the device to which the organic compound is applied can be improved.

The organic compound represented by Formula 1 may be designed to have desired characteristics by having various functional groups and / or substituents. For example, when X in the above formula (1) is a functional group having a hole property, the organic compound can be designed as a compound having a strong hole characteristic. For example, when X in the formula (1) is a functional group having an electron characteristic, It can be designed as a compound having both amphipathic characteristics by including both the branch portion and the hole portion.

In Formula 1, X may be selected from, for example, a substituted or unsubstituted functional group listed in Group 1 below.

[Group 1]

In the group 1,

Y is N, O, S, SO ₂ , NR ^a , CR ^b , SiR ^c , CR ^d R ^e or SiR ^f R ^g ,

Z is N, CR ^h , CR ⁱ R ^j or NR ^k ,

Wherein R ^a to R ^j are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl An amino group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonyl An amino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C20 acyl group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A halogen atom, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a perorenyl group or a substituted or unsubstituted C1 to C30 heteroarylthiol group It is a combination.

In the group 1, "*" is a point connected to L in the formula (1), and may be located in any one of the elements forming the functional group. For example, a carbon or a heteroatom which constitutes the functional group or the substituent of the functional group.

X may be represented, for example, by any one of the following formulas A1 to A8.

[Formula A1] [Formula A2] [Formula A3] [Formula A4]

[Chemical formula A5] [Chemical formula A8] [Chemical formula A8] [Chemical formula A8]

In the above formulas A1 to A8,

R ¹⁰⁰ to R ¹⁰⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or combinations thereof .

The X may be represented, for example, by any one of the following formulas A9 to A22.

(A10) < / RTI > (A12) < RTI ID = 0.0 &

(A16) < RTI ID = 0.0 > (A16) < / RTI &

[화학식 A17] [화학식 A18] [화학식 A19] [화학식 A20]

(A19) < RTI ID = 0.0 > (A20) < / RTI &

(A21) < EMI ID =

In the above formulas A9 to A22,

R ¹⁰⁴ to R ¹⁰⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or combinations thereof .

X may be represented, for example, by any one of the following formulas A23 to A33.

 (A25) < RTI ID = 0.0 > (A25) < / RTI &

[화학식 A27] [화학식 A28] [화학식 A29] [화학식 A30]

[Chemical Formula A29] [Chemical Formula A29] [Chemical Formula A29] [Chemical Formula A30]

(A33) [Formula A32] [Formula A33] [Formula A34]

In the above formulas A23 to A34,

R ¹⁰⁴ to R ¹¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or combinations thereof .

X may be represented, for example, by any one of the following formulas A35 to A37.

(A37) < / RTI >

In the above formulas A35 to A37,

Y1 is N, CR ^b Or SiR ^c ego,

Y 2 is O, S, SO ₂ , NR ^a , CR ^d R ^e or SiR ^f R ^g ,

Wherein each of R ^a to R ^g is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, ego,

R ¹¹⁴ to R ¹²¹ each independently represents hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or combinations thereof .

The X may be represented, for example, by any one of the following formulas A38 to A46.

(A40) < / RTI > < RTI ID = 0.0 >

[Chemical Formula A41] [Chemical Formula A42]

[Chemical Formula A43] [Chemical Formula A44]

[Chemical Formula A45] [Chemical Formula A46]

In the above formulas A38 to A46,

R ¹²² to R ¹³¹ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or combinations thereof .

In the formula (1), L is a linking group connecting the carbazole group and the functional group (X), and the conjugation length of the entire compound can be determined, from which the triplet energy bandgap can be controlled. It is also possible to control the triplet energy by changing the binding position of ortho, para, and meta.

The L may be, for example, a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C3 to C30 heteroarylene group.

When L is an arylene group or a heteroarylene group, for example, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted p-terphenylene group, a substituted or unsubstituted m-terphenyl Substituted or unsubstituted naphthylene group, substituted or unsubstituted anthracenylene group, substituted or unsubstituted phenanthrylene group, substituted or unsubstituted pyrenylene group or substituted Or an unsubstituted fluorenylene group.

In Formula 1, R ¹ to R ⁸ each independently represent, for example, hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heteroaryl group have.

When R ¹ to R ⁸ are each independently an arylene group or a heteroarylene group, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted fluorenyl group.

The organic compound may be, for example, compounds listed in the following Group 2, but is not limited thereto.

[Group 2]

Hereinafter, the organic optoelectronic device to which the organic compound is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

FIG. 1 or 2 is a cross-sectional view illustrating an organic light emitting device according to one embodiment.

1, an organic optoelectronic device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al and BaF ₂ / Ca.

The organic layer 105 includes the light-emitting layer 130 including the above-described organic compound.

The light-emitting layer 130 may include, for example, the organic compound alone, or may be a mixture of at least two of the organic compounds described above, or may include a mixture of the above-described organic compound and another compound. When the above-mentioned organic compound is mixed with another compound, it may be contained in the form of, for example, a host and a dopant, and the above-mentioned organic compound may be included, for example, as a host. The host may be, for example, a phosphorescent host or a fluorescent host, for example, a phosphorescent host.

When the above-mentioned organic compound is included as a host, the dopant may be an inorganic, organic, or organic compound and may be selected from known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The organic compound described above may be included in the light emitting layer 130 and / or the hole auxiliary layer 140. 1 or 2, the organic layer 105 may further include an electron injection layer, an electron transport layer, an auxiliary electron transport layer, an auxiliary hole transport layer, a hole transport layer, a hole injection layer, and combinations thereof have.

1 and 2, the light emitting layer 130, the hole transporting layer 140, and the electron injecting layer, the auxiliary electron transporting layer, the electron transporting layer, the major transporting layer, the auxiliary transporting layer 140, , A hole injection layer, and a combination thereof, includes a compound for the organic optoelectronic device. In addition, the compound for an organic optoelectronic device of the present invention can be contained in the light emitting layer and can be used as a host in the light emitting layer.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The organic light emitting device described above can be applied to an organic light emitting display.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

Synthesis of intermediate product

Step 1: Synthesis of intermediate product (A)

1,3-dichloro-2-nitro 25.2g (131.25 mmol), phenyl beam Nick Acid _{16.0g (131.25 mmol), K 2} CO 3 23.58g (170.63 mmol), Pd (PPh 3) 4 1.52g (1.31 mmmol ) Was suspended in 300 ml of toluene and 150 ml of distilled water, followed by reflux stirring for 12 hours under a nitrogen stream. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, distilled under reduced pressure, and recrystallized from methanol to obtain 27.4 g of an intermediate product (A). The yield was 89%.

Step 2: Synthesis of intermediate product (B)

3.14 g (3.42 mmmol) of Pd ₂ (dba) ₃ were dissolved in 400 ml of toluene, and the mixture was stirred at room temperature for 10 minutes. After suspending, 1.66 mL (6.85 mmol) of P (t-Bu) ₃ was added and the mixture was stirred under reflux for 24 hours under a nitrogen stream. The mixture is then extracted with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. Subsequently, the organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v) to obtain 24.33 g of intermediate product (B). The yield was 78%.

Step 3: Synthesis of intermediate product (C)

24.0 g (65.86 mmol) of the intermediate product (B) and 57.3 mL (329.31 mmol) of triethylphosphite were stirred under reflux for 5 hours in a nitrogen stream. After completion of the reaction, the reaction solvent was removed and silica column chromatography was performed with hexane: dichloromethane = 6: 4 (v / v) to obtain 9.19 g of intermediate product (C). The yield was 42%.

Synthesis of organic compounds

The organic compound of the present invention was synthesized by the following method.

Intermediate product (C), the substituents compound (Ax, x is a halogen atom), then suspended in NaO (t-Bu) and Pd ₂ (dba) ₃ in toluene was put into the P (t-Bu) ₃ 24 hours in a nitrogen gas stream Lt; / RTI > The mixture was then extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. Subsequently, the organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane (1: 1 v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain an organic compound.

The synthesized organic compounds are listed in Table 1.

* Temperature: The temperature at which the organic compound is deposited to a thickness of 1 Å.

Comparative compound

[Comparative Compound 1] [Comparative Compound 2]

[Comparative compound 3] [Comparative compound 4]

Evaluation 1: Determination of energy level of organic compounds

The triplet energies (T1) of the organic compounds obtained in Synthesis Examples 1 to 11 were measured and compared with the triplet energies (T1) of the comparative compounds 1 to 4. Triplet energy (T1) can be compared between compounds having the same or similar substituents, and Synthesis Examples 1 to 7 and Comparative Compounds 1 and 2 can be compared, and Synthesis Examples 8 to 11 and Comparative Compounds 3 and 4 can be compared.

Triplet energy (T1) was measured using a fluorescence spectrophotometer (Hitachi F-4500).

The results are shown in Table 2 and Table 3.

Tables 2 and 3 show that triazole energy (T1) is higher than that when carbazole is substituted at the ortho position of the compound of the present invention at the meta or para position have.

Fabrication of organic light emitting device

Example  One

The glass substrate coated with ITO (Indium tin oxide) 1500 Å thin film was cleaned with distilled water ultrasonic waves. It was then ultrasonically washed with isopropyl alcohol, acetone and methanol and dried. Subsequently, the substrate was cleaned using oxygen plasma for 5 minutes to form an ITO transparent electrode. Subsequently, a compound represented by the following formula (A) was vacuum deposited on the ITO transparent electrode to form a hole assist layer having a thickness of 1200 Å.

(A)

The material synthesized in Synthesis Example 1 was used as a host on the hole-assist layer, doped with 7 wt% of a compound represented by the following formula (B) as a phosphorescent green dopant, and a 300Å thick light emitting layer was formed by vacuum deposition.

[Chemical Formula B]

(2-methyl-8-quinolinolato-N1,08) -1,1'-biphenyl-4-olato) aluminum represented by the following formula (C) (8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum, BAlq) ) aluminum, Alq3] 250Å were successively deposited to form an electron-assisted layer. An organic light-emitting device was fabricated by forming a cathode by sequentially vacuum-depositing LiF 5Å and Al 1000Å on the electron-assisted layer.

[Chemical formula C] [Chemical formula D]

Example  2

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 2 was used instead of the organic compound obtained in Synthesis Example 1.

Example  3

An organic light emitting device was fabricated in the same manner as in Example 1 except that the organic compound obtained in Synthesis Example 3 was used in place of the organic compound obtained in Synthesis Example 1. [

Example  4

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 4 was used in place of the organic compound obtained in Synthesis Example 1.

Example  5

An organic light-emitting device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 5 was used in place of the organic compound obtained in Synthesis Example 1.

Example  6

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 6 was used in place of the organic compound obtained in Synthesis Example 1.

Example  7

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 7 was used in place of the organic compound obtained in Synthesis Example 1.

Example  8

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 8 was used in place of the organic compound obtained in Synthesis Example 1.

Example  9

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 9 was used in place of the organic compound obtained in Synthesis Example 1.

Example  10

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 10 was used in place of the organic compound obtained in Synthesis Example 1.

Example  11

An organic luminescent device was fabricated in the same manner as in Example 1, except that the organic compound obtained in Synthesis Example 11 was used in place of the organic compound obtained in Synthesis Example 1.

Comparative Example  One

An organic luminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound 1 was used instead of the organic compound obtained in Synthesis Example 1.

Comparative Example  2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Comparative Compound 2 was used instead of the organic compound obtained in Synthesis Example 1. [

Comparative Example  3

An organic luminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound 3 was used instead of the organic compound obtained in Synthesis Example 1.

Comparative Example  4

An organic luminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound 4 was used instead of the organic compound obtained in Synthesis Example 1.

Rating 2

The luminous efficiency and lifetime characteristics of the organic luminescent devices according to Examples 1 to 11 and Comparative Examples 1 to 4 were evaluated.

The evaluation method is as follows (1) to (3).

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current value flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light emitting device manufactured, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

The results are shown in Tables 4 and 5.

According to Tables 4 and 5, it was confirmed that the organic luminescent devices according to Examples 1 to 7 were superior in luminous efficiency and lifespan characteristics to the organic luminescent devices according to Comparative Examples 1 and 2, It can be seen that the organic light emitting device is superior in luminous efficiency and lifetime characteristics to the organic light emitting device according to Comparative Examples 3 and 4.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100, 200: Organic light emitting device
105: organic layer 110: cathode
120: anode 130: light emitting layer
140: hole assist layer

Claims (13)

An organic compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
X is represented by any one of the following formulas A5 to A8, A14 to A25, A27 to A29, A32 to A34, A45 and A46,
L is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

[Chemical formula A5] [Chemical formula A8] [Chemical formula A8] [Chemical formula A8]

[A14] [Formula A15] [Formula A16]

(A19) < RTI ID = 0.0 > (A20) < / RTI &

(A21) < EMI ID =

[Chemical Formula A23] [Chemical Formula A24] [Chemical Formula A25]

(A29) [Formula A28] [Formula A29]

(A32) < / RTI >< RTI ID = 0.0 >

[Chemical Formula A45] [Chemical Formula A46]

In the above formulas A5 to A8, A14 to A25, A27 to A29, A32 to A34, A45 and A46,
Each of R ¹⁰¹ to R ¹¹³ and R ¹²² to R ¹³¹ independently represents hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof.
delete delete delete delete delete delete The method of claim 1,
An organic compound selected from the compounds listed in Group 2 below:
[Group 2]

The positive and negative electrodes facing each other,
At least one organic layer positioned between the anode and the cathode,
/ RTI >
Wherein the organic layer comprises the organic compound according to any one of claims 1 to 8.
The method of claim 9,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the organic compound.
11. The method of claim 10,
Wherein the organic compound is included as a host of the light emitting layer.
The method of claim 9,
Wherein the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer,
Wherein the auxiliary layer comprises the organic compound
Organic optoelectronic devices.
A display device comprising the organic opto-electronic device according to claim 9.

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