KR20160049842A - Organic optoelectric device and display device - Google Patents

Abstract

The present invention relates to an organic optoelectronic device and a display device comprising the organic optoelectronic device. The organic optoelectronic device comprises: an anode and a cathode facing each other; a light emitting layer placed between the anode and the cathode; an electron transport layer placed between the cathode and the light emitting layer; and an auxiliary electron transport layer placed between the electron transport layer and the light emitting layer, wherein the auxiliary electron transport layer comprises at least one type of first compounds represented by chemical formula 1. The chemical formula 1 is the same as described in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to 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.

One of the biggest problems in long life full color displays is the lifetime of blue organic light emitting devices. Therefore, much research is underway to develop a long-lived blue organic light-emitting device. In order to solve such a problem, the present invention provides a long-life blue organic light emitting device.

One embodiment provides an organic optoelectronic device capable of realizing high efficiency characteristics.

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

According to one embodiment, there is provided an electron transporting structure comprising an anode and a cathode facing each other, a light emitting layer positioned between the anode and the cathode, an electron transporting layer positioned between the cathode and the light emitting layer, Layer, wherein the electron transport-facilitating layer comprises at least one first compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Each Z is independently N, C or CR ^a ,

At least one of Z is N,

R ¹ to R ⁶ , and R ^a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A combination thereof,

L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group or a combination thereof,

n1 to n6 each independently represent an integer of 0 to 5;

According to another embodiment, there is provided a light emitting device comprising: an anode and a cathode facing each other; a light emitting layer positioned between the anode and the cathode; a hole transporting layer positioned between the anode and the light emitting layer; a hole transporting auxiliary layer disposed between the hole transporting layer and the light emitting layer; An electron transporting layer positioned between the cathode and the light emitting layer, and an electron transporting layer positioned between the electron transporting layer and the light emitting layer, wherein the electron transporting layer comprises at least one first Wherein the hole transporting auxiliary layer comprises at least one second compound represented by the following general formula (2).

[Chemical Formula 1]

In the above formula (1), the definitions of Z, R ¹ to R ⁶ , L ¹ to L ⁶ , and n ¹ to n ⁶ are as described above,

(2)

In Formula 2,

X < ¹ > is O or S,

R ⁷ to R ⁹ each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 C30 aryloxy groups, substituted or unsubstituted C6 to C30 arylthio groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C2 to C30 amino groups, substituted or unsubstituted C3 to C30 silyl groups , A cyano group, a nitro group, a hydroxyl group or a carboxyl group, or a combination thereof,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,

L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,

n7 to n9 each independently represent an integer of 0 to 3,

"Substitution" in the above formulas (1) and (2) means that at least one hydrogen is substituted with a substituent selected from the group consisting of a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, C30 alkyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, C1 to C10 trifluoroalkyl group or cyano group ≪ / RTI >

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

A high-efficiency organic optoelectronic device can be realized.

1 and 2 are cross-sectional views schematically showing an organic optoelectronic device according to one embodiment.

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 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl 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 C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group and 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, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group. 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.

As used herein, the term " aryl group "means a substituent in which all the elements of the cyclic substituent have p-orbital, and these p-orbital forms a conjugation, and monocyclic, Fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term "heterocyclic group" means a heteroatom selected from the group consisting of N, O, S, P and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Containing at least one and the remainder being carbon. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms. Therefore, the heterocyclic group is a superordinate concept including a heteroaryl group.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra 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 pyrenyl 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 thiazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted thiazolyl group, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted thiazinyl groups, substituted or unsubstituted benzofuranyl groups, substituted or unsubstituted benzothiophenyl groups, substituted or unsubstituted benzimidazolyl groups, substituted A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl 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, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted phenazinyl groups, Substituted or unsubstituted dibenzothiocarbonyl groups, substituted or unsubstituted dibenzothiocarbonyl groups, substituted or unsubstituted dibenzothiocarbonyl groups, substituted or unsubstituted dibenzothiocarbonyl groups, substituted or unsubstituted dibenzothiocarbonyl groups, A phenyl group, a combination thereof, or a combination thereof may be in a fused form, but is not limited thereto.

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.

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.

Hereinafter, an organic optoelectronic device according to one embodiment 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, the organic light emitting device, which is an example of the organic optoelectronic device, is exemplarily described, but the present invention is not limited thereto and can be applied to other organic optoelectronic devices as well.

In the drawings, the thickness is enlarged to clearly represent the layers and regions. Like parts are designated with like reference numerals throughout the specification. Whenever a portion of a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. Conversely, when a part is "directly over" another part, it means that there is no other part in the middle.

1 and 2 are cross-sectional views schematically showing an organic optoelectronic device according to one embodiment.

Referring to FIG. 1, an organic optoelectronic device according to one embodiment includes an anode 10 and a cathode 20 facing each other, and an organic layer 30 positioned between the anode 10 and the cathode 20.

The anode 10 can be made of a conductor having a high work function to facilitate, for example, hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 10 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 SnO2 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 20 may be made of a conductor having a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide, and / or a conductive polymer. The cathode 20 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, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

The organic layer 30 includes a hole transporting layer 31, a light emitting layer 32 and a hole transporting auxiliary layer 33 located between the hole transporting layer 31 and the light emitting layer 32.

An electron transporting layer 34 and an electron transporting layer 35 disposed between the electron transporting layer 34 and the light emitting layer 32. The electron transporting layer 34 is formed of a metal such as aluminum,

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and may include an electron injection layer 37 between the electron transport layer 34 and the cathode 20. [ And may further include an injection layer 36.

The hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 not only improves the interface characteristics between the ITO used as the anode and the organic material used as the hole transport layer 31, It is applied on the top of uneven ITO to soften the surface of ITO. For example, in order to control the difference between the work function level of ITO that can be used as an anode and the HOMO level of the hole transport layer 31, the hole injection layer 37 has a function of the ITO function and the HOMO level of the hole transport layer 31 As a substance having a medium value, a substance having a particularly suitable conductivity is selected. As a constituent material of the positive hole injection layer 37, N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol- Diamine (N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'-diamine) may be used. (CuPc), N, N'-dinaphthyl-N, N'-phenyl- (1,1'-diphenylphosphonium), and the like can be used together with the conventional materials constituting the hole injection layer 37. [ 4,4'-diamine, NPD), 4,4 ', 4 "-tris [methylphenyl (phenyl) amino] triphenyl amine (m- (phenylamino) triphenyl amine (1-TNATA), 4,4 ', 4 "-tris [2-naphthyl (4-diphenylaminophenyl) phenylamino] benzene (p-DPA-TDAB) and the like, as well as aromatic amines such as 4,4'- Poly (3,4-ethylenedioxythiophene) -poly (styrnesulfonate) (PEDOT) which is a polythiophene derivative as a conductive polymer can be used as a conductive polymer. The hole injection layer 37 may be coated on top of the ITO used as the anode, for example, with a thickness of 10 to 300 ANGSTROM.

The electron injection layer 36 is a layer that is stacked on top of the electron transport layer and facilitates injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer 36 may be used without any particular limitation as long as it is commonly used in the art And materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

The hole transport layer 31 is a layer for facilitating hole transport from the anode 10 to the light emitting layer 32, for example, an amine compound, but is not limited thereto.

The amine compound may comprise, for example, at least one aryl group and / or heteroaryl group. The amine compound can be represented, for example, by the following formula (a) or (b), but is not limited thereto.

[Formula a] [Formula b]

In the above formula (a) or (b)

Each of Ar ^a to Ar ^g is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof ,

At least one of Ar ^a to Ar ^c and at least one of Ar ^d to Ar ^g is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group,

Ar ^h is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

The electron transport layer 34 is a layer for facilitating the electron transfer from the cathode 20 to the light emitting layer 32. The electron transport layer 34 is formed of an organic compound having an electron withdrawing group, , Or a mixture thereof can be used. For example, aluminum trihydroxyquinoline (Alq ₃ ), a 1,3,4-oxadiazole derivative, 2- (4-biphenyl-5-phenyl-1,3,4-oxadiazole (4-biphenylyl) -5-phenyl-1,3,4-oxadiazole, PBD), a quinoxaline derivative such as 1,3,4-tris [(3-phenyl-6-trifluoromethyl) (4-tris [(3-penyl-6-trifluoromethyl) quino-xaline-2-yl] benzene, TPQ), triazole derivatives and triazine derivatives, Yl) phenyl) quinoline (8- (4- (4- (naphthalen-3-yl) -1,3,5-triazin- 2-yl) -6- (naphthalen-3-yl) -1,3,5-triazin-2-yl) phenyl) quinoline.

The electron transporting layer may be used alone or in combination with the electron transporting layer material as the organometallic compound represented by the following formula (c).

(C)

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 5 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;

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In the present invention, each Y may be the same or different and independently selected from the following formulas c1 to c39, but is not limited thereto.

[Chemical formula c1] [Chemical formula c2] Chemical formula c3 Chemical formula c4 Chemical formula c5 [

[Chemical formula c6] [Chemical formula c7] [Chemical formula c8] [Chemical formula c9] [Chemical formula c10]

[Chemical formula c11] [Chemical formula c12] Chemical formula c13] Chemical formula c14] Chemical formula c15]

 [Chemical formula c16] [Chemical formula c17] [Chemical formula c18] [Chemical formula c19] [Chemical formula c20]

[Chemical formula c22] Chemical formula c22 Chemical formula c24 Chemical formula c25 [

[Chemical Formula c26] Chemical Formula c27 Chemical Formula c29 Chemical Formula c30 [

[Chemical formula c32] Chemical formula c33 Chemical formula c34 Chemical formula c35 [

[Chemical formula c36] [Chemical formula c37] Chemical formula c38] Chemical formula c39]

In the above formulas c1 to c39,

R is identical or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C3 to C30 hetero A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkylamino group, A substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylamino group, and a substituted or unsubstituted C6 to C30 arylsilyl group, and is connected to an adjacent substituent by an alkylene or alkenylene to form a spiro ring or a fused ring A ring can be formed.

The light emitting layer 32 is an organic layer having a light emitting function, and includes a host and a dopant when a doping system is employed. At this time, the host has a function of promoting the recombination of electrons and holes mainly, and has a function of confining excitons in the light emitting layer, and the dopant has a function of efficiently emitting excitons obtained by recombination.

The light emitting layer may include a known host and a dopant.

Examples of the known host include Alq3, CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) (N, N-phenylbenzimidazole-2-yl) benzene), anthracene (ADN), TCTA, TPBI (1,3,5-tris ), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), mCP, OXD-7 and BH113 commercially available from SFC.

The dopant may be at least one of a fluorescent dopant and a phosphorescent dopant. The phosphorescent dopant may be an organic metal complex including Ir, Pt, Os, Re, Ti, Zr, Hf or a combination of two or more of them, but is not limited thereto.

Examples of known blue dopants include F ₂ Irpic, (F ₂ ppy) ₂ Ir (tmd), Ir (dfppz) ₃ , ter-fluorene, 4,4'- BD370 commercially available from DPVBi, 2,5,8,11-tetra- tert -butylperylene (TBPe), DPVBi, pyrene derivatives (KR0525408, LG Electronics Co., Ltd.), BD01, But is not limited thereto.

            DPAVBi TBPe

(KR0525408, LG Electronics Co., Ltd.)

Examples of known red dopants include, but are not limited to, PtOEP, Ir (piq) ₃ , BtpIr, and the like.

Examples of a known green _{dopant, Ir (ppy) 3 (ppy} = phenylpyridine), and the like, but _{Ir (ppy) 2 (acac)} , Ir (mpyp) 3, but is not limited to such.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from the range of about 0.01 to about 15 wt% per 100 wt% of the light emitting layer, but is not limited thereto.

The thickness of the light emitting layer is about 200 ANGSTROM to about 700 ANGSTROM.

The electron transporting auxiliary layer (35) comprises at least one first compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Each Z is independently N, C or CR ^a ,

At least one of Z is N,

R ¹ to R ⁶ , and R ^a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A combination thereof,

L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group or a combination thereof,

n1 to n6 each independently represent an integer of 0 to 5;

Since the first compound includes a ring containing at least one nitrogen, the structure becomes susceptible to electrons upon application of an electric field, and the electron injection amount is increased, thereby lowering the driving voltage of the organic optoelectronic device to which the first compound is applied And the efficiency can be improved.

In one embodiment of the present invention, n1 to n6 are each independently an integer of 0 to 5, and n1 + n2 + n3 + n4 + n5 + n6? 1, and n1 + n2 + n3 + n4 + n5 + , n1 + n2 + n3 + n4 + n5 + n6? 3, and n1 + n2 + n3 + n4 + n5 + n6? N1 + n2 + n3 + n4 + n5 + n6? 15, n1 + n2 + n3 + n4 + n5 + n6? 12, n1 + n4 + n5 + n6? 8, n1 + n2 + n3 + n4 + n5 + n6? 7, n1 + n2 + n3 + n4 + n5 + n6?

The first compound represented by Formula 1 is particularly advantageous in terms of performance in that it has at least one kink structure centered on an arylene group and / or a heteroarylene group.

For example, the first compound may be represented by the following formula (I-I) or (II-II). The following formulas are intended to be illustrative and not limiting.

[Chemical Formula 1-I] [Chemical Formula 1-II]

In the above general formulas (I-1) and (II-II), Z, R ¹ to R ⁶ , L ¹ to L ⁶ , and n ¹ to n ⁶ are as defined above.

The bending structure refers to a structure in which two connecting portions of an arylene group and / or a heteroarylene group do not form a straight line structure. For example, in the case of phenylene, o-phenylene and m-phenylene, in which the connecting portions do not have a linear structure, have the bending structure and the connecting portions have a linear structure, phenylene does not have the bending structure.

L ¹ to L ⁶ of the first compound are specifically a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group , A substituted or unsubstituted naphthalenyl group, and the like, and may be, for example, one of the linking groups listed below.

The first compound may be represented by at least one of the following general formulas (1) - (III-1), but is not limited thereto.

[Chemical Formula 1-III] [Chemical Formula 1-IV]

[Chemical Formula 1-V] [Chemical Formula 1-VI]

[Chemical Formula 1-VII]

[Chemical Formula 1-VIII] [Chemical Formula I-IX]

In the above general formulas (I-III) to (I-IX)

Z is as described above,

W is each independently N, C or CR ^b ,

R ^5a to R ^5d are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or combinations thereof .

R ^5a to R ^5d are specifically hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthalene A substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinolinyl group, Substituted phenanthroline, substituted or unsubstituted quinazoline, and may be selected from, for example, a substituted or unsubstituted group listed in Group 1 below.

[Group 1]

In the group 1, * is a connection point,

Wherein "at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, halogen, C1 to C20 alkyl groups, C3 to C20 cycloalkyl groups, C1 to C20 alkoxy groups, C3 to C20 cycloalkoxy groups, C1 to C20 alkylthio groups, An alkyl group, a C6 to C30 aryl group, a C6 to C30 aryloxy group, a C6 to C30 arylthio group, a C2 to C30 heteroaryl group, a C2 to C30 amino group, a C3 to C30 silyl group, a cyano group, a nitro group, Substituted with a carboxyl group.

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

[Group 2]

[A-1] [A-2] [A-3]

[A-4] [A-5] [A-6]

[A-7] [A-8] [A-9]

[A-10] [A-11] [A-12]

[A-13] [A-14] [A-15]

[A-16] [A-17] [A-18]

[A-19] [A-20] [A-21]

[A-22] [A-23] [A-24]

[A-25] [A-26] [A-27]

[A-28] [A-29] [A-30]

[A-31] [A-32] [A-33]

[A-34] [A-35] [A-36]

[A-37] [A-38] [A-39]

[A-40] [A-41] [A-42]

[A-43] [A-44] [A-45]

[A-46] [A-47] [A-48]

[A-49] [A-50] [A-51]

[A-52] [A-53] [A-54]

[A-55] [A-56] [A-57]

[A-58] [A-59] [A-60]

[A-61] [A-62] [A-63]

[A-64] [A-65] [A-66]

[A-67] [A-68] [A-69]

[A-70] [A-71]

[A-72] [A-73]

[A-74] [A-75] [A-76]

[A-77] [A-78] [A-79]

[A-80] [A-81] [A-82]

[A-83] [A-84] [A-85]

[A-86] [A-87] [A-88]

[B-1] [B-2] [B-3]

[B-4] [B-5] [B-6]

[B-7] [B-8] [B-9]

[B-10] [B-11] [B-12]

[B-13] [B-14] [B-15]

[B-16] [B-17] [B-18]

[B-19] [B-20] [B-21]

[B-22] [B-23] [B-24]

[B-25] [B-26] [B-27]

[B-28] [B-29] [B-30]

[B-31] [B-32] [B-33]

[B-34] [B-35] [B-36]

[B-37] [B-38]

[B-39] [B-40]

[B-41] [B-42]

[B-43] [B-44]

[B-45] [B-46]

[B-47] [B-48]

[B-49] [B-50]

[B-51] [B-52] [B-53]

[B-54] [B-55]

[B-56] [B-57] [B-58]

[B-59] [B-60]

[C-1] [C-2] [C-3]

[C-4] [C-5]

The electron transporting auxiliary layer may include the first compound alone or may further include at least one third compound represented by the following general formula (3), which has a relatively high hole property, in addition to the first compound.

(3)

In Formula 3,

L ¹⁰ to L ¹² each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹⁰ to R ¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or combinations thereof .

The compound represented by Formula 3 is a compound having a relatively strong hole characteristic and is contained in the electron transporting auxiliary layer to control the electron injection amount of the first compound and to accumulate holes at the interface between the emitting layer and the electron transporting auxiliary layer The stability of the device can be improved, and the luminous efficiency and lifetime characteristics of the organic optoelectronic device can be remarkably improved.

Ar ³ and Ar ⁴ of the third compound are substituents having a hole or electron characteristic, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl 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 triphenylene group, a substituted or unsubstituted di A benzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

The third compound may be represented by any one of the following formulas (III-1) to (III-III) according to the characteristics of Ar ³ and Ar ⁴ .

[Formula 3-I] [Formula 3-II]

[Formula 3-III]

In the general formulas (III-1) to (III-III), L ¹⁰ to L ¹² and R ¹⁰ to R ¹³ are as defined above,

ET, ET1, and ET2 are each independently a substituent having electron characteristics, and HT, HT1 and HT2 are substituents independently of each other. Substituents "ET "," ET1 ", and "ET2" having electron characteristics of Ar ³ and Ar ⁴ of the second compound may be, for example,

(A)

In the above formula (A)

Each Z is independently N or CR ^q ,

A1 and A2, and ^Rq are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,

Wherein at least one of Z, Al and A2 comprises N,

a and b are each independently 0 or 1;

The substituent represented by the above formula (A) may be one of the functional groups listed in the following group 3, for example.

[Group 3]

,

,

Further, the third compound, Ar ³ And the substituents "HT "," HT1 "and" HT2 "having a hole property in the Ar ⁴ may be one of the functional groups listed in the following Group 4, for example.

[Group 4]

The compound represented by Formula 2 is a compound having a relatively strong hole property and can be included in the electron transporting auxiliary layer together with the first compound to control the electron injection amount of the first compound, It is possible to prevent the accumulation of holes at the interface of the layer to improve the stability of the device. Therefore, the luminous efficiency and lifetime characteristics of the organic optoelectronic device can be remarkably improved.

The third compound may be selected from compounds listed in the following Group 5, but is not limited thereto.

[Group 5]

[D-1] [D-2] [D-3] [D-4]

[D-5] [D-6] [D-7] [D-8]

[D-9] [D-10] [D-11] [D-12]

[D-13] [D-14] [D-15] [D-16]

[D-18] [D-19] [D-20] [D-21]

[D-23] [D-24] [D-25] [D-26]

 [D-28] [D-29] [D-30] [D-31]

[D-33] [D-34] [D-35] [D-36]

[D-38] [D-39] [D-40] [D-41]

[D-43] [D-44] [D-45] [D-46]

[D-48] [D-49] [D-50] [D-51]

[D-53] [D-54] [D-55] [D-56]

[D-58] [D-59] [D-60] [D-61]

[D-63] [D-64] [D-65] [D-66]

[D-68] [D-69] [D-70] [D-71]

[D-73] [D-74] [D-75] [D-76]

.

.

One or more of the third compounds may be used.

The electron transporting layer comprising the first compound having a strong electron characteristic according to an embodiment of the present invention may further include a third compound having a strong hole characteristic.

By using at least one first compound represented by Formula 1 and at least one third compound represented by Formula 3 together, the efficiency and lifetime of the device can be improved.

Specifically, at least one of the first compounds represented by the formulas (1) to (X) and the third compound represented by the formulas (III-1) to (III-III) may be used together.

For example, at least one of the first compounds represented by the formulas (1) - (IV) and (1-VII) may be used together with the third compound represented by the formula (3-1).

In the electron transporting auxiliary layer 35, the first compound and the third compound may be contained at a weight ratio of, for example, about 1:99 to 99: 1. Specifically, it can be included at a weight ratio of 10:90 to 90:10, 20:80 to 80:20, 30:70 to 70:30, and 40:60 to 60:40, 50:50. The first compound and the third compound are mixed at a weight ratio of 1: 2, 1: 3, 1: 4, 1: 5, 1: 1, 2: 1, 3: 1, 4: ≪ / RTI > In the mixing method, the two materials may be mixed beforehand or the respective compounds may be simultaneously deposited at the respective weight ratios.

The electron injecting ability can be controlled according to the ratio of the two compounds by being included in the above range, so that electrons can be prevented from accumulating at the interface of the emitting layer by balancing with the electron transporting ability of the emitting layer.

Further, the holes and / or excitons passing from the light emitting layer are converted into excitons having an energy lower than the energy of the excitons of the light emitting layer due to the electron transporting auxiliary layer 35, so that the influence of the excitons of the holes and / or the light emitting layer on the electron transporting layer 34 Can be minimized. Therefore, when the first compound having relatively high electron characteristics and the third compound having relatively high hole characteristics are used together in the electron transporting layer, the efficiency and lifetime of the device can be improved.

The hole transporting auxiliary layer 33 includes a second compound having a good hole transporting property and reduces the HOMO energy level difference between the hole transporting layer 31 and the light emitting layer 32 to control the injection characteristics of the hole, It is possible to reduce the accumulation of holes at the interface between the light emitting layer 33 and the light emitting layer 32, thereby reducing the quenching phenomenon in which the excitons by the polaron disappear at the interface. As a result, the deterioration phenomenon of the device is reduced and the device is stabilized, thereby improving the efficiency and lifetime.

The second compound may be a compound represented by the following general formula (2).

(2)

In Formula 2,

X < ¹ > is O or S,

R ⁷ to R ⁹ each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 C30 aryloxy groups, substituted or unsubstituted C6 to C30 arylthio groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C2 to C30 amino groups, substituted or unsubstituted C3 to C30 silyl groups , A cyano group, a nitro group, a hydroxyl group or a carboxyl group, or a combination thereof,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,

n7 to n9 each independently represent an integer of 0 to 3;

The second compound may be represented by, for example, the following formula (II-1) or (II-II) depending on the bonding position of the amine substituent.

[Chemical Formula 2-I] [Chemical Formula 2-II]

X ¹ , R ⁷ to R ⁹ , Ar ¹ , Ar ² , L ⁷ to L ⁹ , and n ⁷ to n ⁹ have the same meanings as defined above in the general formulas (II-1) and (II-

L ⁷ to L ⁹ of the second compound are specifically a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group , A substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienylene group and the like,

For example, the second compound may be at least one of the following formulas (II-III) to (II-XI).

[Chemical Formula 2-III] [Chemical Formula 2-IV] Chemical Formula 2-V]

[Chemical Formula 2-VI] [Chemical Formula 2-VII] [Chemical Formula 2-VIII]

[Chemical Formula 2-IX] [Chemical Formula 2-X]

[Chemical Formula 2-XI]

X ¹ , R ⁷ to R ⁹ , Ar ¹ and Ar ² , L ⁷ to L ⁹ , and n ⁷ to n ⁹ in the general formulas 2 to ³ to ² to ⁸ are as described above,

X ² is O, S, or CR ⁱ R ^j ,

X ³ are each independently O or S,

Each of R ^c to R ^j is independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 C30 aryloxy groups, substituted or unsubstituted C6 to C30 arylthio groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C2 to C30 amino groups, substituted or unsubstituted C3 to C30 silyl groups , A cyano group, a nitro group, a hydroxyl group or a carboxyl group, or a combination thereof.

Ar ¹ and Ar ² specifically represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, Substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups , Or a combination thereof,

More specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl A substituted or unsubstituted phenanthrene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

For example, one of the functional groups listed in Group 6 below.

[Group 6]

In the above group 6,

Y is O, S, CR ^l R ^m, R ⁿ SiR ^{o p} or NR ego,

* Is a connection point,

R ^k to R ^p each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aralkyl group, A substituted or unsubstituted C 2 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 2 to C 30 amino group, a substituted or unsubstituted C 3 to C 30 silyl group,

The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do.

The second compound may be selected from, for example, compounds listed in the following Group 7, but is not limited thereto.

[Group 7]

[E-1] [E-2] [E-3]

[E-6] [E-7] [E-8]

[E-11] [E-12] [E-13]

[E-16] [E-17] [E-18] [E-19]

 [E-21] [E-22] [E-23] [E-24]

[E-26] [E-27] [E-28] [E-29]

[E-31] [E-32] [E-33] [E-34]

[E-36] [E-37] [E-38] [E-39]

[E-41] [E-42] [E-43] [E-44]

[E-46] [E-47] [E-48] [E-49]

[E-50] [E-51] [E-52] [E-53]

[E-55] [E-56] [E-57]

[E-60] [E-61] [E-62] [E-63]

[E-65] [E-66] [E-67]

[E-68] [E-69] [E-70] [E-71]

[E-72] [E-73] [E-74] [E-75]

[E-77] [E-78] [E-79] [E-80]

[E-81] [E-82] [E-83] [E-84]

[E-85] [E-86] [E-87] [E-88]

[F-1] [F-2] [F-3] [F-4]

[F-6] [F-7] [F-8] [F-9]

[F-10] [F-11] [F-12] [F-13]

[F-14] [F-15] [F-16] [F-17] [F-18]

[F-19] [F-20] [F-21] [F-22]

[F-24] [F-25] [F-26] [F-27]

[F-28] [F-29] [F-30] [F-31] [F-32]

[F-33] [F-34] [F-35] [F-36]

[F-38] [F-39] [F-40] [F-41]

[F-42] [F-43] [F-44] [F-45]

[F-47] [F-48] [F-49] [F-50]

[G-1] [G-2] [G-3] [G-4]

[G-5] [G-6] [G-7] [G-8]

[G-9] [G-10] [G-11] [G-12] [G-13]

[G-14] [G-15] [G-16] [G-17] [G-18]

[G-19] [G-20] [G-21] [G-22]

[G-23] [G-24] [G-25] [G-26]

[G-27] [G-28] [G-29] [G-30]

[H-1] [H-2] [H-3] [H-4] [H-

[H-6] [H-7] [H-8] [H-9]

[H-11] [H-12] [H-13] [H-14]

[H-16] [H-17] [H-18] [H-19] [H-20]

[H-21] [H-22] [H-23] [H-24]

[H-26] [H-27] [H-28] [H-29]

[H-31] [H-32] [H-33] [H-34]

[H-36] [H-37] [H-38] [H-39]

[H-41] [H-42] [H-43] [H-44]

[H-46] [H-47] [H-48] [H-49]

[H-51] [H-52] [H-53] [H-54]

[H-56] [H-57] [H-58] [H-59]

[H-61] [H-62] [H-63] [H-64]

[H-66] [H-67] [H-68] [H-69]

[H-71] [H-72] [H-73] [H-74]

[H-76] [H-77] [H-78] [H-79]

[H-81] [H-82] [H-83] [H-84]

[H-86] [H-87] [H-88] [H-89]

[H-91] [H-92] [H-93] [H-94]

[H-96] [H-97] [H-98]

.

.

The organic optoelectronic device according to an embodiment of the present invention includes a ring containing at least one nitrogen to provide a structure capable of receiving electrons upon application of an electric field, An auxiliary layer or an electron transporting auxiliary layer simultaneously containing a first compound having a strong electron characteristic and a third compound having a strong hole characteristic,

A hole transporting auxiliary layer including a second compound having a good hole transporting property capable of controlling injection characteristics of holes by reducing the HOMO energy level difference between the hole transporting layer 31 and the light emitting layer 32 can be included at the same time.

By using these materials together, it is possible to improve the efficiency by adjusting the charge balance through the hole injection control ability of the hole transporting auxiliary layer and the electron injection controlling ability of the electron transporting auxiliary layer, and the hole transporting auxiliary layer and the electron transporting auxiliary layer Charge accumulation at each interface of the organic layer is prevented, deterioration of the device is reduced, the device is stabilized, and the lifetime can be improved.

Specifically, the electron transporting auxiliary layer is a compound selected from the first compound represented by the above Chemical Formulas 1-III to 1-X, specifically the first compound represented by Chemical Formulas 1-IV and 1-VII , ≪ / RTI >

May further contain a compound selected from the third compound represented by the above general formulas (III-1) to (III-III).

The hole transporting auxiliary layer is a compound selected from the second compounds represented by the above formulas 2-III to 2-XI, specifically, the compounds represented by the following formulas 2-VII, 2-VIII, 2-X, ≪ / RTI > or a pharmaceutically acceptable salt thereof.

For example, the electron transporting auxiliary layer may include a compound selected from the first compound represented by the above Chemical Formulas 1-IV and 1-VII and a third compound represented by the above Chemical Formula 3-III,

The electron transporting auxiliary layer and the hole transporting auxiliary layer may be formed by reacting a compound selected from the first compound represented by the above Chemical Formulas 1-IV and 1-VII and a compound selected from the above Chemical Formulas 2-VII, 2-VIII, 2-X, 2-XI, or the electron transporting auxiliary layer may further comprise a third compound.

The hole transporting auxiliary layer 33 and the electron transporting auxiliary layer 35 can be applied on the hole transporting layer in a thickness of 0.1 nm to 20.0 nm by a vapor deposition or inkjet process, nm to 2 nm, a thickness of 0.4 nm to 1.0 nm, and the like.

The organic layer 30 may optionally include a hole injection layer 37 located between the anode 10 and the hole transport layer 31 and / or an electron injection layer 36 located between the cathode 20 and the electron transport layer 34. [ As shown in FIG.

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

In the present invention, the organic optoelectronic device may be selected from the group consisting of an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photoconductor drum, and an organic memory device.

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 first compound

Synthetic example  1: Synthesis of intermediate I-1

[Reaction Scheme 1]

The compound 2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 187 mmol, purchased from TCI) was dissolved in 1 L of THF in a nitrogen atmosphere, and then 3-bromophenyl boronic (45 g, 224.12 mmol, TCI) and tetrakis (triphenylphosphine) palladium (2.1 g, 1.87 mmol) were added and stirred. Saturated water-saturated potassium carbonate (64 g, 467 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), and then dried over anhydrous MgSO 4. The extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by column chromatography to obtain the above compound I-1 (69 g, 95%).

HRMS (70 eV, EI +): m / z calcd for C21H14BrN3: 387.0371, found: 387

Elemental Analysis: C, 65%; H, 4%

Synthetic example  2: Synthesis of intermediate I-2

[Reaction Scheme 2]

Intermediate I-1 and 3-chlorophenyl boronic acid (TCI) were synthesized and purified in the same manner as in the synthesis of Intermediate I-1 to obtain 51 g (95%) of Intermediate I-2.

HRMS (70 eV, EI +): m / z calcd for C27H18ClN3: 419.1189, found: 419

Elemental Analysis: C, 77%; H, 4%

Synthetic example  3: Synthesis of Intermediate I-3

[Reaction Scheme 3]

Bis (pinacolato) diboron (72.5 g, 285 mmol, Aldrich) and 1,1'-bis (diphenylphosphine) were dissolved in 1 L of dimethylforamide (DMF) ferrocene dichloropalladium (II) (2 g, 2.38 mmol) and potassium acetate (58 g, 595 mmol) were added and heated at 150 ° C for 48 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by column chromatography to obtain the above compound I-3 (107 g, 88%).

HRMS (70 eV, EI +): m / z calcd for C33H30BN3O2: 511.2431, found: 511

Elemental Analysis: C, 77%; H, 6%

Synthetic example  4: Synthesis of intermediate I-4

[Reaction Scheme 4]

The compound I-3 (50 g, 98 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and 1-bromo-3-iodobenzene (33 g, 117 mmol, Aldrich) and tetrakis (triphenylphosphine) palladium , 0.98 mmol) were added and stirred. Saturated water-saturated potassium carbonate (34 g, 245 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO 4, followed by filtration and concentration under reduced pressure. The thus-obtained residue was separated and purified by column chromatography to obtain the above compound I-4 (50 g, 95%).

HRMS (70 eV, EI +): m / z calcd for C30H27BO2: 539.0997, found: 539

Elemental Analysis: C, 73.34; H, 4.10

Synthetic example  5: Synthesis of intermediate I-5

[Reaction Scheme 5]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-3 to obtain 95 g (88%) of Intermediate I-5.

HRMS (70 eV, EI +): m / z calcd for C39H34BN3O2: 587.2744, found: 587

Elemental Analysis: C, 80%; H, 6%

Synthetic example  6: Synthesis of Intermediate I-10

[Reaction Scheme 6]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-4 to obtain 50 g (95%) of Intermediate I-10.

HRMS (70 eV, EI +): m / z calcd for C30H27BO2: 539.0997, found: 539

Elemental Analysis: C, 73.34; H, 4.10

Synthetic example  7: Synthesis of Intermediate I-11

[Reaction Scheme 7]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-3 to obtain 95 g (88%) of Intermediate I-11.

HRMS (70 eV, EI +): m / z calcd for C39H34BN3O2: 587.2744, found: 587

Elemental Analysis: C, 80%; H, 6%

Synthetic example  8: Synthesis of Intermediate I-27

[Reaction Scheme 8]

Synthesis and purification were carried out in the same manner as in the synthesis of Intermediate I-4 to obtain 50 g (95%) of Intermediate I-27.

HRMS (70 eV, EI +): m / z calcd for C39H26BrN3: 615.1310, found 616

Elemental Analysis: C, 76%; H, 4%

Synthetic example  9: Synthesis of intermediate I-28

[Reaction Scheme 9]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-3 to obtain 86 g (80%) of Intermediate I-28.

HRMS (70 eV, EI +): m / z calcd for C45H38BN3O2: 663.3057, found: 663

Elemental Analysis: C, 81%; H, 6%

Synthetic example  10: Synthesis of Intermediate I-37

[Reaction Scheme 10]

Synthesis and purification were carried out in the same manner as in the synthesis of Intermediate I-3 to obtain 100 g (89%) of Intermediate I-37.

Synthetic example  11: Synthesis of Intermediate I-38

[Reaction Scheme 11]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-4 to obtain 54 g (73%) of Intermediate I-38.

Synthetic example  12 to 16: Synthesis of intermediate with pyridine core

[Reaction Scheme 12]

[Reaction Scheme 13]

[Reaction Scheme 14]

[Reaction Scheme 15]

[Reaction Scheme 16]

Intermediate I-1 to Intermediate I-5, Intermediate I-5, except that 4-chloro-2,6-diphenylpyridine (TCI) was used instead of 2-chloro-4,6-diphenyl- Synthesis and purification were conducted in the same manner as in the synthesis method of Intermediate I-10 and Intermediate I-11 to obtain Intermediate I-12 to Intermediate I-16.

Synthetic example  17 to 21: Synthesis of intermediate with pyrimidine core

[Reaction Scheme 17]

[Reaction Scheme 18]

[Reaction Scheme 19]

[Reaction Scheme 20]

[Reaction Scheme 21]

Intermediates I-1 to I (except for using 2-chloro-4,6-diphenyl-1,3-pyrimidine (TCI) instead of 2-chloro-4,6- Synthesis and purification were carried out in the same manner as in the synthesis of Intermediate I-5, Intermediate I-10 and Intermediate I-11, to give Intermediate I-17 to Intermediate I-21.

Synthetic example  22 to 26: Phenylene  Synthesis of intermediates with core

[Reaction Scheme 22]

[Reaction Scheme 23]

[Reaction Scheme 24]

[Reaction Scheme 25]

[Reaction Scheme 26]

(5-bromo-1,3-phenylene) dipyridine (JP2008-127326A, see Example 1 of CHEMIPROKASEI KAISHA) instead of 2-chloro-4,6-diphenyl-1,3,5- Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-1 to Intermediate I-5, Intermediate I-10 and Intermediate I-11, except that Intermediate I-22 to Intermediate I-26 were obtained.

Synthetic example  27: Synthesis of Intermediate I-39

[Reaction Scheme 27]

Synthesis and purification were carried out in the same manner as in the synthesis of intermediate I-4 to obtain 35 g (57%) of intermediate I-39.

Synthetic example  28: Synthesis of Intermediate I-40

[Reaction Scheme 28]

Synthesis and purification were carried out in the same manner as in the synthesis of intermediate I-4 to obtain 44 g (99%) of intermediate I-40.

Synthetic example  29: Synthesis of Intermediate I-41

[Reaction Scheme 29]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-3 to obtain 42 g (72%) of Intermediate I-41.

Synthetic example  30: Intermediate L- 1 of  synthesis

[Reaction Scheme 30]

30 g (162.68 mmol, Aldrich) of 2,4,6-trichloro-1,3,5-triazine is dissolved in 325 ml of tetrahydrofuran solvent in a 500 ml flask. Cool the solvent using ice water and slowly drop 54.23 ml (162.68 mmol) of 3M-concentration phenylmagnesium bromide in a nitrogen stream using a dropping funnel. Phenylmagnesium bromide is added and stirred for 30 minutes, then water is added to terminate the reaction. Tetrahydrofuran and water are separated to remove water, and then tetrahydrofuran is removed through a distiller to obtain a solid. The solid is stirred with 100 ml of methanol and then filtered. The solid was again stirred with 100 ml of hexane and then filtered to obtain Intermediate L-1 (27 g, 73% yield).

calcd. C9H5Cl2N3: C, 47.82; H, 2.23; Cl, 31.37; N, 18.59;

found: C, 47.56; H, 2.12; Cl, 31.42; N, 18.43

Synthetic example  31 to 32: Intermediate L-7, and Intermediate L- 8 of  synthesis

Intermediates L-7 and L-8 shown as more specific examples of the compound of the present invention were synthesized in the same manner as the synthesis method of intermediates I-39, I-40 and I-41 according to Synthesis Examples 27-29. (Using three basic reactions: Suzuki reaction, Br bore reaction, Cl bore reaction)

[Reaction Scheme 31]

[Reaction Scheme 32]

Synthetic example  33: Synthesis of Compound A-1

[Reaction Scheme 33]

Bromo-1,1'-biphenyl (9.5 g, 40 mmol) and tetrakis (triphenylphosphine) were dissolved in 0.2 L of tetrahydrofuran (THF) in a nitrogen atmosphere, palladium (0.39 g, 0.34 mmol) were added and stirred. Potassium hydroxide (12 g, 85 mmol) saturated with water was added and the mixture was refluxed by heating at 80 ° C for 20 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO 4, followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by column chromatography to obtain the above compound A-1 (24 g, 70%).

HRMS (70 eV, EI +): m / z calcd for C45H31N3: 613.2518, found: 613

Elemental Analysis: C, 88%; H, 5%

Synthetic example  34 to 39: Synthesis of Compound

Synthesis of second compound

Synthetic example  40: Synthesis of intermediate M-1

[Reaction Scheme 34]

Synthesis and purification were conducted in the same manner as in the synthesis of intermediate I-4 to obtain 27 g (89%) of intermediate M-1.

LC-Mass (theory: 322.00 g / mol, measured: M + = 322.09 g / mol, M + 2 = 324.04 g / mol)

Synthetic example  41: Synthesis of intermediate M-2

[Reaction Scheme 35]

Synthesis and purification were carried out in the same manner as in the synthesis of intermediate I-4 to obtain 29 g (91%) of intermediate M-2.

LC-Mass (theoretical value: 337.98 g / mol, measured: M + = 338.04 g / mol, M + 2 = 340.11 g / mol)

Synthetic example  42: Synthesis of intermediate M-3

[Reaction Scheme 36]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate I-2 to obtain 23.9 g (91%) of Intermediate M-3.

LC-Mass (theoretical value: 278.05 g / mol, measured: M + = 278.12 g / mol, M + 2 = 280.13 g / mol)

Synthetic example  43: Synthesis of intermediate M-4

[Reaction Scheme 37]

Synthesis and purification were carried out in the same manner as in the synthesis of Intermediate I-2 to obtain 25.6 g (92%) of Intermediate M-4.

LC-Mass (294.03 g / mol, M + = 294.16 g / mol, M + 2 = 296.13 g / mol)

Synthetic example  44: Synthesis of intermediate M-5

[Reaction Scheme 38]

10 g (30.9 mmol) of intermediate M-1, 6.3 g (37.08 mmol) of 4-aminobiphenyl and 5.35 g (55.6 mmol) of sodium di-t-butoxide were added to a round bottom flask and 155 ml of toluene was added to dissolve. 0.178 g (0.31 mmol) of Pd (dba) 2 and 0.125 g (0.62 mmol) of tri-tertiary-butylphosphine were added in this order, followed by stirring under reflux for 4 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and distilled water. The organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (7: 3 by volume) to obtain 9.92 g (78%) of Intermediate M-5 as a target compound.

LC-Mass (theory: 411.16 g / mol, measured: M + = 411.21 g / mol)

Synthetic example  45: Synthesis of intermediate M-6

[Reaction Scheme 39]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate M-5 to obtain 11 g (76%) of Intermediate M-6.

LC-Mass (theory: 467.17 g / mol, measured: M + = 467.23 g / mol)

Synthetic example  46: Synthesis of intermediate M-7

[Reaction Scheme 40]

Synthesis and purification were carried out in the same manner as in the synthesis of Intermediate M-5 to obtain 10.6 g (80%) of Intermediate M-7.

LC-Mass (theory: 427.14 g / mol, measured: M + = 427.19 g / mol)

Synthetic example  47: Synthesis of intermediate M-8

[Reaction Scheme 41]

Synthesis and purification were conducted in the same manner as in the synthesis of Intermediate M-5 to obtain 10.5 g (80%) of Intermediate M-8.

LC-Mass (theory: 427.14 g / mol, measured: M + = 427.20 g / mol)

Synthetic example  48: Synthesis of intermediate M-9

[Reaction Scheme 42]

(94.3 mmol) of 4-dibenzofuranboronic acid and 16.2 g (94.3 mmol) of 4-bromoaniline were added to a round-bottomed flask, and toluene (300 ml) was added to dissolve the solution. To the solution, 19.5 g (141.5 mmol) 117 ml were added and stirred. 1.09 g (0.94 mmol) of tetrakistriphenylphosphine palladium was added thereto, and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (9: 1 by volume) to give 17.4 g (71% yield) of intermediate compound M-9 as a white solid.

LC-Mass (theory: 259.1 g / mol, measured: M + = 259.21 g / mol)

Synthetic example  49: Synthesis of intermediate M-10

[Reaction Scheme 43]

10 g (30.9 mmol) of intermediate M-1, 9.6 g (37.08 mmol) of intermediate M-9 and 5.35 g (55.6 mmol) of sodium di-t-butoxide were added to a round bottom flask and 155 ml of toluene was added to dissolve. 0.178 g (0.31 mmol) of Pd (dba) 2 and 0.125 g (0.62 mmol) of tri-tertiary-butylphosphine were added in this order, and the mixture was stirred under reflux for 4 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water, and the organic layer was dried with magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (7: 3 by volume) to give 11.2 g (yield 72%) of intermediate compound M-10 as a white solid.

LC-Mass (theoretical value: 501.17 g / mol, measured: M + = 501.31 g / mol)

Synthetic example  50: Synthesis of Compound H-1

[Reaction Scheme 44]

15 g (46.4 mmol) of intermediate M-1, 3.9 g (23.2 mmol) of 4-aminobiphenyl and 6.7 g (69.6 mmol) of sodium di-t-butoxide were added to a round bottom flask and 155 ml of toluene was added to dissolve. 0.53 g (0.928 mmol) of Pd (dba) 2 and 0.38 g (1.86 mmol) of tri-tertiary-butylphosphine were added in this order, followed by stirring under reflux for 4 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water, and the organic layer was dried with magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (8: 2 by volume) to obtain 13.7 g (90%) of the target compound H-1.

LC-Mass (theory: 653.24 g / mol, measured: M + = 653.31 g / mol)

Synthetic example  51 to 62: Synthesis of Compound

Synthesis of the third compound

Synthetic example  63: Synthesis of Compound D-1

[Reaction Scheme 45]

Step 1: Synthesis of intermediate (A)

After 140.4 g (674 mmol) of 2-benzalacetophenone, 199.04 g (808.77 mmol) of pyridine salt compound and 415.6 g (5391 mmol) of ammonium acetate were suspended in methanol (1720 ml), the mixture was refluxed at 110 ° C for 2 hours. After the reaction, the product was precipitated in distilled water to form a solid, and the resulting solid was filtered to obtain 106 g (64%) of intermediate (A).

Step 2: Synthesis of intermediate (B)

100 g (405.67 mmol) of intermediate (A), 172.74 g (1217 mmol) of P ₂ O ₅ and 196.17 g (608.5 mmol) of Tetra-n-butylammonium bromide were all added thereto and suspended in chlorobenzene. Lt; 0 > C for 14 hours. After the reaction, the solvent was removed, and the organic layer extracted with dichloromethane and distilled water was filtered to remove 150 ml of the obtained organic layer. Methanol was then poured to form a precipitate, and the resulting solid matter was filtered to obtain 89 g of 71 %).

Step 3: Synthesis of Compound J

The starting material, phenyl-9H-carbazol-3-yl boronic acid and 3-bromocarbazole were purchased from TCI to give the compound A-1 Synthesis was carried out in the same manner as in Synthesis. After the completion of the reaction, the reactants are poured into methanol to remove solids, and then the solids are dissolved again in chlorobenzene. Activated carbon and anhydrous magnesium sulfate are added and stirred. The solution was filtered and then recrystallized from chlorobenzene and methanol to obtain 22.6 g (68%) of Compound J.

HRMS (70 eV, EI +): m / z calcd for C30 H20 N2: 408.16, found: 408

Elemental Analysis: C, 88%; H, 5%

Step 4: Synthesis of Compound D-1

22.42 g (54.88 mmol) of the compound represented by the compound J, 20.43 g (65.85 mmol) of the 2-bromo-4,6-diphenylpyridine obtained in the second step (intermediate (B)) and tert- After dissolving 7.92 g (82.32 mmol) of toluene in 400 ml of toluene, 1.65 g (1.65 mmol) of palladium dibenzylideneamine and 1.78 g (4.39 mmol) of tertiary butyl are added dropwise. The reaction solution was heated at 110 DEG C for 12 hours under a stream of nitrogen and stirred. After completion of the reaction, methanol is poured into the reaction product to filter out the resulting solids, and the solids are again dissolved in chlorobenzene, and activated carbon and anhydrous magnesium sulfate are added thereto and stirred. The solution was filtered and then recrystallized using chlorobenzene and methanol to obtain 28.10 g (80%) of the compound D-1.

HRMS (70 eV, EI +): m / z calcd for C 47 H 31 N 3: 637.25, found: 637

Elemental Analysis: C, 89%; H, 5%

Synthetic example  64: Synthesis of compound D-23

[Reaction Scheme 46]

Step 1: Synthesis of intermediate (K)

20 g (90%) of the intermediate (K) was obtained in the same manner as in the synthesis of the compound D-1.

Step 2: Synthesis of intermediate (L)

20 g (62.6 mmol) of the intermediate (K) was suspended in DMF (200 ml), 12.93 g (72.67 mmol) of NBS was added in small portions, and the mixture was refluxed for 12 hours. After adding distilled water and terminating the reaction, the organic layer obtained by extraction with dichloromethane is subjected to silica gel filtration. Subsequently, the organic solution was removed, and silica gel column chromatography was performed using hexane: dichloromethane = 7: 3 (v / v). The resulting solid was recrystallized from dichloromethane and n-hexane to obtain 22.4 g (90%) of intermediate (L).

Step 3: Synthesis of intermediate (N)

In the same manner as in the synthesis of Intermediate I-3, 22.5 g (90%) of Intermediate (N) was obtained by purification.

Step 4: Synthesis of compound D-23

10 g (34.83 mmol) of intermediate (N), 9- [1,1'-biphenyl-4-yl] -3-bromo-9H- (0.7 mmmol) of tetrakis- (triphenylphosphine) palladium (0) was added to a solution of 11.77 g (38.31 mmol) of potassium carbonate, 14.44 g 140 ml of toluene and 50 ml of distilled water, and the mixture was refluxed and stirred for 12 hours. Subsequently, recrystallization from dichloromethane and n-hexane gave 18.7 g (92%) of the compound D-23.

HRMS (70 eV, EI +): m / z calcd for C48H32N2: 636.26, found: 636

Elemental Analysis: C, 91%; H, 5%

Synthetic example  65: Synthesis of Compound D-71

[Reaction Scheme 47]

The starting material, 3-bromo-9-biphenylcarbazole and 9-phenyl-9H-carbazol-3-yl boronic acid, Was obtained from TCI and synthesized in the same manner as in the synthesis of Compound A-1, and recrystallized from dichloromethane and n-hexane to obtain 13.8 g (92%) of Compound D-71.

HRMS (70 eV, EI +): m / z calcd for C36H24N2: 484.19, found: 484

Elemental Analysis: C, 89%; H, 5%

Synthetic example  66: Synthesis of Compound D-72

[Reaction Scheme 48]

The starting material 3-phenyl-3-bromo-9-biphenylcarbazole was synthesized in the same manner as in Structure 56D of WO2010-041872 and phenyl-9H-carbazole-3 9-phenyl-9H-carbazol-3-yl boronic acid was purchased from TCI and synthesized in the same manner as in the synthesis of Compound A-1, and recrystallized from dichloromethane and n-hexane to obtain Compound D -72 < / RTI > 18 g (89%).

Fabrication of organic light emitting device

Example  One

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum deposition machine. N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'- Diamine (Compound A) was vacuum-deposited to form a hole injection hole having a thickness of 700 Å. The hole injection layer was formed by vacuum deposition of N4, N4'-diphenyl-N4 and N4'-bis (9- Layer was formed on the hole injection layer and 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT- CN) (Compound B) was deposited to a thickness of 50 ANGSTROM and then N- (biphenyl-4-yl) -9,9-dimethyl-N- (4- Phenyl) -9H-fluorene-2-amine (N- (4-fluorophenyl) -9H-carbazol- 9H-fluoren-2-amine (Compound C) was deposited to a thickness of 700 Å to form a hole transport layer. A hole transporting auxiliary layer having a thickness of 50 Å was formed on the hole transporting layer by vacuum evaporation of the compound H-96 obtained in Synthesis Example 58. Subsequently, BH113 and BD370, which are sold by SFC Co., as a blue fluorescent light emitting host and a dopant, were doped on the hole transporting auxiliary layer to a thickness of 200 Å to form a light emitting layer. Subsequently, Compound A-37 obtained in Synthesis Example 37 was vacuum-deposited on the light-emitting layer to form an electron transporting layer having a thickness of 50 Å.

Subsequently, 8- (4- (4- (naphthalen-2-yl) -6- (naphthalen-3-yl) -1,3,5-triazin-2-yl) phenyl) quinoline 2-yl) phenyl) quinoline (Compound E) and Liq were reacted with 8- (4- (4- (4- (naphthalen- At the same time, an electron transport layer having a thickness of 310 ANGSTROM was formed by vacuum deposition at a ratio of 1: 1, and an anode was formed by sequentially depositing Liq 15 ANGSTROM and Al 1200 ANGSTROM over the electron transport layer to fabricate an organic light emitting device.

The organic light emitting device has a structure having seven organic thin film layers, and specifically,

A hole transporting auxiliary layer H-96 (50 Å) / EML [BH113: BD370 (95: 5 wt%)] (200 Å) / electron transporting auxiliary layer (ITO / A 700 Å / B 50 Å / [A-37 (50 Å) / E: Liq = 1: 1 (310 Å) / Liq (15 Å) / Al (1200 Å).

Example  2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound H-98 obtained in Synthesis Example 56 was used instead of Compound H-96 in the hole transporting assisting layer.

Example  3

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound E-70 obtained in Synthesis Example 55 was used instead of Compound H-96 in the hole transporting assisting layer.

Example  4

An organic light emitting device was fabricated in the same manner as in Example 1 except that a hole transporting layer (Compound C) was deposited to a thickness of 750 A without forming a hole transporting auxiliary layer.

Example  5

The same procedure as in Example 1 was carried out except that the layer A-7 obtained in Synthesis Example 34 and the compound D-72 obtained in Synthesis Example 66 were formed in a thickness of 50 Å by vacuum evaporation at a weight ratio of 6: To prepare an organic light emitting device.

Example  6

Compound H-97 obtained in Synthesis Example 62 was used in place of Compound H-96 in the hole transporting auxiliary layer, Compound A-7 obtained in Synthesis Example 34 and D-72 obtained in Synthesis Example 66 were added to the electron transporting auxiliary layer at a ratio of 6: 4 was formed by vacuum evaporation to form a layer having a thickness of 50 Å. An organic light emitting device was fabricated in the same manner as in Example 1.

Example  7

Compound H-11 obtained in Synthesis Example 52 was used instead of Compound H-96 in the hole transporting auxiliary layer, Compound A-7 obtained in Synthesis Example 34 and D-72 obtained in Synthesis Example 66 were used in the electron transporting auxiliary layer at a ratio of 6: 4 was formed by vacuum evaporation to form a layer having a thickness of 50 Å. An organic light emitting device was fabricated in the same manner as in Example 1.

Example  8

Compound H-11 obtained in Synthesis Example 52 was used in place of Compound H-6 in the hole transporting auxiliary layer, Compound A-7 obtained in Synthesis Example 34 and D-72 obtained in Synthesis Example 66 were added to the electron transporting auxiliary layer at a ratio of 4: 6, a layer having a thickness of 50 Å was formed by vacuum evaporation.

Example  9

Compound H-11 obtained in Synthesis Example 52 was used instead of Compound H-96 in the hole transporting auxiliary layer, Compound A-24 obtained in Synthesis Example 35 and D-71 obtained in Synthesis Example 65 were added to the electron transporting auxiliary layer at a ratio of 1: 1, a layer having a thickness of 50 Å was formed by vacuum evaporation.

Example  10

An organic light emitting device was fabricated in the same manner as in Example 5, except that the hole transport layer (Compound C) was deposited to a thickness of 750 A to form a hole transport layer without forming a hole transporting auxiliary layer.

Example  11

An organic light emitting device was fabricated in the same manner as in Example 8, except that a hole transporting layer (Compound C) was deposited to a thickness of 750 A to form a hole transporting layer without forming a hole transporting auxiliary layer.

Example  12

An organic light emitting device was fabricated in the same manner as in Example 9, except that the hole transport layer (Compound C) was deposited to a thickness of 750 A to form a hole transport layer without forming a hole transporting auxiliary layer.

Comparative Example  One

Instead of forming the hole transporting auxiliary layer, a hole transporting layer (Compound C) was formed by vapor deposition to a thickness of 750 ANGSTROM, and an electron transporting auxiliary layer was not formed. Instead of compound E: Liq = 1: E: Liq = 1: 1 (360 ANGSTROM).

evaluation

Emitting efficiency and roll-off characteristics of the organic luminescent devices according to Examples 1 to 12 and Comparative Example 1 were evaluated.

The specific measurement method is as follows, and the results are shown in Table 2.

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

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (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, 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).

(4) Life measurement

The time at which the luminance (cd / m ²⁾ was maintained at 750 cd / m ² and the current efficiency (cd / A) decreased to 97% was measured and the results were obtained.

Hole transporting auxiliary layer Electron transporting auxiliary layer The driving voltage (V) Luminous efficiency
(cd / A) T97 Life (h) @ 750nit
(%) The first compound The second compound First compound: second compound Example 1 H-96 A-37 - - 4.26 7.2 44 Example 2 H-98 A-37 - - 4.19 7.0 37 Example 3 E-70 A-37 - - 4.24 7.1 25 Example 4 - A-37 - - 4.29 6.1 55 Example 5 H-96 A-7 D-72 6: 4 3.94 8.0 29 Example 6 H-97 A-7 D-72 6: 4 3.91 7.7 32 Example 7 H-11 A-7 D-72 6: 4 3.91 7.9 30 Example 8 H-11 A-7 D-72 4: 6 3.94 7.6 25 Example 9 H-11 A-24 D-71 5: 5 4.09 7.1 45 Example 10 - A-7 D-72 6: 4 3.90 7.3 42 Example 11 A-7 D-72 4: 6 4.05 6.7 39 Example 12 - A-24 D-71 5: 5 4.11 6.6 40 Comparative Example 1 - - - - 4.36 5.9 25

Referring to Table 1, it can be seen that the organic light emitting devices according to Examples 1 to 12 are significantly improved in luminous efficiency and lifetime characteristics compared with the organic light emitting devices according to Comparative Example 1, respectively.

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.

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (20)

The anode and cathode,
A light emitting layer positioned between the anode and the cathode,
An electron transporting layer positioned between the cathode and the light emitting layer, and
An electron transporting auxiliary layer disposed between the electron transporting layer and the light emitting layer,
/ RTI >
Wherein the electron transport assisting layer comprises at least one first compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
R ¹ to R ⁶ , and R ^a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A combination thereof,
L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group or a combination thereof,
n1 to n6 each independently represent an integer of 0 to 5,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. The anode and cathode,
A light emitting layer positioned between the anode and the cathode,
A hole transporting layer disposed between the anode and the light emitting layer,
A hole transporting auxiliary layer positioned between the hole transporting layer and the light emitting layer,
An electron transporting layer positioned between the cathode and the light emitting layer, and
And an electron transporting layer positioned between the electron transporting layer and the light emitting layer,
Wherein the electron transporting layer comprises at least one first compound represented by the following Formula 1,
Wherein the hole transporting auxiliary layer comprises at least one second compound represented by the following formula (2): < EMI ID =
[Chemical Formula 1]

In Formula 1,
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
R ¹ to R ⁶ , and R ^a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A combination thereof,
L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group or a combination thereof,
n1 to n6 each independently represent an integer of 0 to 5,
(2)

In Formula 2,
X < ¹ > is O or S,
R ⁷ to R ⁹ each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 C30 aryloxy groups, substituted or unsubstituted C6 to C30 arylthio groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C2 to C30 amino groups, substituted or unsubstituted C3 to C30 silyl groups , A cyano group, a nitro group, a hydroxyl group or a carboxyl group, or a combination thereof,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,
n7 to n9 each independently represent an integer of 0 to 3,
"Substitution" in the above formulas (1) and (2) means that at least one hydrogen is substituted with a substituent selected from the group consisting of a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, C30 alkyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, C1 to C10 trifluoroalkyl group or cyano group ≪ / RTI > 3. The method according to claim 1 or 2,
Wherein the first compound is represented by the following formula (I-1) or (II-II): < EMI ID =
[Chemical Formula 1-I] [Chemical Formula 1-II]

In the above general formulas (I-1) and (II-II)
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
R ¹ to R ⁶ , and R ^a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A combination thereof,
L ¹ to L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group or a combination thereof,
n1 to n6 each independently represent an integer of 0 to 5,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method according to claim 1 or 2,
Wherein the first compound is represented by at least one of the following formulas (1) - (III-1): < EMI ID =
[Chemical Formula 1-III] [Chemical Formula 1-IV]

[Chemical Formula 1-V] [Chemical Formula 1-VI]

[Chemical Formula 1-VII]

[Chemical Formula 1-VIII] [Chemical Formula I-IX]

In the above general formulas (I-III) to (I-IX)
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
W is each independently N, C or CR ^b ,
R ^5a to R ^5d , R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 hetero An aryl group or a combination thereof,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method according to claim 1 or 2,
Wherein the first compound is at least one of the compounds listed in the following Group 2:
[Group 2]
[A-1] [A-2] [A-3]

[A-4] [A-5] [A-6]

[A-7] [A-8] [A-9]

[A-10] [A-11] [A-12]

[A-13] [A-14] [A-15]

[A-16] [A-17] [A-18]

[A-19] [A-20] [A-21]

[A-22] [A-23] [A-24]

[A-25] [A-26] [A-27]

[A-28] [A-29] [A-30]

[A-31] [A-32] [A-33]

[A-34] [A-35] [A-36]

[A-37] [A-38] [A-39]

[A-40] [A-41] [A-42]

[A-43] [A-44] [A-45]

[A-46] [A-47] [A-48]

[A-49] [A-50] [A-51]

[A-52] [A-53] [A-54]

[A-55] [A-56] [A-57]

[A-58] [A-59] [A-60]

[A-61] [A-62] [A-63]

[A-64] [A-65] [A-66]

[A-67] [A-68] [A-69]

[A-70] [A-71]

[A-72] [A-73]

[A-74] [A-75] [A-76]

[A-77] [A-78] [A-79]

[A-80] [A-81] [A-82]

[A-83] [A-84] [A-85]

[A-86] [A-87] [A-88]

[B-1] [B-2] [B-3]

[B-4] [B-5] [B-6]

[B-7] [B-8] [B-9]

[B-10] [B-11] [B-12]

[B-13] [B-14] [B-15]

[B-16] [B-17] [B-18]

[B-19] [B-20] [B-21]

[B-22] [B-23] [B-24]

[B-25] [B-26] [B-27]

[B-28] [B-29] [B-30]

[B-31] [B-32] [B-33]

[B-34] [B-35] [B-36]

[B-37] [B-38]

[B-39] [B-40]

[B-41] [B-42]

[B-43] [B-44]

[B-45] [B-46]

[B-47] [B-48]

[B-49] [B-50]

[B-51] [B-52] [B-53]

[B-54] [B-55]

[B-56] [B-57] [B-58]

[B-59] [B-60]

[C-1] [C-2] [C-3]

[C-4] [C-5]

. 3. The method according to claim 1 or 2,
Wherein the electron transport assisting layer further comprises at least one third compound represented by the following formula (3): < EMI ID =
(3)

In Formula 3,
L ¹⁰ to L ¹² each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ¹⁰ to R ¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or combinations thereof ,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. The method of claim 6,
Wherein the third compound is represented by at least one of the following general formulas (III-1) to (III-III):
[Formula 3-I] [Formula 3-II]

[Formula 3-III]

In the above general formulas (III-1) to (III-III)
L ¹⁰ to L ¹² each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹⁰ to R ¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or combinations thereof ,
ET, ET1, and ET2 are each independently selected from substituted or unsubstituted groups listed in Group 3 below,
Wherein HT, HT1 and HT2 are each independently selected from substituted or unsubstituted groups listed in the following group 4:
[Group 3]

,
[Group 4]

,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group and,
In the groups 3 and 4, * is a connection point. The method of claim 6,
Wherein the third compound is selected from the compounds listed in the following Group 5:
[Group 5]
[D-1] [D-2] [D-3] [D-4]

[D-5] [D-6] [D-7] [D-8]

[D-9] [D-10] [D-11] [D-12]

[D-13] [D-14] [D-15] [D-16]

[D-18] [D-19] [D-20] [D-21]

[D-23] [D-24] [D-25] [D-26]

[D-28] [D-29] [D-30] [D-31]

[D-33] [D-34] [D-35] [D-36]

[D-38] [D-39] [D-40] [D-41]

[D-43] [D-44] [D-45] [D-46]

[D-48] [D-49] [D-50] [D-51]

[D-53] [D-54] [D-55] [D-56]

[D-58] [D-59] [D-60] [D-61]

[D-63] [D-64] [D-65] [D-66]

[D-68] [D-69] [D-70] [D-71]

[D-73] [D-74] [D-75] [D-76]

. The method of claim 6,
Wherein the electron transporting auxiliary layer comprises:
At least one of the first compounds represented by the following formulas (1-III) to (1-X); And
An organic optoelectronic device including at least one of a third compound represented by the following general formulas (III-1) to (III-III)
[Chemical Formula 1-III] [Chemical Formula 1-IV]

[Chemical Formula 1-V] [Chemical Formula 1-VI]

[Chemical Formula 1-VII]

[Chemical Formula 1-VIII] [Chemical Formula I-IX]

In the above general formulas (I-III) to (I-IX)
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
W is each independently N, C or CR ^b ,
R ^5a to R ^5d , R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 hetero An aryl group or a combination thereof,
[Formula 3-I] [Formula 3-II]

[Formula 3-III]

In the above general formulas (III-1) to (III-III)
L ¹⁰ to L ¹² each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹⁰ to R ¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or combinations thereof ,
ET, ET1, and ET2 are each independently selected from substituted or unsubstituted groups listed in Group 3 below,
Wherein HT, HT1 and HT2 are each independently selected from substituted or unsubstituted groups listed in the following group 4:
[Group 3]

,
[Group 4]

,
In the groups 3 and 4, * is a connection point,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. The method of claim 9,
Wherein the electron transporting auxiliary layer comprises:
At least one of the first compounds represented by Formulas 1-IV and 1-VII; And
And at least one of the third compounds represented by the general formula (III-III). 3. The method of claim 2,
Wherein the second compound is represented by the following formula (II-1) or (II-II):
[Chemical Formula 2-I] [Chemical Formula 2-II]

In the general formulas (II-1) and (II-II)
X < ¹ > is O or S,
R ⁷ to R ⁹ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 C30 aryloxy groups, substituted or unsubstituted C6 to C30 arylthio groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C2 to C30 amino groups, substituted or unsubstituted C3 to C30 silyl groups , A cyano group, a nitro group, a hydroxyl group or a carboxyl group, or a combination thereof,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,
n7 to n9 each independently represent an integer of 0 to 3,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method of claim 2,
Wherein the second compound is represented by at least one of the following general formulas (II-III) to (II-XI):
[Chemical Formula 2-III] [Chemical Formula 2-IV] Chemical Formula 2-V]

[Chemical Formula 2-VI] [Chemical Formula 2-VII] [Chemical Formula 2-VIII]

[Chemical Formula 2-IX] [Chemical Formula 2-X]

[Chemical Formula 2-XI]

In the above Formulas 2-III to 2-XI,
X ¹ and X ³ are each independently O or S,
X ² is O, S, or CR ⁱ R ^j ,
R ⁷ to R ⁹ and R ^c to R ^j each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 C20 alkoxy group, a substituted or unsubstituted C3 to C20 cycloalkoxy group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 arylthio group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 amino group, A substituted or unsubstituted C3 to C30 silyl group, a cyano group, a nitro group, a hydroxyl group or a carboxyl group,
Ar ¹ and Ar ² each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted Or a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,
n7 to n9 each independently represent an integer of 0 to 3,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method of claim 2,
Ar ¹ and Ar ² in Formula 2 are each independently selected from the group consisting of a substituted or unsubstituted group listed in the following Group 6:
[Group 6]

In the above group 6,
Y is O, S, CR ^l R ^m, R ⁿ SiR ^{o p} or NR ego,
* Is a connection point,
R ^k to R ^p each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aralkyl group, A substituted or unsubstituted C 2 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 2 to C 30 amino group, a substituted or unsubstituted C 3 to C 30 silyl group,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method of claim 2,
Wherein the electron transporting auxiliary layer comprises at least one of the first compounds represented by the following general formulas (1) - (III) to (1-
Wherein the hole transporting auxiliary layer comprises at least one of a second compound represented by the following general formulas (II-III) to (II-XI):
[Chemical Formula 1-III] [Chemical Formula 1-IV]

[Chemical Formula 1-V] [Chemical Formula 1-VI]

[Chemical Formula 1-VII]

[Chemical Formula 1-VIII] [Chemical Formula I-IX]

In the above general formulas (I-III) to (I-IX)
Each Z is independently N, C or CR ^a ,
At least one of Z is N,
W is each independently N, C or CR ^b ,
R ^5a to R ^5d , R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 hetero An aryl group or a combination thereof,
[Chemical Formula 2-III] [Chemical Formula 2-IV] Chemical Formula 2-V]

[Chemical Formula 2-VI] [Chemical Formula 2-VII] [Chemical Formula 2-VIII]

[Chemical Formula 2-IX] [Chemical Formula 2-X]

[Chemical Formula 2-XI]

In the above Formulas 2-III to 2-XI,
X ¹ and X ³ are each independently O or S,
X ² is O, S, or CR ⁱ R ^j ,
R ⁷ to R ⁹ and R ^c to R ^j each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 C20 alkoxy group, a substituted or unsubstituted C3 to C20 cycloalkoxy group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 arylthio group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 amino group, A substituted or unsubstituted C3 to C30 silyl group, a cyano group, a nitro group, a hydroxyl group or a carboxyl group,
Ar ¹ and Ar ² each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted Or a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
L ⁷ to L ⁹ each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,
n7 to n9 each independently represent an integer of 0 to 3,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. The method of claim 14,
Wherein the electron transporting auxiliary layer comprises a first compound represented by the general formulas (1-IV) and (1-VII)
Wherein the hole transporting auxiliary layer comprises at least one of the second compounds represented by the general formulas 2-VII, 2-VIII, 2-X, and 2-XI. The method of claim 14,
Wherein the electron transport assisting layer further comprises a third compound represented by the following general formula (III-III): < EMI ID =
[Formula 3-III]

In the above formula (III-III)
L ¹⁰ to L ¹² each independently represent a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹⁰ to R ¹³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or combinations thereof ,
Wherein HT, HT1 and HT2 are each independently selected from substituted or unsubstituted groups listed in the following group 4:
[Group 4]

,
In the above group 4, * is a connection point,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, Means a C30 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group or a cyano group do. 3. The method of claim 2,
Wherein the hole transporting auxiliary layer is in contact with the hole transporting layer and the light emitting layer,
And the electron transporting auxiliary layer is in contact with the electron transporting layer and the light emitting layer, respectively. The method of claim 1,
Wherein the light emitting layer further comprises a fluorescent dopant. 3. The method according to claim 1 or 2,
Wherein the organic optoelectronic device is selected from the group consisting of an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photoconductor drum, and an organic memory device. A display device comprising the organic optoelectronic device according to any one of claims 1 to 3.

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