KR20160107975A - Organic compound and composition and organic optoelectric device and display device - Google Patents

Abstract

상기 화학식 1에서, X¹, X², Ar¹, L¹, L², R¹ 내지 R¹⁴는 명세서에서 정의한 바와 같다. Organic optoelectronic devices and display devices represented by the following formula (1).
[Chemical Formula 1]

In Formula 1, X ¹ , X ² , Ar ¹ , L ¹ , L ² , and R ¹ to R ¹⁴ are as defined in the specification.

Description

Technical Field [0001] The present invention relates to organic compounds, compositions, organic optoelectronic devices, and display devices.

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 that converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting diode usually has a structure in which an organic layer is interposed between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, , An electron injection layer, and a hole blocking layer.

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

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

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

Another embodiment provides a composition for organic optoelectronic devices comprising the organic compound.

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

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

An embodiment provides an organic compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X ¹ and X ² are each independently O, S or CR ^a R ^b ,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,

L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

R ¹ to R ⁶ , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof,

R ⁷ to R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

R ⁸ to R ¹⁰ are independently present or two adjacent rings are connected to form a ring,

R ¹² to R ¹⁴ are independently present or two adjacent rings are connected to form a ring.

According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first organic compound which is an organic compound and at least one second organic compound which has a carbazole moiety.

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

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

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

1 is a cross-sectional view illustrating an organic light emitting device according to one embodiment,
2 is a cross-sectional view illustrating an organic light emitting device according to another 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, "substituent" means that at least one hydrogen in the substituent or 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 C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, Means a C1 to C10 trifluoroalkyl group such as an alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, and a trifluoromethyl group, or a cyano group .

The substituted or unsubstituted aryl group may be substituted with at least one of the substituted halogen group, hydroxyl group, amino group, C1 to C20 amine group, nitro group, C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group, C3 to C30 heterocyclic group , A C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group such as a trifluoromethyl group, or a cyano group 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.

As used herein, unless otherwise defined, it is meant that at least one heteroatom is contained in one functional group and the remainder is carbon. The heteroatom may be selected from N, O, S, P, and Si.

As used herein, the term "aryl group" refers to a group having one or more hydrocarbon ring aromatic moieties. In general, hydrocarbon ring aromatic moieties are connected by a single bond, and hydrocarbon ring aromatic moieties are directly or indirectly fused Non-aromatic fused rings. The aryl groups include monocyclic, polycyclic or fused polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heterocyclic group "is intended to include a heteroaryl group, and in addition to carbon (C) in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from N, O, S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

More specifically, the substituted or unsubstituted aryl group and / or the substituted or unsubstituted heterocyclic group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, Or an unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group , A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a combination thereof, or a combination thereof, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, May be in a fused form, but are not limited thereto.

In the present invention, the substituted or unsubstituted arylene group or the substituted or unsubstituted heteroarylene group means that there are two linking groups in the substituted or unsubstituted allyl group or the substituted or unsubstituted heteroaryl group defined above, For example, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted naphthalene group, 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 quinphenylene group, a substituted or unsubstituted triphenylene group A substituted or unsubstituted perylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted perylene group, A substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted thiazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, A substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, A substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thienylene group, A substituted or unsubstituted quinolinolene group, a substituted or unsubstituted quinolinolene group, a substituted or unsubstituted quinolinolene group, a substituted or unsubstituted quinolinolene group, a substituted or unsubstituted quinolinolene group, A substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzoxazylene group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzoxazylene group, A substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, , A substituted or unsubstituted carbazolylene group, a combination thereof, or a combination thereof, but is not limited thereto.

In the present invention, the substituted or unsubstituted arylene group or the substituted or unsubstituted heteroarylene group may be substituted or unsubstituted phenylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted terphenylene group, substituted Or an unsubstituted quaterphenylene group, a substituted or unsubstituted naphthalene group, and a substituted or unsubstituted pyrimidine ring group, or a combination thereof.

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.

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

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

[Chemical Formula 1]

In Formula 1,

X ¹ and X ² are each independently O, S or CR ^a R ^b ,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,

L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

R ¹ to R ⁶ , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof,

R ⁷ to R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

R ⁸ to R ¹⁰ are independently present or two adjacent rings are connected to form a ring,

R ¹² to R ¹⁴ are independently present or two adjacent rings are connected to form a ring.

The organic compound includes a triazine core and two fused rings and has a structure in which a triazine core and a phenylene group bonded at a meta position are connected to each other through a linking group.

Since the organic compound includes a triazine core, electrons can be easily received when an electric field is applied, and thus the driving voltage of the device using the organic compound can be lowered.

In addition, the organic compound includes a fused ring that is susceptible to holes and a triazine core that is susceptible to electrons, thereby forming a bipolar structure, so that the flow of holes and electrons can be appropriately balanced, The efficiency of the applied device can be improved.

In particular, by including two phenylene groups bound to the meta position, localization of the triazine core that is susceptible to electrons and electron conjugation rings that are susceptible to holes in the above-described bipolar structure compound, and control of the flow of the conjugated system It is possible to exhibit more excellent bipolar characteristics.

Also, by including two phenylene groups bonded at the meta position, the triplet energy (T1) can be increased to improve the efficiency of the device using the organic compound.

Also, the incorporation of two phenylene groups bonded to the meta position can lower the crystallinity of the organic compound at high temperature, thereby improving the thermal stability of the device to which the organic compound is applied and improving the lifetime.

For example, Ar ¹ in the formula (1) is 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, Or an unsubstituted anthracenyl group.

For example, Ar ¹ in formula (1) may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and the biphenyl group may be a meta-biphenyl group, an ortho-biphenyl group or a para- May be substituted with deuterium, a C1 to C10 silyl group, a C1 to C10 alkyl group, or a halogen group.

For example, L ¹ and L ² in formula (1) may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted naphthalene group.

As an example, the two phenylene groups connected to the triazine core may all be unsubstituted phenylene groups. In this case, R ⁷ to R ¹⁴ in formula (1) may each be hydrogen.

In one example, at least one of the two phenylene groups linked to the triazine core may be a substituted phenylene group, wherein the substitution may be, for example, deuterium, a C1 to C10 alkyl group or a C1 to C10 silyl group.

In one example, at least one of the two phenylene groups linked to the triazine core may have adjacent substituents connected to each other to form a ring. Two adjacent of R ⁸ to R ¹⁰ may be connected to form a ring, for example, R ⁸ and R ⁹ may be connected to form a ring, or R ⁹ and R ¹⁰ may be connected to form a ring. Two adjacent two of R ¹² to R ¹⁴ may be connected to form a ring, for example, R ¹² and R ¹³ may be connected to form a ring, or R ¹³ and R ¹⁴ may be connected to form a ring.

In one example, R ⁷ is hydrogen and two adjacent of R ⁸ to R ¹⁰ may be connected to form a ring.

As an example, R ¹¹ is hydrogen and R ¹² to R ¹⁴ Two adjacent ones of which may be connected to form a ring.

In one example, one of the two phenylene groups linked to the triazine core may be adjacent to each other and may be linked together to form a naphthalene group.

For example, both of the two phenylene groups connected to the triazine core may be connected to adjacent substituents, respectively, to form naphthalene groups.

For example, both substituents around the triazine core may be symmetrical.

The organic compound may be represented, for example, by any of the following formulas (1a) to (1j).

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

[Formula 1g]

[Chemical Formula 1h]

[Formula 1i]

[Chemical Formula 1j]

In the above general formulas (1a) to (1j)

X ¹ , X ² , Ar ¹ , and R ¹ to R ⁶ are each as described above,

R ¹⁵ and R ¹⁶ may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

The organic compound may be, for example, a compound listed in the following Group 1, but is not limited thereto.

[Group 1]

The above-described organic compounds can be applied to organic optoelectronic devices.

The above-mentioned organic compounds can be used alone in an organic layer of an organic optoelectronic device. For example, the above-described organic compound may be used in the light emitting layer of the organic layer existing between the anode and the cathode of the organic optoelectronic device, or in the electron transporting layer of the organic layer existing between the anode and the cathode. Here, the electron transporting auxiliary layer may be a layer adjacent to the light emitting layer.

The above-described organic compounds can be applied to organic optoelectronic devices alone or together with other organic compounds. When the above-mentioned organic compound is used together with other organic compounds, it can be applied in the form of a composition.

Hereinafter, one example of the composition for an organic optoelectronic device including the above-described organic compound will be described.

One example of the composition for the organic optoelectronic device may be a composition comprising the above-mentioned organic compound and at least one organic compound having a carbazole moiety. Hereinafter, the organic compound described above is referred to as a 'first organic compound', and at least one organic compound having a carbazole moiety is referred to as a 'second organic compound'.

The second organic compound may be, for example, a compound represented by the following formula (2).

(2)

In Formula 2,

Y ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof,

Ar ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,

R ¹⁷ to R ²⁰ 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 ,

At least one of R ¹⁷ to R ²⁰ and Ar ² includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group.

The second organic compound represented by the general formula (2) may be represented by one of the following general formulas (2a) to (2c):

(2a)

(2b)

[Chemical Formula 2c]

In the above general formulas (2a) to (2c)

Y ¹ , Y ⁴ and Y ⁵ are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted Or an unsubstituted C2 to C30 heteroarylene group or a combination thereof,

Ar ² And Ar ⁵ 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,

R ¹⁷ to R ²⁰ And R < ²⁵ > to R < ^{36 &} 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 second organic compound represented by Formula 2 may be, for example, a compound listed in Group 2, but is not limited thereto.

[Group 2]

The second organic compound may include one or more selected from the compounds represented by Formula 2.

The second organic compound may be, for example, a compound consisting of a combination of a moiety represented by the following formula (3) and a moiety represented by the following formula (4).

[Chemical Formula 3]

In the above formulas (3) and (4)

Y ² and Y ³ are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, C2-C30 heteroarylene groups or combinations 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 heteroaryl group, or a combination thereof,

R ²¹ to R ²⁴ each independently represent 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 ,

* * Two adjacent of Formula 3 to form a fused ring in conjunction with a two - of Formula 4 does not form the fused ring in Formula 3 are each independently CR ^c,

R ^c is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heteroaryl group, or combinations thereof.

The organic compound composed of the combination of the moiety represented by Formula 3 and the moiety represented by Formula 4 may be a compound listed in Group 3 below, but is not limited thereto.

[Group 3]

The second organic compound may include one or more compounds selected from the group consisting of a combination of the moiety represented by Formula 3 and the moiety represented by Formula 4.

The second organic compound may include a compound represented by Formula 2 and a compound comprising a combination of the moiety represented by Formula 3 and the moiety represented by Formula 4.

The composition may include the first organic compound and the second organic compound in a weight ratio of about 1:10 to 10: 1. For example, the first organic compound and the second organic compound may be present in an amount of about 1: 9, about 2: 8, about 3: 7, about 5: 5, about 7: , About 9: 1 by weight.

The composition may be applied to an organic layer of an organic optoelectronic device, for example, the composition may serve as a host of a light emitting layer. At this time, the first organic compound and the second organic compound are used together to improve the mobility and stability of the charge, thereby further improving the light emitting efficiency and lifetime characteristics.

The composition may further include at least one organic compound in addition to the first organic compound and the second organic compound.

The composition may further comprise a dopant. The dopant may be a red, green or blue dopant, for example a phosphorescent dopant.

The dopant may be a metal complex that emits light by multiple excitation that is excited by a triplet state or higher, and is a substance that emits light by mixing with the first host compound and the second host compound. May be used. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

Examples of the phosphorescent dopant include organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh and Pd or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto.

(Z)

L ₂ MX

In the above formula (Z), M is a metal, L and X are the same or different from each other and are ligands that complex with M.

M may be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, Lt; / RTI >

The compound of the present invention or the composition of the present invention can be applied to an organic layer of an organic optoelectronic device and can be applied to an electron transporting layer located between an emitting layer and an electron transporting layer as an example.

The first compound or the first compound and the second compound-containing composition may be applied to the electron transporting layer to control the electron transporting ability from the electron transporting layer to the light emitting layer, and by balancing the electron transporting ability with the electron transporting ability of the light emitting layer, It is possible to prevent electrons from accumulating in the cathode. Further, the electron transporting auxiliary layer converts the holes and / or excitons generated from the anode to the light emitting layer and / or the excitons generated in the light emitting layer into the excitons having energy lower than the energy of the excitons of the light emitting layer, Can be effectively blocked. Thus, the efficiency and lifetime of the organic optoelectronic device can be improved. The first compound and the second compound may be included, for example, in a weight ratio of about 1:99 to 99: 1.

The organic compound and / or the composition may be formed by a dry film forming method or a solution process. The dry film forming method may be, for example, a chemical vapor deposition method, sputtering, plasma plating, or ion plating, and two or more compounds may be simultaneously deposited or a compound having the same deposition temperature may be mixed to form a film. The solution process may be, for example, ink jet printing, spin coating, slit coating, bar coating and / or dip coating.

Hereinafter, the organic compound or the organic optoelectronic device to which the above-described composition is applied will be described.

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

The organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the organic compound described above or the composition described above.

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

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

1, an organic optoelectronic device 200 according to an embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 located between the anode 110 and the cathode 120 .

The anode 110 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 120 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al and BaF ₂ / Ca.

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

The light emitting layer 130 may include, for example, the above-described organic compounds alone, or may be a mixture of at least two of the organic compounds described above, and may include the above-described composition.

The organic layer 105 includes an auxiliary layer 140 positioned between the light emitting layer 130 and the cathode 120. The auxiliary layer 140 may facilitate charge injection and movement between the cathode 120 and the light emitting layer 130. [

2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.

2, an organic optoelectronic device 300 according to another embodiment includes an anode 110 and a cathode 120 facing each other, and an anode 110 and a cathode 120, which are disposed between the anode 110 and the cathode 120, And the organic layer 105 includes a light emitting layer 130 and an auxiliary layer 140. The light emitting layer 130 and the auxiliary layer 140 are formed on the organic layer 105,

However, this embodiment differs from the above-described embodiment in that the auxiliary layer 140 includes a first auxiliary layer 141 located adjacent to the cathode 120 and a second auxiliary layer 142 located adjacent to the emitting layer 130 ). The above-described organic compound or the above-described composition may be included in the second auxiliary layer 142 located adjacent to the light emitting layer 130.

The organic thin film layer 105 may further include at least one auxiliary layer positioned between the anode 110 and the light emitting layer 130 in FIG. 1 or FIG.

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

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

The starting materials and reaction materials used in the synthesis examples and examples described below were purchased from Sigma-Aldrich or TCI unless otherwise stated, or synthesized by known methods.

Intermediate Synthetic example

Synthetic example  1: Synthesis of intermediate L-1

[Reaction Scheme 1]

30 g (162.68 mmol) of 2,4,6-trichloro-1,3,5-triazine are dissolved in 325 ml of solvent tetrahydrofuran in a 500 ml flask. Cool the solvent using ice water and slowly drop 54.23 ml (162.68 mmol) of phenylmagnesium bromide using a dropping funnel under a nitrogen stream. 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 further stirred with 100 ml of hexane and then filtered to obtain Intermediate L-1 (27 g, 73% yield).

The result of elemental analysis of the synthesized intermediate L-1 is shown below.

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  2: Synthesis of Compound L-2

[Reaction Scheme 2]

To a 1000 ml flask was added 50.0 g (219.23 mmol) of the intermediate dibenzo [b, d] thiophen-4-ylboronic acid, 80.63 g (285.00 mmol) of 1- bromo 3-iodobenzene, 60.60 g (438.46 mmol) after _{semi-PPh 3) 4 (Tetrakis (triphenylphosphine} ) palladium (0)) into a 12.67g (10.96mmol) in tetrahydrofuran, 450mL, 200mL of water, was heated to reflux for 12 hours under a nitrogen stream. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, and the filtrate was washed with dichloromethane and silica gel / celite. An appropriate amount of an organic solvent was removed, and the residue was recrystallized from methanol to obtain Intermediate L-2 (45.21 g, 74 % Yield).

The result of elemental analysis of the synthesized intermediate L-2 is shown below.

calcd. _{C 18 H 11 BrS: C,} 63.73; H, 3.27; Br, 23.55; S, 9.45; Found: C, 63.69; H, 3.26; Br, 23.57; S, 9.52;

Synthetic example  3: Synthesis of intermediate L-3

[Reaction Scheme 3]

Intermediate 1000ml flask L-2 50.0g (147.38mmol), boronic ester 56.14g (221.08mmol), potassium acetate 36.16g (98.14mmol), Pd (dppf ) Cl 2 gave put 6.02g (7.37mmol) in toluene 500mL The mixture was heated under reflux in a nitrogen stream for 12 hours. The resulting solid was dissolved in dichloromethane, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The resulting residue was recrystallized from a nucleic acid to obtain Intermediate L-3 (38.62 g, 68% yield).

The result of elemental analysis of the synthesized intermediate L-3 is shown below.

calcd. C ₂₄ H ₂₃ BO ₂ S: C, 74.62; H, 6.00; B, 2.80; O, 8.28; S, 8.30; Found: C, 74.60; H, 6.03; B, 2.81; 8.23; S, 8.31;

Synthetic example  4: Intermediate L- 4 of  synthesis

Intermediate L-4 shown as a more specific example of the compound of the present invention was synthesized in the same manner as L-1 of Synthesis Example 1

[Reaction Scheme 4]

Synthetic example  5, 6: Intermediate L-5, L- 6 of  synthesis

Intermediates L-5 and L-6 shown as more specific examples of the compound of the present invention were synthesized in the same manner as L-2 and L-3 of Synthesis Examples 2 and 3

[Reaction Scheme 5]

[Reaction Scheme 6]

Of the final compound Synthetic example

Synthetic example  7: Synthesis of Compound A-5

[Reaction Scheme 7]

Intermediates in 250mL flask L-1 5.0g (22.12mmol), L-3 18.80g (48.66mmol), potassium carbonate 7.64g (55.30mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine) palladium (0)) 1.28 g (1.11 mmol) were added to 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (500 mL), and the crystallized solid was filtered, and the filtrate was dissolved in monochlorobenzene. The filtrate was filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Compound A- 81% yield).

The result of elemental analysis of the synthesized Compound A-5 is as follows.

calcd. C ₄₅ H ₂₇ N ₃ S ₂ : C, 80.21; H, 4.04; N, 6.24; S, 9.52; Found: C, 80.24; H, 4.08; N, 6.21; S, 9.51;

Synthetic example  8: Synthesis of Compound A-1

[Reaction Scheme 8]

Intermediates in 250mL flask L-1 5.0g (22.12mmol), L-5 18.02g (48.66mmol), potassium carbonate 7.64g (55.30mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine) palladium (0)) 1.28 g (1.11 mmol) were added to 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (500 mL), and the crystallized solid was filtered, and the filtrate was dissolved in monochlorobenzene. The filtrate was filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain Compound A- 72% yield).

The result of the elemental analysis of the synthesized Compound A-1 is as follows.

calcd. C ₄₅ H ₂₇ N ₃ O ₂ : C, 84.22; H, 4.24; N, 6.55; 0, 4.99; Found: C, 84.21; H, 4.21; N, 6.51; , 4.97

Synthetic example  9: Synthesis of Compound A-7

[Reaction Scheme 9]

Intermediates in 250mL flask L-1 5.0g (22.12mmol), L-6 18.80g (48.66mmol), potassium carbonate 7.64g (55.30mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine) palladium (0)) 1.28 g (1.11 mmol) were added to 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting solid was dissolved in monochlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain Compound A-7 (11.24 g, 75% yield).

The result of elemental analysis of the synthesized compound A-7 is as follows.

calcd. C ₄₅ H ₂₇ N ₃ S ₂ : C, 80.21; H, 4.04; N, 6.24; S, 9.52; Found: C, 80.22; H, 4.04; N, 6.25; S, 9.53;

Synthetic example  10: Synthesis of Compound A-25

[Reaction Scheme 10]

Intermediates in 250mL flask L-4 7.0g (23.17mmol), L-5 18.87g (50.97mmol), potassium carbonate 8.0g (57.92mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine) palladium (0)) 1.34 g (1.16 mmol) were added to 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux under heating in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (500 mL), and the crystallized solid was filtered, and then dissolved in monochlorobenzene. The mixture was filtered with silica gel / celite, and an organic solvent was removed in an appropriate amount, and then recrystallized from methanol to obtain Compound A- 73% yield).

The result of elemental analysis of the synthesized Compound A-25 is as follows.

calcd. C ₅₁ H ₃₁ N ₃ O ₂ : C, 85.34; H, 4.35; N, 5.85; O, 4.46; Found: C, 85.31; H, 4.33; N, 5.84; 4.47;

Synthetic example  11: Synthesis of Compound E-1

[Reaction Scheme 11]

Synthesis of intermediate E

In a 1000 mL round flask, 39.99 g (156.01 mmol) of indolocarbazole, 26.94 g (171.61 mmol) of bromobenzene, 22.49 g (234.01 mmol) of sodium t-butoxide and 4.28 g (4.68 mmol) and 2.9 mL (50% in toluene) of tri-t-butylphosphine were mixed with 500 mL of xylene and heated under reflux for 15 hours under a nitrogen stream. The resulting solid was dissolved in dichlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount, followed by recrystallization from methanol to obtain Intermediate E (23.01 g, 44 % Yield).

The result of elemental analysis of the synthesized intermediate E is as follows.

calcd. C ₂₄ H ₁₆ N ₂ : C, 86.72; H, 4.85; N, 8.43; Found: C, 86.72; H, 4.85; N, 8.43

Synthesis of Compound E-1

The following reaction was carried out in a 500 mL round flask with 22.93 g (69.03 mmol) of intermediate E, 11.38 g (72.49 mmol) of bromobenzene, 4.26 g (75.94 mmol) of potassium hydroxide, 13.14 g And 6.22 g (34.52 mmol) of 10-phenanthroline were placed in 230 mL of DMEF and heated under reflux for 15 hours under a nitrogen stream. The resultant mixture was added to 1000 mL of methanol and the resulting solid was filtered and dissolved in dichlorobenzene, filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount, followed by recrystallization from methanol to obtain Compound E-1 (12.04 g , 43% yield).

The result of the elemental analysis of the synthesized compound E-1 is as follows.

calcd. _{C 30 H 20 N 2: C} , 88.21; H, 4.93; N, 6.86; Found: C, 88.21; H, 4.93; N, 6.86

Synthetic example  12: Synthesis of compound B-43

[Reaction Scheme 12]

(37.66 mmol) of 3-bromo-N-methabiphenylcarbazole and 16.77 g (37.66 mmol) of 3-canonic acid N-biphenylcarbazole were added to a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere, And tetrahydrofuran: To a mixture of 200 mL of toluene (1: 1) and 100 mL of a 2M potassium carbonate aqueous solution, 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added and heated for 12 hours in a nitrogen stream Lt; / RTI > After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was dissolved in 500 mL of chlorobenzene, and the solution was then subjected to silica gel filtration and the solvent was completely removed. The solvent was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 16.07 g (yield 67%) of Compound B-43 .

The result of the elemental analysis of the synthesized compound B-43 is as follows.

calcd. C ₄₈ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; found: C, 90.71; H, 5.01; N, 4.27

Comparative Synthetic Example  One: CBP Synthesis of

4,4-N, N-dicarbazolebiphenyl (CBP) represented by the following formula a was synthesized by the same method as described in International Publication WO 2013032035.

(A)

Comparative Synthetic Example  2: Synthesis of C-1

Compound C-1 represented by the following formula (b) was synthesized by the same method as described in International Publication No. US2014 / 0001456A1.

[Formula b]

Comparative Synthetic Example  3: Synthesis of C-2

Compound C-2 represented by the following formula (c) was synthesized by the same method as described in International Publication No. US2014 / 0001456A1 (only an intermediate was changed).

(C)

Preparation of Organic Light Emitting Device I

Comparative Example  One

Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance value of 15? / Cm ² is cut into a size of 50 mm x 50 mm x 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was performed for 30 minutes.

The ITO transparent electrode thus prepared was vacuum evaporated on the ITO substrate by using a 1000 Å thick anode as an anode to form a 1200 Å thick hole injection layer.

4,4-N, N-dicarbazolebiphenyl (CBP) prepared in Comparative Synthesis Example 1 was used as a host in the light emitting layer, doped with PhGD compound as a phosphorescent green dopant in an amount of 10% by weight, Emitting layer was formed.

Thereafter, the following BAlq [Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum] 50 angstroms and Alq3 [Tris (8-hydroxyquinolinato) aluminum ] 350 < / RTI > were sequentially laminated to form an electron transporting layer.

LiF 5 Å and Al 1000 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

[HTM] [PhGD]

[BAlq] [Alq3]

Example  One

Except that the compound A-5 prepared in Synthesis Example 7 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, .

Example  2

Except that the compound A-1 prepared in Synthesis Example 8 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, .

Example  3

Except that the compound A-7 prepared in Synthesis Example 9 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, .

Example  4

Except that the compound A-25 prepared in Synthesis Example 10 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, .

Comparative Example  2

Except that the compound C-1 prepared in Comparative Synthesis Example 2 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, Device.

Comparative Example  3

Except that the compound C-2 prepared in Comparative Synthesis Example 3 was used instead of the 4,4-N, N-dicarbazole biphenyl (CBP) prepared in Comparative Synthesis Example 1, Device.

Evaluation of Organic Light Emitting Diodes I

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting device according to Examples 1 to 4 and Comparative Examples 1 to 3 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 1.

(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) Current efficiency measurement

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 5000 cd / m ² and the current efficiency (cd / A) decreased to 90% was measured and the results were obtained.

No. Emitting layer host The driving voltage (V) Color (EL color) Efficiency (cd / A) T ₉₀ Life (hr)
@ 5000 cd / m ² Example 1 A-5 4.21 Green 58.5 320 Example 2 A-1 4.23 Green 57.4 315 Example 3 A-7 4.43 Green 50.4 270 Example 4 A-25 4.31 Green 57.0 295 Comparative Example 1 CBP 6.70 Green 34.8 50 Comparative Example 2 C-1 4.53 Green 53.7 110 Comparative Example 3 C-2 4.44 Green 51.2 160

According to Table 1, the organic light emitting devices according to Examples 1 to 4 have a lower driving voltage and a luminous efficiency of about 1.5 times higher than those of the organic light emitting devices according to Comparative Examples 1 to 3. Specifically, the organic light emitting device according to each of Examples 1 to 4 has a significantly improved driving voltage, luminous efficiency, and lifetime as compared with Comparative Example 1. Also, the organic light emitting devices according to Examples 1 to 4 can lower the crystallinity at high temperature by using the light emitting layer host including two phenylene groups bonded at the meta position, and accordingly, the organic light emitting device according to Comparative Examples 2 and 3 It can be confirmed that the lifetime characteristics are remarkably improved.

Manufacture of organic light emitting device II

Example  5

(Ppy) ₃ was formed as a light emitting layer dopant on the hole transport layer to a thickness of 40 ANGSTROM, and the compound A-5 (first host) prepared in Synthesis Example 7 and the compound E-1 ) Was co-deposited at a weight ratio of 5: 5 to form a layer having a thickness of 360 Å, thereby forming a light emitting layer. Thus, an organic light emitting device was manufactured.

Example  6

An organic luminescent device was prepared in the same manner as in Example 5 except that the compound A-5 and the compound E-1 as the host of the light emitting layer were notarized at a weight ratio of 3: 7.

Example  7

An organic luminescent device was prepared in the same manner as in Example 5 except that the compound A-5 and the compound E-1 as the host of the light emitting layer were notarized at a weight ratio of 7: 3.

Example  8

An organic light emitting device was prepared in the same manner as in Example 5 except that the compound A-5 as the host of the light emitting layer and the compound B-43 prepared in Synthesis Example 12 were notarized at a weight ratio of 5: 5.

Example  9

An organic light emitting device was prepared in the same manner as in Example 5, except that the compound A-5 as a host for the light emitting layer and the compound B-43 prepared in Synthesis Example 12 were notarized at a weight ratio of 3: 7.

Example  10

An organic light emitting device was prepared in the same manner as in Example 5 except that the compound A-5 as a host of the light emitting layer and the compound B-43 prepared in Synthesis Example 12 were notarized at a weight ratio of 7: 3.

Example  11

Except that the compound A-1 prepared in Synthesis Example 8 and the compound B-43 prepared in Synthesis Example 12 were used as the host of the light emitting layer in a weight ratio of 5: 5, to prepare an organic light emitting device Respectively.

Example  12

Except that the compound A-1 prepared in Synthesis Example 8 and the compound B-43 prepared in Synthesis Example 12 were used as the host of the light emitting layer and the mixture was not diluted in a weight ratio of 3: 7 to prepare the organic light emitting device Respectively.

Example  13

An organic light-emitting device was produced in the same manner as in Example 5 except that the compound A-1 prepared in Synthesis Example 8 and the compound B-43 prepared in Synthesis Example 12 were used as hosts for the light-emitting layer, Respectively.

Evaluation of organic light emitting device II

The driving voltage, current efficiency and lifetime of the organic light emitting devices according to Examples 5 to 13 were measured.

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 (Kethley SMU 236) while increasing 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

The resulting organic light emitting device was measured for brightness using a luminance meter (PR650 Spectroscan Source Measurement Unit, manufactured by PhotoResearch) while raising the voltage from 0 V to 10 V, and the result was obtained.

(3) Current efficiency measurement

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 initial brightness (cd / m2) of the 5000cd / m ² as a light emitting and measuring the reduction in the luminance over time, the luminance is reduced to 90% of the initial luminance was measured by a time T ₉₀ life.

The first host Second host First host:
Second host
Ratio (wt / wt) Driving voltage
(V) efficiency
(cd / A) T ₉₀ Life (hr) Example 5 Compound A-5 Compound E-1 5: 5 4.13 59.1 355 Example 6 Compound A-5 Compound E-1 3: 7 4.31 60.1 375 Example 7 Compound A-5 Compound E-1 7: 3 4.11 57.1 330 Example 8 Compound A-5 Compound B-43 5: 5 4.07 60.2 385 Example 9 Compound A-5 Compound B-43 3: 7 4.5 61.5 405 Example 10 Compound A-5 Compound B-43 7: 3 4.18 59.8 350 Example 11 Compound A-1 Compound B-43 5: 5 4.2 57.2 375 Example 12 Compound A-1 Compound B-43 3: 7 4.38 58.5 395 Example 13 Compound A-1 Compound B-43 7: 3 4.26 56.8 345

According to Table 2, it can be seen that the organic light emitting devices according to Examples 5 to 13 have a relatively low driving voltage, a high current efficiency and a long life characteristic.

Manufacture of organic light emitting device III

Example  14

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator. HT13 was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a hole injection and transport layer having a thickness of 1400A. A blue fluorescent light emitting host and dopant, 9,10-di (2-naphthyl) anthracene (ADN) and BD01 were doped with 5 wt% and vacuum deposition was performed to form a light emitting layer having a thickness of 200 Å. The structures of ADN and BD01 are shown below. Thereafter, the compound A-5 prepared in Synthesis Example 7 was co-deposited on the light-emitting layer to form an electron transporting layer having a thickness of 50 Å. Tris (8-hydroxyquinoline) aluminum (Alq3) was vacuum deposited on the electron transporting auxiliary layer to form an electron transporting layer having a thickness of 310 A, and Liq 15 A and Al 1200 A were successively vacuum-deposited on the electron transporting layer to form a cathode Thereby preparing an organic light emitting device.

The organic light emitting device has a structure having five organic thin film layers. Specifically,

Alq3 / Liq (15 ANGSTROM) / Al (1200 ANGSTROM) was formed on the ITO / HT13 (1400 Å) / EML [ADN: BD01 = 95: 5 wt%] (200 Å) .

[AND] [BD01]

Example  15

An organic light emitting device was prepared in the same manner as in Example 14, except that Compound A-1 prepared in Synthesis Example 8 was used instead of Compound A-5 in the electron transporting auxiliary layer.

Example  16

An organic luminescent device was prepared in the same manner as in Example 14, except that Compound A-7 prepared in Synthesis Example 9 was used instead of Compound A-5 in the electron transporting auxiliary layer.

Example  17

An organic light emitting device was prepared in the same manner as in Example 14 except that Compound A-25 prepared in Synthesis Example 10 was used in place of Compound A-5 in the electron transporting auxiliary layer.

Comparative Example  4

An organic light emitting device was prepared in the same manner as in Example 14 except that the electron transporting auxiliary layer was not used.

Evaluation of organic light emitting device III

The current density change, the luminance change and the luminous efficiency of the organic luminescent devices according to Examples 14 to 17 and Comparative Example 4 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 3.

(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).

 (5) Life measurement

The initial luminance (cd / m ²⁾ was emitted at 750 cd / m ² using a Polarronix lifetime measuring system for the manufactured organic light emitting device, and the decrease in luminance over time was measured, and the luminance was reduced to 97% _Was measured by T ₉₇ lifetime.

device Electron transporting auxiliary layer Driving voltage Luminous efficiency The color coordinates (x, y) T ₉₇ Life (hr) Example 14 Compound A-5 5.04 6.8 (0.133, 0.149) 205 Example 15 Compound A-1 5.06 6.7 (0.133, 0.149) 195 Example 16 Compound A-7 5.08 6.4 (0.133, 0.149) 185 Example 17 Compound A-25 5.12 6.6 (0.133, 0.149) 190 Comparative Example 4 not used 5.08 6.8 (0.133, 0.146) 120

According to Table 3, the organic light emitting devices according to Examples 14 to 17 have the same or improved driving voltage and luminous efficiency as those of the organic light emitting device according to Comparative Example 4, and the lifetime is improved by about 1.5 times or more . From this, it can be confirmed that lifetime characteristics of the organic light emitting device can be improved by the electron transporting auxiliary layer containing the compound according to the present invention.

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.

200, 300: Organic light emitting device
105: organic layer
110: anode
120: cathode
130: light emitting layer
140: auxiliary layer
141: first auxiliary layer
142: second auxiliary layer

Claims (16)

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

In Formula 1,
X ¹ and X ² are each independently O, S or CR ^a R ^b ,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R ¹ to R ⁶ , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof,
R ⁷ to R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,
R ⁸ to R ¹⁰ are independently present or two adjacent rings are connected to form a ring,
R ¹² to R ¹⁴ are independently present or two adjacent rings are connected to form a ring.
The method of claim 1,
Ar ¹ represents 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 or a substituted or unsubstituted anthracenyl group Organic compounds.
The method of claim 1,
And R ⁷ to R ¹⁴ are each hydrogen.
The method of claim 1,
R ⁷ is hydrogen and two adjacent of R ⁸ to R ¹⁰ are connected to form a ring.
The method of claim 1,
R ¹¹ is hydrogen and R ¹² to R ¹⁴ Wherein two adjacent rings are connected to form a ring.
The method of claim 1,
An organic compound represented by any one of the following formulas (1a) to (1j):
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

[Formula 1g]

[Chemical Formula 1h]

[Formula 1i]

[Chemical Formula 1j]

In the above general formulas (1a) to (1j)
X ¹ and X ² are each independently O, S or CR ^a R ^b ,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
R ¹ to R ⁶ , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof,
R ¹⁵ and R ¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or combinations thereof.
The method of claim 1,
Organic compounds listed in group 1 below:
[Group 1]

A first organic compound according to any one of claims 1 to 7, and
At least one second organic compound having a carbazole moiety
Wherein the organic photovoltaic device further comprises:
9. The method of claim 8,
The second organic compound
1. A composition for an organic optoelectronic device comprising at least one compound selected from the group consisting of a compound represented by the following formula (2) and a moiety represented by the following formula (3) and a moiety represented by the following formula (4)
(2)

In Formula 2,
Y ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof,
Ar ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R ¹⁷ to R ²⁰ 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 ,
At least one of R ¹⁷ to R ²⁰ and Ar ² includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group,
[Chemical Formula 3]

In the above formulas (3) and (4)
Y ² and Y ³ are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, C2-C30 heteroarylene groups or combinations 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 heteroaryl group, or a combination thereof,
R ²¹ to R ²⁴ each independently represent 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 ,
* * Two adjacent of Formula 3 to form a fused ring in conjunction with a two - of Formula 4 does not form the fused ring in Formula 3 are each independently CR ^c,
R ^c is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heteroaryl group, or combinations thereof.
The method of claim 9,
Wherein the second organic compound represented by Formula 2 is represented by at least one of the following Chemical Formulas 2a to 2c:
(2a)

(2b)

[Chemical Formula 2c]

In the above general formulas (2a) to (2c)
Y ¹ , Y ⁴ and Y ⁵ are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted Or an unsubstituted C2 to C30 heteroarylene group or a combination thereof,
Ar ² And Ar ⁵ 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,
R ¹⁷ to R ²⁰ And R < ²⁵ > to R < ^{36 &} 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.
9. The method of claim 8,
A composition for an organic optoelectronic device further comprising a phosphorescent dopant.
The anode and the cathode facing each other, and
At least one organic layer positioned between the anode and the cathode
/ RTI >
Wherein the organic layer comprises the organic compound according to claim 1 or the composition according to claim 8.
The method of claim 12,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the organic compound or the composition.
The method of claim 12,
The organic layer
A light emitting layer, and
The auxiliary layer located between the light emitting layer and the cathode
/ RTI >
Wherein the auxiliary layer comprises the organic compound or the composition.
The method of claim 14,
The auxiliary layer
A first auxiliary layer located adjacent to the cathode, and
A second auxiliary layer positioned adjacent to the light emitting layer,
/ RTI >
Wherein the organic compound or the composition is contained in the second auxiliary layer
Organic optoelectronic devices.
13. A display device comprising the organic opto-electronic device according to claim 12.

Images