KR20180000622A - Organic compound for optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to an organic compound for an organic optoelectronic device represented by chemical formula 1, and an organic optoelectronic device and a display device using the same. The details of the chemical formula 1 are as defined in the specification. One embodiment of the present invention provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with high-efficiency and long-life. Another embodiment of the present invention provides an organic optoelectronic device including the compound for the organic optoelectronic device.

Description

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

A compound for an organic optoelectronic device, an organic optoelectronic device and a display device.

An organic optoelectronic diode is an element that can switch between electric energy and light energy.

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

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

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

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

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

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

Another embodiment provides an organic optoelectronic device including the compound for the organic optoelectronic device.

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

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

[Chemical Formula 1]

In Formula 1,

L is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

R ¹ to R ⁹ each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C40 silyl group, a substituted or unsubstituted C6 to C30 aryl group, Lt; / RTI >

Each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted carbazolyl group,

Means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C4 alkyl group, or a C6 to C18 aryl group.

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 optoelectronic device including the above- do.

According to another embodiment, there is provided a display device including the organic optoelectronic device.

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

1 and 2 are cross-sectional views illustrating an organic light emitting 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 hydrogen in the substituent or compound is replaced with 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 C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 aryl group, A C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

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

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

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

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

As used herein, the term " aryl group "refers to a grouping of groups having one or more hydrocarbon aromatic moieties,

A structure in which all the elements of the hydrocarbon aromatic moiety have a p-orbital and these p-orbital forms a conjugation, such as a phenyl group and a naphthyl group,

A structure in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarter-phenyl group,

Two or more hydrocarbon aromatic moieties may also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term "heteroaryl group" means that the aryl group contains 1 to 3 hetero atoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused together. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, A substituted or unsubstituted thienyl 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 fluorenyl 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 furanyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, , A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted 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 benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted A substituted or unsubstituted dibenzothiophenyl group, or a combination thereof. The term " substituted or unsubstituted benzothiophenylene group " 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.

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

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

[Chemical Formula 1]

In Formula 1,

L is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

R ¹ to R ⁹ each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C40 silyl group, a substituted or unsubstituted C6 to C30 aryl group, Lt; / RTI >

Each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted carbazolyl group,

Means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C4 alkyl group, or a C6 to C18 aryl group. In one embodiment of the present invention, the term "substituted" means that at least one hydrogen is substituted with a phenyl group or a biphenyl group.

The compound represented by the formula (1) is a structure in which an indole moiety and a carbazole moiety are connected to each other through a linking group "L".

The formula 1 may be represented by the following formula 1-I or 1-II according to the point at which the linking group "L" is connected to the indole moiety.

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

In Formulas I-I and I-II, L, R ¹ to R ⁹ , and Ar ¹ to Ar ³ are as described above.

The above formula (1) includes the linking group "L " to enhance the hole flow characteristics through expansion of the hole region.

Particularly, L represents a carbon (C) position adjacent to N in the pentagonal ring of the indole moiety or a carbon (C) position facing N in the pentagonal ring of the indole moiety as shown in the above formula (1-II) The molecular structure is stabilized and the effect of charge mobility can be improved.

The L may be a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof. Specifically, the L may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted bicycle Substituted or unsubstituted dibenzothiophenylene groups, substituted or unsubstituted dibenzothiophenylene groups, substituted or unsubstituted dibenzothiophenylene groups, substituted or unsubstituted dibenzothiophenylene groups, substituted or unsubstituted dibenzothiophenylene groups, A phenylene group, or a substituted or unsubstituted pyridylenyl group, and more specifically may be selected from the linking groups listed in the following Group I, but the present invention is not limited thereto.

[Group I]

In the above group I, * is a connection point with a neighboring atom.

In one embodiment of the present invention, L may be a single bond, a phenylene group, or a biphenylene group.

In a specific embodiment of the present invention, L may be a para-phenylene group, or a meta-phenylene group.

The Ar ¹ to Ar ³ may each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and the carbazolyl group substituted or unsubstituted in Ar ¹ to Ar ³ Are excluded.

On the other hand, since the substituent at the positions of Ar ¹ and Ar ² is an aryl group other than hydrogen or a heteroaryl group, the lifetime characteristics of the device can be improved because it is relatively superior in terms of thermal stability as compared with a compound in which the substituent is hydrogen.

Specifically, each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorene A substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group , A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinolinyl group, more specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group , A substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, Or an unsubstituted quinazolinyl group.

For example, substituents listed in the following Group II, but are not limited thereto.

[Group II]

In the above group II, * is a connection point.

In one embodiment of the present invention, Ar ¹ to Ar ³ each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazoline Lt; / RTI >

In one specific embodiment of the present invention, Ar ¹ and Ar ² are each independently a phenyl group or a biphenyl group, and Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted Triazinyl groups, and substituted or unsubstituted quinazolinyl groups.

In one embodiment of the present invention, R ¹ to R ⁹ each independently represent hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C4 alkyl group, substituted or unsubstituted C1 to C10 silyl group, substituted or unsubstituted A C6 to C18 aryl group, or a combination thereof,

In a specific embodiment of the present invention, R ¹ to R ⁹ are each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C4 alkyl groups, substituted or unsubstituted C6 to C18 aryl groups, Lt; / RTI > For example, R ¹ to R ⁹ each independently may be hydrogen, deuterium, methyl, ethyl, iso-propyl, tert-butyl, phenyl, naphthyl or biphenyl.

More specifically, R ¹ to R ⁹ each independently may be hydrogen, deuterium, a methyl group, a phenyl group, a naphthyl group or a biphenyl group.

In the most specific embodiment of the present invention, L is a para-phenylene group or a meta-phenylene group, and each of R ¹ to R ⁹ may independently be hydrogen or a phenyl group, and each of Ar ¹ to Ar ³ is A substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazolinyl group.

For example, R ⁵ to R ⁹ may all be hydrogen. When all of R ⁵ to R ⁹ are hydrogen, the molecular structure is close to the plate shape, and the electron flow is strengthened.

The compound for an organic optoelectronic device may be selected from the compounds listed in the following Group 1, but is not limited thereto.

[Group 1]

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

[5] [6] [7] [8]

[9] [10] [11] [12]

[13] [14] [15] [16]

[17] 18 [19] [20]

[21] 22 [23] [24]

[25] 26 [27] [28]

[29] [30] [31] [32]

[33] [34] [35] [36]

[37] 38 [39] [40]

[41] [42] [43] [44]

[45] 46 [47] [48]

[49] 50 [51] [52]

[53] [54] 55 [56]

[57] 58 [59] [60]

[61] 62 [63] [64]

[65] 66 [67] [68]

[69] 70 [71] [72]

Hereinafter, an organic optoelectronic device according to another 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 into each other. Examples of the organic optoelectronic device include an organic light emitting device, an organic light emitting device, an organic solar cell, and an organophotoreceptor drum.

The organic optoelectronic devices according to other embodiments 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 above-described organic optoelectronic device compound .

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

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

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

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

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

The organic layer 105 includes the light emitting layer 130 including the compound for the organic optoelectronic device described above.

The light emitting layer 130 may include, for example, the compound for organic optoelectronic devices described above alone, or may include at least two of the compounds for organic optoelectronic devices described above, or may include the composition for the organic optoelectronic device described above .

The compound for an organic optoelectronic device according to an embodiment of the present invention may be included as a host of a light emitting layer, for example, and may be included as a green host as a most specific example.

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

In one embodiment of the present invention, the organic layer 105 may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like, as shown in FIG. 1 or 2.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then forming an organic layer by a dry film forming method such as evaporation, sputtering, plasma plating, or ion plating, A negative electrode or a positive electrode.

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

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

(Synthesis of compound for organic optoelectronic device)

Hereinafter, the starting materials and the reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise stated, and they are easily synthesized with known materials.

In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

The compound of the above formula 3, which is presented as a more specific example of the compound for organic optoelectronic devices of the present invention, was synthesized by the following reaction schemes.

Synthesis Example 1: Synthesis of Compound 3

Compound 3 shown as a more specific example of the compound of the present invention was synthesized through the route of the following four steps.

Step 1 : Synthesis of intermediate A-1

To a 1000 mL flask were added 10.0 g (36.75 mmol) of 2- (4-bromophenyl) indole, 1.1 eq of (9-phenyl-9H-carbazol- Phosphine) 0.05 eq of palladium, 200 mL of THF and 100 mL of water, and the mixture was stirred at 90 DEG C overnight.

After confirming the completion of the reaction by TLC, the reaction mixture was cooled and the organic layer was separated. The solvent was removed under reduced pressure, and 13.7 g (yield: 86%) of Intermediate A-1 was obtained through the column.

Step 2 : Synthesis of intermediate A-2

To a 250 mL flask was added 10.0 g (23.01 mmol) of Intermediate A-1, 1.2 eq of iodobenzene, 0.03 eq of tris (dibenzylideneacetone) dipalladium, 0.15 eq of tridetrabutylphosphine, 1.5 eq of sodium dodecylsulfoxide, And stirred at 110 ° C overnight. After confirming the completion of the reaction by TLC and cooling, the organic layer was separated and the solvent was removed under reduced pressure, and 9.5 g (yield: 81%) of Intermediate A-2 was obtained through the column.

Step 3 : Synthesis of intermediate A-3

10.0 g (19.58 mmol) of Intermediate A-2, 1 eq of NBS and 300 ml of tetrahydrofuran were added to a 1000 mL flask and stirred. After the completion of the reaction was confirmed by TLC, the solvent was removed under reduced pressure, and 7.6 g (yield: 66%) of Intermediate A-3 was obtained through the column.

Step 4 : Synthesis of Compound 3

To a 500 mL flask was added 10.0 g (16.96 mmol) of Intermediate A-3, 1.1 eq of phenylboronic acid, 2.2 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium, 200 mL of THF and 100 mL of water, lt; / RTI >

After confirming the completion of the reaction by TLC, the reaction mixture was cooled, and the organic layer was separated. The solvent was removed under reduced pressure, and 7.5 g (yield: 75%) of Compound 3 was obtained through the column.

Synthetic example  2: Synthesis of Compound 6

Compound 6 shown as a more specific example of the compound of the present invention was synthesized through the same route as Synthesis Example 1 above.

Step 1 : Synthesis of Intermediate B-1

1.1 eq of (9-phenyl-9H-carbazol-2-yl) boronic acid, 2.2 eq of potassium carbonate, Phosphine) 0.05 eq of palladium, 200 mL of THF and 100 mL of water, and the mixture was stirred at 90 DEG C overnight.

After confirming the completion of the reaction by TLC, the reaction mixture was cooled and the organic layer was separated. The solvent was removed under reduced pressure, and 11.9 g (yield: 75%) of Intermediate B-1 was obtained through the column.

Intermediate B-2, intermediate B-3 and final compound 6 were reacted in the same manner as in the synthesis method 2 to 4 of Synthesis Example 1 using Intermediate B-1, . ≪ / RTI >

Synthetic example  3: Synthesis of Compound 21

Compound 21 shown as a more specific example of the compound of the present invention was synthesized through the same route as Synthesis Example 1 above.

Step 1 : Synthesis of intermediate C-1

To a 1000 mL flask was added 10.0 g (36.75 mmol) of 2- (4-bromophenyl) indole, 9 g of (9 - ([ 1.1 eq of the acid, 2.2 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium, 200 mL of THF and 100 mL of water were added and stirred at 90 DEG C overnight.

After confirming the completion of the reaction by TLC and cooling, the organic layer was separated, and the solvent was removed under reduced pressure. 14.9 g (yield: 79%) of Intermediate C-1 was obtained through the column.

Intermediate C-2, intermediate C-3 and final compound 21 were reacted in the same manner as in the synthesis method 2 to 4 of Synthesis Example 1, using 69%, 84% and 78% of the intermediate C- . ≪ / RTI >

Synthetic example  4: Synthesis of Compound 49

Compound 49 shown as a more specific example of the compound of the present invention was synthesized through the route of the following 5 steps.

Step 1 : Synthesis of Intermediate D-1

To a 250 mL flask was added 10.0 g (51.75 mmol) of 2-phenylindole, 1.2 eq of iodobenzene, 0.03 eq of tris (dibenzylideneacetone) dipalladium, 0.15 eq of tetrabutylphosphine, 1.5 eq of sodium dodecylisobutoxide, And stirred at 110 ° C overnight. After confirming the completion of the reaction by TLC and cooling, the organic layer was separated and the solvent was removed under reduced pressure, and 11.3 g (yield: 81%) of Intermediate D-1 was obtained through the column.

Step 2 : Synthesis of intermediate D-2

10.0 g (37.13 mmol) of Intermediate D-1, 1 eq of NBS and 300 mL of tetrahydrofuran were added to a 1000 mL flask and stirred. After the completion of the reaction was confirmed by TLC, the solvent was removed under reduced pressure, and 6.3 g (yield: 49%) of Intermediate D-2 was obtained through the column.

Step 3 : Synthesis of intermediate D-3

4-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) (10.0 g, 22.45 mmol), 0.95 eq of 1-bromo-4-chlorobenzene, 2.0 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium, Lt; 0 > C overnight.

After confirming the completion of the reaction by TLC and cooling, the organic layer was separated, and the solvent was removed under reduced pressure. Then, 5.9 g (yield: 61%) of Intermediate D-3 was obtained through the column.

Step 4 : Synthesis of intermediate product (D-4)

To a 500 mL flask was added 10.0 g (22.45 mmol) of Intermediate D-3, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- 0.04 eq of [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II), 3.0 eq of potassium acetate and 100 mL of DMF were stirred at 150 ° C. overnight.

After confirming the completion of the reaction by TLC, the reaction mixture was cooled and the organic layer was separated. The solvent was removed under reduced pressure, and 7.6 g (yield: 63%) of Intermediate D-4 was obtained through the column.

Step 5: Synthesis of Compound 49

To a 500 mL flask was added 10.0 g (28.72 mmol) of Intermediate D-2, 1.1 eq of Intermediate D-4, 2.2 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium, 200 mL of THF, ≪ / RTI >

After confirming the completion of the reaction by TLC and cooling, the organic layer was separated, and the solvent was removed under reduced pressure. 14.6 g (yield: 77%) of Compound 49 was obtained through the column.

Synthetic example  5: Synthesis of Compound 69

Compound 69 shown as a more specific example of the compound of the present invention was synthesized through the same route as in Synthesis Example 4 above using Intermediate E-3 synthesized below instead of Intermediate D-3.

Step 3 : Synthesis of intermediate E-3

To a 500 mL flask was added 9- (4-phenylquinazolin-2-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 0.95 eq of 1-bromo-4-chlorobenzene, 2.0 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium, 200 mL of THF, and 100 mL of water were placed, Lt; / RTI >

After confirming the completion of the reaction by TLC, the reaction mixture was cooled and the organic layer was separated. The solvent was removed under reduced pressure, and 5.5 g (yield: 57%) of Intermediate E-3 was obtained through the column.

Intermediate E-4 and final compound 69 were obtained in a yield of 76% and 63%, respectively, by using the intermediate E-3 obtained above in the same manner as in the synthesis method of Synthesis Example 4, Step 4 and Step 5.

Synthetic example  6: Synthesis of Compound 71

Compound 71 shown as a more specific example of the compound of the present invention was synthesized through the same route as in Synthesis Example 4 above using Intermediate F-3 synthesized below in place of Intermediate D-3.

Step 3 : Synthesis of Intermediate F-3

A 500 mL flask was charged with 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxabolo 2-yl) -9H-carbazole, 0.95 eq of 1-bromo-4-chlorobenzene, 2.0 eq of potassium carbonate, 0.05 eq of tetrakis (triphenylphosphine) palladium and 200 mL of THF , And 100 ml of water, and the mixture was stirred at 90 캜 for overnight.

After confirming the completion of the reaction by TLC, the reaction mixture was cooled and the organic layer was separated. The solvent was removed under reduced pressure, and 6.8 g (yield: 70%) of Intermediate F-3 was obtained through the column.

Intermediate F-4 and final compound 71 were obtained in a yield of 73% and 88%, respectively, by using the intermediate F-3 produced above in the same manner as in the synthesis method of Step 4 and Step 5 of Preparation Example 4, respectively.

 (Fabrication of organic light emitting device)

Example  One

Compound 3 obtained in Synthesis Example 1 was used as a host and Ir (PPy) ₃ was used as a dopant to prepare an organic light emitting device.

As the anode, ITO was used in a thickness of 1000 Å, and as a cathode, aluminum (Al) was used in a thickness of 1000 Å. Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance of 15 Ω / cm 2 is cut into a size of 50 mm × 50 mm × 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes, UV ozone cleaning was used for 30 minutes.

N4, N4'-di (naphthalen-1-yl) -N4 and N4'-diphenylbiphenyl-4,4'-diamine were added on the substrate at a vacuum degree of 650 × 10 ^-7 Pa and a deposition rate of 0.1 to 0.3 nm / (NPB) (80 nm) was deposited thereon to form a 800 Å hole transport layer. Subsequently, a light emitting layer having a thickness of 300 angstroms was formed using the compound 3 obtained in Synthesis Example 1 under the same vacuum deposition conditions. At this time, a phosphorescent dopant Ir (PPy) ₃ (Cas No. 94928-86-6) Respectively. At this time, the deposition rate of the phosphorescent dopant was controlled so that the phosphorescent dopant content was 10% by weight when the total amount of the light emitting layer was 100% by weight.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq ₃ was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 200 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic photoelectric device.

The structure of the organic photoelectric device was ITO / NPB (80 nm) / EML (compound 3 (90 wt%) + Ir (PPy) ₃ (10 wt%), 30 nm) / Balq (5 nm) / Alq ₃ nm) / LiF (1 nm) / Al (100 nm).

Example  2 to Example  4

Examples 2 and 3 were prepared in the same manner as in Example 1, except that the compound 6 of Synthesis Example 2, the compound 21 of Synthesis Example 3, and the compound 49 of Synthesis Example 4 were used in place of the Compound 3 of Synthesis Example 1, respectively. And the organic light emitting device of Example 4 were fabricated.

Comparative Example  1 and Comparative Example  2

The organic light emitting devices of Comparative Examples 1 and 2 were fabricated in the same manner as in Example 1, except that the compound represented by the formula (a) and the compound represented by the formula (b) were used in place of the compound (3)

[Formula a] [Formula b]

evaluation

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

No. compound The driving voltage (V) Color (EL color) Efficiency (cd / A) 90% lifetime (h) (@ 5000 cd / m ² ) Example 1 Compound 3 4.28 Green 58.5 188 Example 2 Compound 6 4.20 Green 59.3 180 Example 3 Compound 21 4.15 Green 60.1 174 Example 4 Compound 49 4.14 Green 60.4 195 Comparative Example 1 A 4.46 Green 57.7 8 Comparative Example 2 Formula b 4.35 Green 59.0 6

Referring to Table 1, the organic light emitting devices according to Examples 1 to 4 are superior to the organic light emitting devices according to Comparative Examples 1 and 2 in driving voltage, .

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

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

Claims (11)

A compound for an organic optoelectronic device represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
L is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹ to R ⁹ each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C40 silyl group, a substituted or unsubstituted C6 to C30 aryl group, Lt; / RTI >
Each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted carbazolyl group,
Means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C4 alkyl group, or a C6 to C18 aryl group. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by the following Formula 1-I or 1-II:
[Chemical Formula 1-I] [Chemical Formula 1-II]

In the above general formulas (I-1) and (II-II)
L is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹ to R ⁹ each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C40 silyl group, a substituted or unsubstituted C6 to C30 aryl group, Lt; / RTI >
Ar ¹ to Ar ³ each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, but a substituted or unsubstituted carbazolyl group is excluded. The method according to claim 1,
Wherein L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, An unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted pyridylenyl group. The method according to claim 1,
Wherein L is one of the linking groups listed in the following Group < RTI ID = 0.0 > I: < / RTI &
[Group I]

In the above group I, * is a connection point with a neighboring atom. The method according to claim 1,
Each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, A substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted Or an unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinolinyl group. The method according to claim 1,
Wherein Ar ¹ to Ar ³ are each independently selected from the substituents listed in the following Group II:
[Group II]

In the above group II, * is a connection point with a neighboring atom. The method according to claim 1,
L is a para-phenylene group or a meta-phenylene group,
Each of R ¹ to R ⁹ is independently hydrogen or a phenyl group,
Each of Ar ¹ to Ar ³ independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrimidyl group A substituted or unsubstituted thiazolyl group, or a substituted or unsubstituted quinazolinyl group. The method according to claim 1,
A compound for an organic optoelectronic device, which is one of the compounds listed in the following Group 1:
[Group 1]
[1] [2] [3] [4]

[5] [6] [7] [8]

[9] [10] [11] [12]

[13] [14] [15] [16]

[17] 18 [19] [20]

[21] 22 [23] [24]

[25] 26 [27] [28]

[29] [30] [31] [32]

[33] [34] [35] [36]

[37] 38 [39] [40]

[41] [42] [43] [44]

[45] 46 [47] [48]

[49] 50 [51] [52]

[53] [54] 55 [56]

[57] 58 [59] [60]

[61] 62 [63] [64]

[65] 66 [67] [68]

[69] 70 [71] [72]

. Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
The organic optoelectronic device according to any one of claims 1 to 8, wherein the organic layer comprises a compound for an organic optoelectronic device. 10. The method of claim 9,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound for an organic optoelectronic device. A display device comprising the organic opto-electronic device according to claim 9.

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