KR20210129497A - Compound for organic optoelectronic device, organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectronic device represented by chemical formula 1, and an organic optoelectronic device, and a display apparatus including the same. Details of the chemical formula 1 are as defined in the specification. According to one embodiment, provided is the compound for the organic optoelectronic device represented by chemical formula 1. The present invention can realize a high-efficiency, long-life organic optoelectronic device.

Description

Compounds for organic optoelectronic devices, organic optoelectronic devices, and display devices

It relates to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device.

An organic optoelectronic diode is a device capable of converting electrical energy and optical energy.

Organic optoelectronic devices can be roughly divided into two types according to their operating principles. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes and electrons and holes are transferred to different electrodes, and the other is electrical energy by supplying voltage or current to the electrode. It is a light emitting device that generates light energy from

Examples of the organic optoelectronic device may include an organic optoelectronic device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.

Among them, organic light emitting diodes (OLEDs) have recently attracted much attention due to an increase in demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by an organic material positioned between electrodes.

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

Another embodiment provides an organic optoelectronic device including the compound.

Another embodiment provides a display device including the organic optoelectronic device.

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

[Formula 1]

In Formula 1,

R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

At least one of R ¹ to R ⁷ is a group represented by the following formula (a),

[Formula a]

In the above formula (a),

L ¹ is a substituted or unsubstituted C6 to C20 arylene group,

L ² and L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

R ⁸ and R ⁹ are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

* is the connection point.

According to another embodiment, there is provided an organic optoelectronic 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 includes the compound for an organic optoelectronic device.

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

A high-efficiency, long-life organic optoelectronic device can be realized.

1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an exemplary embodiment, respectively.

Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

As used herein, unless otherwise defined, at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group means it has been

As used herein, "hetero" means that, unless otherwise defined, one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon. .

As used herein, the term "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated. It contains a form that forms, for example, a phenyl group, a naphthyl group, etc., and includes a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and two or more hydrocarbon aromatic moieties They may include a non-aromatic fused ring fused directly or indirectly, such as a fluorenyl group, and the like.

Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

In the present specification, "heterocyclic group" is a higher concept including a heteroaryl group, and instead of carbon (C), N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may include one or more heteroatoms.

For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

More specifically, a substituted or unsubstituted C6 to C30 aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted It may be a cyclic furanyl group, or a combination thereof, but is not limited thereto.

More specifically, a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, A substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted 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, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazine A diyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene It may be a diary, or a combination thereof, but is not limited thereto.

As used herein, the hole property refers to a property capable of forming a hole by donating electrons when an electric field is applied. It refers to a property that facilitates the movement of holes formed in the anode and in the light emitting layer.

In addition, the electronic property refers to a property that can receive electrons when an electric field is applied. It has conduction properties along the LUMO level, so electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer are moved to the cathode, and in the light emitting layer. properties that facilitate movement.

Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

The compound for an organic optoelectronic device according to an embodiment is represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1,

R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

At least one of R ¹ to R ⁷ is a group represented by the following formula (a),

[Formula a]

In the above formula (a),

L ¹ is a substituted or unsubstituted C6 to C20 arylene group,

L ² and L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

R ⁸ and R ⁹ are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

* is the connection point.

The compound represented by Formula 1 has a core in which phenyl is further fused to indolocarbazole, and a structure in which at least one substituted or unsubstituted triazine group is substituted in the core.

Indolocarbazole had a problem that it could not have sufficient hole mobility due to the deep HOMO energy level, but the present invention made it possible to have a shallow HOMO level by further fusion of indolocarbazole. Accordingly, it was possible to secure a fast hole transport capability. By substituting a triazine group here, the driving voltage, luminous efficiency, and lifespan characteristics of a device to which it is applied can be improved by balancing the charge of holes and electrons.

In particular, the triazine group substituted on the core may have T1 energy suitable for application as a host by being connected through a substituted or unsubstituted arylene, and this T1 energy value may have when the triazine group is directly substituted. It can be confirmed through a comparative example to be described later.

According to the substitution position of the substituent represented by Formula (a), Formula 1 may be, for example, represented by any one of Formulas 1A to 1C below.

[Formula 1A] [Formula 1B]

[Formula 1C]

In Formula 1A to Formula 1C,

R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ⁸ , R ⁹ , and L ¹ to L ³ are the same as described above.

As a more specific example, depending on the connection point of the substituent represented by Formula (a), it may be represented by, for example, any one of Formulas 1A-1, 1A-2, 1B-1 to Formula 1B-4, and Formula 1C-1.

[Formula 1A-1] [Formula 1A-2]

[Formula 1B-1] [Formula 1B-2]

[Formula 1B-3] [Formula 1B-4]

[Formula 1C-1]

In Formula 1A-1, Formula 1B-1 to Formula 1B-4, and Formula 1C-1, R ¹ to R ⁹ , and L ¹ to L ³ are the same as described above.

In an embodiment, Formula 1 may be represented by any one of Formula 1A-1, Formula 1A-2, Formula 1B-1, Formula 1B-3, Formula 1B-4, and Formula 1C-1.

For example, Formula 1 may be represented by Formula 1A-1 or Formula 1A-2.

For example, L ¹ may be a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

As a specific example, L ¹ may be selected from the linking groups listed in Group I below.

[Group I]

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

For example, L ¹ may be ortho-phenylene, meta-phenylene, or para-phenylene.

For example, L ² and L ³ are each independently a single bond, or a substituted or unsubstituted phenylene group,

wherein R ⁸ and R ⁹ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzo It may be a thiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

In a specific example, *-L ² -R ⁸ and *-L ³ -R ⁹ may each independently be selected from the substituents listed in Group II below.

[Group II]

In group II above, * is a connection point.

For example, L ² and L ³ may each independently be a single bond or a phenylene group.

For example, R ⁸ and R ⁹ may each independently be a phenylene group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

For example, R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted triazinyl group, and ^{any one of R 1} to R ⁷ is represented by the above formula It may be a group represented by a.

In a specific example, R ¹ to R ⁷ may each independently be hydrogen, deuterium, or a substituted or unsubstituted triazinyl group, and ^{any one of R 1} to R ⁷ may be a group represented by Formula (a).

For example, the compound for an organic optoelectronic device represented by Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[Group 1]

In addition to the above-described compound for an organic optoelectronic device, one or more compounds may be further included.

For example, the compound for an organic optoelectronic device described above may be applied in the form of a composition further comprising a known host material.

For example, the compound for an organic optoelectronic device described above may further include a dopant.

The dopant may be, for example, a phosphorescent dopant, such as a phosphorescent dopant of red, green or blue, and may be, for example, a red phosphorescent dopant.

A dopant is a material that emits light by being mixed in a small amount in a compound or composition for an organic optoelectronic device, and a material such as a metal complex that emits light by multiple excitation that excites it to a triplet state or more is generally used. can The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more kinds.

Examples of the dopant include a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. and organometallic compounds containing them. The phosphorescent dopant may be, for example, a compound represented by the following Chemical Formula Z, but is not limited thereto.

[Formula Z]

L ⁴ MX

In Formula Z, M is a metal, and L ⁴ and X are the same as or different from each other and are ligands forming a complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and L ⁴ and X are, for example, Biden It may be a tate ligand.

The compound for an organic optoelectronic device described above may be formed by a dry film deposition method such as chemical vapor deposition.

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

The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and optical energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.

Herein, 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 diode according to an exemplary embodiment.

Referring to FIG. 1 , an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110 . include

The anode 120 may be made of, for example, a conductor having a high work function to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The anode 120 may include, for example, 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); combinations of metals and oxides such as ZnO and Al or SnO _{2 and Sb;} conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline, but are limited thereto it is not

The cathode 110 may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The negative electrode 110 may include, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; and a multilayer structure material such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca, but is not limited thereto.

The organic layer 105 may include the aforementioned compound for an organic optoelectronic device.

The organic layer 105 may include the emission layer 130 , and the emission layer 130 may include the aforementioned compound for an organic optoelectronic device.

The composition for an organic optoelectronic device further comprising a dopant may be, for example, a red light-emitting composition.

The emission layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

The organic layer may further include an auxiliary layer in addition to the emission layer.

The auxiliary layer may be, for example, the hole auxiliary layer 140 .

Referring to FIG. 2 , the organic light emitting device 200 further includes a hole auxiliary layer 140 in addition to the emission layer 130 . The hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the emission layer 130 and block electrons.

The hole auxiliary layer 140 may include, for example, at least one of the compounds listed in Group E below.

Specifically, the hole auxiliary layer 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer. At least one of the listed compounds may be included in the hole transport auxiliary layer.

[Group E]

In the hole transport auxiliary layer, in addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure may also be used.

In addition, in one embodiment of the present invention, as the organic layer 105 in FIG. 1 or FIG. 2 , it may be an organic light emitting device further including an electron transport layer, an electron injection layer, a hole injection layer, and the like.

After forming an anode or a cathode on a substrate, the organic light emitting devices 100 and 200 form an organic layer by a dry film deposition method such as vacuum deposition, sputtering, plasma plating and ion plating, etc. It can be manufactured by forming a negative electrode or an anode.

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

The above-described embodiment will be described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights.

Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo chemical industry, or P&H tech, or synthesized through a known method, unless otherwise specified.

(Production of compounds for organic optoelectronic devices)

The compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

Synthesis Example 1: Preparation of Compound 1

[Scheme 1]

a) Synthesis of Intermediate 1-1

In a round bottom flask, 28.24 g (110.19 mmol) of 11,12-dihydroindolo[2,3-a]carbazole, 17.00 g (121.2 mmol) of 4-chloro-1,2-difluorobenzene, and 53.85 g (165.28 mmol _{) of Cs 2} CO _{3 were added.} ) was dissolved in NMP 350 mL solvent, and then heated to reflux at 200 °C under nitrogen atmosphere. After 6 hours, the reaction solution is cooled, and water and methanol are added to form a precipitate. After obtaining a solid through a glass filter and washing with methanol, 38.0 g (95% yield) of Intermediate 1-1 was obtained.

b) synthesis of intermediate 1-2

In a round bottom flask, 20.0 g (54.82 mmol) of the synthesized intermediate 1-1 was placed in 200 mL of DMF, Pd(dppf)Cl ₂ 2.69 g (3.29 mmol), bispinacolato diboron 1.71 g (65.78 mmol), After tricyclohexylphosphine 3.69 (13.16 mmol) and potassium acetate 16.14 g (164.46 mmol) were added, the mixture was heated to reflux under nitrogen atmosphere for 12 hours. The reaction solution is cooled, and the solid is collected by dropping it into 2 L of water. The obtained solid is dissolved in boiling toluene, filtered through silica gel, and the filtrate is concentrated. After the concentrated solid was stirred with a small amount of hexane, the solid was filtered to obtain 20.0 g (80% yield) of Intermediate 1-2.

c) synthesis of compound 1

In a round bottom flask, 10.0 g (21.91 mmol) of Intermediate 1-2, 9.67 g (21.91 mmol) of 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine, tetrakistriphenylphosphine palladium 0.76 g (0.66 mmol), and 6.06 g (43.83 mmol) of potassium carbonate were added, dissolved in 100 mL of tetrahydrofuran and 50 mL of distilled water, and then heated to reflux under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. After washing the obtained solid with water and methanol, the solid was recrystallized with 200 mL of toluene to obtain 12.0 g (86% yield) of Compound 1.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.56 [M+H]

Synthesis Example 2: Preparation of compound 4

[Scheme 2]

Intermediate 1-2 and 2-(2-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine in the above synthesis example using 1.0 equivalent each Compound 4 was synthesized in the same manner as in c) of 1 .

LC/MS calculated for: C51H29N5O Exact Mass: 727.83 found for 727.72 [M+H]

Synthesis Example 3: Preparation of compound 8

[Scheme 3]

Intermediate 1-2 and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used in 1.0 equivalents, respectively, to synthesize compound 8 in the same manner as in c) of Synthesis Example 1 above.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.56 [M+H]

Synthesis Example 4: Preparation of compound 11

[Scheme 4]

a) Synthesis of intermediate 11-1

Intermediate 11-1 was synthesized in the same manner as in a) of Synthesis Example 1, using 1.0:1.1 equivalents of intermediate 11,12-dihydroindolo[2,3-a]carbazole and 1-chloro-2,3-difluorobenzene, respectively. did.

b) synthesis of intermediate 11-2

Intermediate 11-2 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0:1.1 equivalents of Intermediate 11-1 and Bispinacolato diboron, respectively.

c) synthesis of compound 11

Intermediate 11-2 and 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used in an amount of 1.0 equivalent, respectively, to synthesize compound 11 in the same manner as in c) of Synthesis Example 1 above.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.63 [M+H]

Synthesis Example 5: Preparation of compound 13

[Scheme 5]

Intermediate 11-2 and 2-(2-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine in the above synthesis example using 1.0 equivalent each Compound 13 was synthesized in the same manner as in c) of 1 .

LC/MS calculated for: C51H29N5O Exact Mass: 727.83 found for 727.72 [M+H]

Synthesis Example 6: Preparation of compound 22

[Scheme 6]

a) Synthesis of Intermediate 22-1

Intermediate 22-1 was synthesized in the same manner as in a) of Synthesis Example 1, using 1.0:1.1 equivalents of 1-chloro-11,12-dihydroindolo[2,3-a]carbazole and 1,2-difluorobenzene, respectively. .

b) synthesis of intermediate 22-2

Intermediate 22-2 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0:1.1 equivalents of Intermediate 22-1 and Bispinacolato diboron, respectively.

c) synthesis of compound 22

Intermediate 22-2 and 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used in 1.0 equivalents, respectively, to synthesize compound 22 in the same manner as in c) of Synthesis Example 1 above.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.67 [M+H]

Synthesis Example 7: Preparation of compound 30

[Scheme 7]

a) Synthesis of Intermediate 30-1

Intermediate 30-1 was synthesized in the same manner as in a) of Synthesis Example 1, using 1.0:1.1 equivalents of 4-chloro-11,12-dihydroindolo[2,3-a]carbazole and 1,2-difluorobenzene, respectively. .

b) Synthesis of Intermediate 30-2

Intermediate 30-2 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0:1.1 equivalents of Intermediate 30-1 and Bispinacolato diboron, respectively.

c) synthesis of compound 30

Intermediate 30-2 and 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used in an amount of 1.0 equivalent, respectively, to synthesize compound 30 in the same manner as in c) of Synthesis Example 1 above.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.45 [M+H]

Synthesis Example 8: Preparation of compound 33

[Scheme 8]

a) Synthesis of intermediate 33-1

Intermediate 33-1 was synthesized in the same manner as in a) of Synthesis Example 1 above using 5-bromo-11,12-dihydroindolo[2,3-a]carbazole and 1.0:1.1 equivalents of 1,2-difluorobenzene, respectively. .

b) synthesis of intermediate 33-2

Intermediate 33-2 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0:1.1 equivalents of Intermediate 33-1 and Bispinacolato diboron, respectively.

c) synthesis of compound 33

Intermediate 33-2 and 2-([1,1'-biphenyl]-4-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine were synthesized using 1.0 equivalents each Compound 33 was synthesized in the same manner as in Example 1 c).

LC/MS calculated for: C51H31N5 Exact Mass: 713.84 found for 713.75 [M+H]

Synthesis Example 9: Preparation of compound 27

[Scheme 9]

a) Synthesis of intermediate 27-1

Intermediate 27-1 was synthesized in the same manner as in a) of Synthesis Example 1 above using 1.0:1.1 equivalents of 3-chloro-11,12-dihydroindolo[2,3-a]carbazole and 1,2-difluorobenzene, respectively. .

b) Synthesis of intermediate 27-2

Intermediate 27-2 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0:1.1 equivalents of Intermediate 27-1 and Bispinacolato diboron, respectively.

c) synthesis of compound 27

Intermediate 27-2 and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used in 1.0 equivalents, respectively, to synthesize compound 27 in the same manner as in c) of Synthesis Example 1 above.

LC/MS calculated for: C45H27N5 Exact Mass: 637.75 found for 637.53 [M+H]

Comparative Synthesis Example 1: Synthesis of Compound A

[Scheme 10]

Compound A was synthesized in the same manner as in c) of Synthesis Example 1, using 1.0 equivalents of Intermediate 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine, respectively.

LC/MS calculated for: C39H23N5 Exact Mass: 561.65 found for 561.52 [M+H]

Comparative Synthesis Example 2: Synthesis of Compound B

[Scheme 11]

Compound B was synthesized in the same manner as in c) of Synthesis Example 1, using 1.0 equivalents of Intermediate 27-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine, respectively.

LC/MS calculated for: C39H23N5 Exact Mass: 561.65 found for 561.48 [M+H]

Comparative Synthesis Example 3: Synthesis of Compound C

[Scheme 12]

Intermediate 27-2 and 3-bromo-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole were each used in 1.0 equivalents, as in c) of Synthesis Example 1 above. Compound C was synthesized by the method.

LC/MS calculated for: C51H30N6 Exact Mass: 726.84 found for 726.74 [M+H]

(Production of organic light emitting device)

Example 1

A glass substrate coated with indium tin oxide (ITO) was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, and transferred to a plasma cleaner, and then the substrate was cleaned using oxygen plasma for 10 minutes and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, vacuum deposition of Compound D doped with 1% NDP-9 (commercially available from Novaled) on an ITO substrate to form a hole transport layer with a thickness of 1400 Å and a compound on the hole transport layer E was deposited to a thickness of 600 Å to form a hole transport auxiliary layer. Compound 1 was used as a host on the hole transport auxiliary layer _{and doped with [Ir(piq) 2} acac] 2wt% as a dopant to form an emission layer with a thickness of 400 Å by vacuum deposition. Then, compound F was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound G and LiQ were simultaneously vacuum-deposited at a 1:1 ratio to form an electron transport layer having a thickness of 300 Å. An organic light emitting device was manufactured by sequentially vacuum-depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer to form a cathode.

ITO / Compound D (1% NDP-9 doping, 1400Å) / Compound E (600Å) / EML [Compound 1: [Ir(piq) ₂ acac] (2wt%)] (400Å) / Compound F (50Å) / Compound G: Liq (300 Å) / LiQ (15 Å) / Al (1200 Å) was prepared in the structure.

Compound D: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Compound E: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amine

Compound F: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

Compound G: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

Examples 2 to 9, and Comparative Examples 1 to 3

Devices of Examples 2 to 9 and Comparative Examples 1 to 3 were manufactured in the same manner as in Example 1, except that the host was changed as shown in Table 1 below.

Evaluation: Confirmation of Life Enhancement Effect

(1) Measurement of change in current density according to voltage change

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

(2) Measurement of luminance change according to voltage change

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

(3) Measurement of luminous efficiency

Using the luminance and current density measured from (1) and (2) above, the luminous efficiency (cd/A) of ^{the same current density (10 mA/cm 2 ) was calculated.}

(4) Lifetime measurement

Maintaining the luminance (cd / m ²⁾ to 6,000cd / m ² and the light emitting efficiency (cd / A) to obtain a result by measuring the time to decrease to 90%.

(5) T90 life ratio (%) calculation

Based on the T90(h) lifespan value of Comparative Example 1, the relative comparative values for the T90(h) lifespan values of Examples 1 to 9, Comparative Examples 2 and 3 are shown in Table 1 below.

division sole host T90 Life Ratio (%) Comparative Example 1 A 100 Comparative Example 2 B 101 Comparative Example 3 C 98 Example 1 One 138 Example 2 4 140 Example 3 8 155 Example 4 11 150 Example 5 13 175 Example 6 22 127 Example 7 27 120 Example 8 30 122 Example 9 33 125

Referring to Table 1, it can be seen that the compound according to the present invention has significantly improved lifespan compared to the comparative compound.

Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention. will be.

100, 200: organic light emitting device
105: organic layer
110: cathode
120: positive electrode
130: light emitting layer
140: hole auxiliary layer

Claims (13)

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

In Formula 1,
R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
At least one of R ¹ to R ⁷ is a group represented by the following formula (a),
[Formula a]

In the above formula (a),
L ¹ is a substituted or unsubstituted C6 to C20 arylene group,
L ² and L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
R ⁸ and R ⁹ are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
* is the connection point. According to claim 1,
Formula 1 is a compound for an organic optoelectronic device represented by any one of Formula 1A to Formula 1C:
[Formula 1A] [Formula 1B]

[Formula 1C]

In Formula 1A to Formula 1C,
R ¹ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
The definitions of R ⁸ , R ⁹ , and L ¹ to L ³ are as described in claim 1. According to claim 1,
Formula 1 is a compound for an organic optoelectronic device represented by any one of Formula 1A-1, Formula 1A-2, Formula 1B-1 to Formula 1B-4, and Formula 1C-1:
[Formula 1A-1] [Formula 1A-2]

[Formula 1B-1] [Formula 1B-2]

[Formula 1B-3] [Formula 1B-4]

[Formula 1C-1]

In Formula 1A-1, Formula 1A-2, Formula 1B-1 to Formula 1B-4, and Formula 1C-1,
The definitions of R ¹ to R ⁹ , and L ¹ to L ³ are as described in claim 1. 4. The method of claim 3,
Formula 1 is a compound for an organic optoelectronic device represented by any one of Formula 1A-1, Formula 1A-2, Formula 1B-1, Formula 1B-3, Formula 1B-4, and Formula 1C-1. 4. The method of claim 3,
Formula 1 is a compound for an organic optoelectronic device represented by Formula 1A-1 or Formula 1A-2. According to claim 1,
Wherein L ¹ is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, a compound for an organic optoelectronic device. 7. The method of claim 6,
Wherein L ¹ is one selected from the linking groups listed in the following group I compound for an organic optoelectronic device:
[Group I]

In the above group I, * is a connection point. According to claim 1,
The L ² and L ³ are each independently a single bond, or a substituted or unsubstituted phenylene group,
wherein R ⁸ and R ⁹ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzo A thiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, a compound for an organic optoelectronic device. 9. The method of claim 8,
The *-L ² -R ⁸ and *-L ³ -R ⁹ are each independently one selected from the substituents listed in the following group II compound for an organic optoelectronic device:
[Group II]

In group II above, * is a connection point. According to claim 1,
A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1:
[Group 1]

. positive and negative poles facing each other,
At least one organic layer positioned between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device according to any one of claims 1 to 10. 12. The method of claim 11,
The organic layer includes a light emitting layer,
The light emitting layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device. A display device comprising the organic optoelectronic device according to claim 11 .

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