Compound for organic optoelectronic device, organic optoelectronic device and display device

Abstract

The present invention relates to a compound for an organic photoelectric device represented by Chemical Formula 1, and an organic photoelectric device and a display device comprising the compound. The description of Chemical Formula 1 is the same as defined in the specification.

Description

Technical Field

[0001] Disclosed are a compound for an organic photoelectric device, an organic photoelectric device and a display device. Background Art

[0002] Organic optoelectronic devices (organic photodiodes) are devices that convert electrical energy into light energy and vice versa.

[0003] Organic photoelectric devices can be classified according to their driving principles as follows: one is a photoelectric device in which excitons generated by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes and generate electrical energy, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of the organic optoelectronic device include an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photoconductor.

[0005] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel displays. An organic light emitting diode is a device that converts electrical energy into light, and the performance of an organic light emitting diode is largely affected by an organic material disposed between electrodes. Summary of the invention

[0006] Technical issues

[0007] One embodiment provides a compound for an organic photoelectric device capable of realizing an organic photoelectric device having high efficiency and a long lifespan.

[0008] Another embodiment provides an organic photoelectric device including the compound for an organic photoelectric device.

[0009] Yet another embodiment provides a display device including the organic photoelectric device.

[0010] Technical Solution

[0011] According to one embodiment, a compound for an organic photoelectric device represented by Chemical Formula 1 is provided.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] R 1 is a C6 to C20 aryl group which may be substituted by a C1 to C5 alkyl group or a C6 to C12 aryl group or an unsubstituted C6 to C20 aryl group, a dibenzofuranyl group which may be substituted by a C6 to C12 aryl group or an unsubstituted dibenzothiophenyl group which may be substituted by a C6 to C12 aryl group or an unsubstituted dibenzofuranyl group,

[0016] R 2 To R 9 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0017] Ar 1 and Ar 2 Each is independently hydrogen, deuterium or C6 to C20 aryl.

[0018] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the above-mentioned compound for an organic photoelectric device.

[0019] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0020] Beneficial Effects

[0021] Organic optoelectronic devices with high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 and 2 is a cross-sectional view showing an organic light emitting diode according to each embodiment.

[0023] <Description of symbols>

[0024] 100, 200: Organic light-emitting diodes

[0025] 105: Organic layer

[0026] 110: cathode

[0027] 120: Anode

[0028] 130: Luminous layer

[0029] 140: Hole auxiliary layer DETAILED DESCRIPTION

[0030] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0031] In the present specification, when no definition is otherwise provided, "substituted" means that at least one hydrogen of the substituent or the compound is substituted with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0032] In one example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is replaced by deuterium, C1 to C5 alkyl, or C6 to C12 aryl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is replaced by methyl, ethyl, phenyl, biphenyl, or naphthyl.

[0033] In the present specification, when a definition is not otherwise provided, "hetero" means a group containing one to three hetero atoms selected from N, O, S, P and Si in one functional group and the rest being carbon.

[0034] In the present specification, "aryl group" means a group containing at least one hydrocarbon aromatic part, and may include a group in which all elements of the hydrocarbon aromatic part have p-orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic parts can be linked by a σ bond, such as biphenyl, terphenyl, tetraphenyl, etc., and a group in which two or more hydrocarbon aromatic parts are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0035] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0036] In this specification, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si instead of carbon (C) in a cyclic compound, such as aryl, cycloalkyl, condensed rings thereof or combinations thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0037] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryl groups are directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0038] More specifically, the substituted or unsubstituted C6-C30 aryl 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 phenanthrenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0039] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl 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 dibenzothienyl group, or a combination thereof, but is not limited thereto.

[0040] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) level.

[0041] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied according to the lowest unoccupied molecular orbital (LUMO) level, and the electrons formed in the cathode are easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive property.

[0042] Hereinafter, a compound according to one embodiment is described.

[0043] A compound according to one embodiment is represented by Chemical Formula 1.

[0044] [Chemical formula 1]

[0045]

[0046] In Chemical Formula 1,

[0047] R 1 is a C6 to C20 aryl group which may be substituted by a C1 to C5 alkyl group or a C6 to C12 aryl group or an unsubstituted C6 to C20 aryl group, a dibenzofuranyl group which may be substituted by a C6 to C12 aryl group or an unsubstituted dibenzothiophenyl group which may be substituted by a C6 to C12 aryl group or an unsubstituted dibenzofuranyl group,

[0048] R 2 To R 9 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0049] Ar 1 and Ar 2 Each is independently hydrogen, deuterium or C6 to C20 aryl.

[0050] The compound represented by Chemical Formula 1 may have a structure in which one carbazole group is directly connected to triazine in the N-direction without a linking group and another carbazole group is also connected to triazine in the N-direction through a meta-phenylene group at the center of the triazine.

[0051] Since one carbazole group is directly connected to the triazine in the N direction, that is, at the 9-position, there is no linking group, the compound has a relatively deep LUMO energy level, which is beneficial for electron injection and transport.

[0052] Furthermore, since another carbazole group is attached to triazine in the N direction (i.e., at the 9-position) to break the π bond via the C-N bond, the electron cloud between HOMO-LUMO is clearly positioned as the hole-transporting part and the electron-transporting part, and the attachment of the carbazole group to triazine via the m-phenylene group can more effectively separate this positioning, thereby maximizing the lifetime enhancement effect.

[0053] In other words, in a device including the compound represented by Chemical Formula 1, more favorable characteristics for lifespan may be obtained due to favorable hole / electron injection and transport and efficient positioning of electron clouds to achieve a stable structure of electrons and holes.

[0054] In particular, the compound includes triazine as a central core to ensure rapid electron injection and mobility, thereby achieving charge balance with the carbazole portion having strong hole mobility and also greatly contributing to long life characteristics.

[0055] For example, R 1 It may be an unsubstituted or C6 to C12 aryl-substituted phenyl group, an unsubstituted or C6 to C12 aryl-substituted biphenyl group, an unsubstituted or C6 to C12 aryl-substituted fluorenyl group, an unsubstituted or C6 to C12 aryl-substituted dibenzofuranyl group, or an unsubstituted or C6 to C12 aryl-substituted dibenzothienyl group.

[0056] For example, R 1 The substituents may be selected from Group I.

[0057] [Group I]

[0058]

[0059] For example, R 2 To R 5 may each independently be hydrogen or a C6 to C12 aryl group,

[0060] R 6 To R 9 Each may independently be hydrogen or a C6 to C12 aryl group.

[0061] As a specific example, all R 2 To R 5 It can be hydrogen or R 2 To R 5 Any one of them can be phenyl, and all R 6 To R 9 It can be hydrogen or R 6 To R 9 Any one of the may be phenyl.

[0062] For example, Ar 1 and Ar 2 Each may independently be hydrogen or a C6 to C12 aryl group.

[0063] As a specific example, Ar 1 and Ar 2 Each may independently be hydrogen, phenyl or biphenyl.

[0064] For example, Ar 1and Ar 2 Each may be hydrogen.

[0065] In the most specific embodiment, the compound for an organic photoelectric device represented by Chemical Formula 1 may be one of the compounds selected from Group 1, but is not limited thereto.

[0066] [Group 1]

[0067]

[0068]

[0069] In addition to the above-mentioned compounds for organic photoelectric devices, one or more compounds may be included.

[0070] For example, a dopant may be further included.

[0071] The dopant may be a phosphorescent dopant, such as a red or green phosphorescent dopant, and may be, for example, a green phosphorescent dopant.

[0072] The dopant is a material mixed in a small amount with a compound used for an organic photoelectric device to cause light emission, and generally can be a material such as a metal complex that emits light by multiple excitations to a triplet state or a multiplet state. The dopant can be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof can be used.

[0073] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal compound of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0074] [Chemical formula Z]

[0075] L 5 MX a

[0076] In the chemical formula Z, M is a metal and L 5 and X a They are the same as or different from each other and are ligands that form a complex compound with M.

[0077] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 5 and X a It may be, for example, a bidentate ligand.

[0078] The above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device may be used in a dry film formation method such as chemical vapor deposition (CVD).

[0079] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device is described.

[0080] The organic photoelectric device may be any device that converts electrical energy into light energy and vice versa without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photoconductor.

[0081] Herein, an organic light emitting diode as an example of an organic photoelectric device is described with reference to the accompanying drawings.

[0082] Figure 1 and 2 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0083] refer to Figure 1 , an organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0084] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0085] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0086] The organic layer 105 may include the above-mentioned compound used for an organic photoelectric device.

[0087] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-mentioned compound for an organic photoelectric device.

[0088] The composition for an organic photoelectric device further including a dopant may be, for example, a green light emitting composition.

[0089] The light emitting layer 130 may include, for example, the above-mentioned compound for organic optoelectronic devices as a phosphorescent host.

[0090] The organic layer may further include an auxiliary layer in addition to the light emitting layer.

[0091] The auxiliary layer may be, for example, a hole auxiliary layer 140 .

[0092] refer to Figure 1 In addition to the light emitting layer 130 , the organic light emitting diode 200 further includes a hole auxiliary layer 140 . The hole auxiliary layer 140 may further increase hole injection and / or hole mobility, and block electrons between the anode 120 and the light emitting layer 130 .

[0093] The hole auxiliary layer 140 may include, for example, at least one of the compounds of the D group.

[0094] 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 compounds of group D may be included in the hole transport auxiliary layer.

[0095] [Group D]

[0096]

[0097]

[0098]

[0099] In addition to the above compounds, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds having similar structures may be used for the hole transport auxiliary layer.

[0100] In addition, in the embodiment of the present invention, the organic light emitting diode may further include an electron transport layer, an electron injection layer and a hole injection layer as Figure 1 Or the organic layer 105 in 2.

[0101] The organic light emitting diodes 100 and 200 may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer by a dry film method such as evaporation, sputtering, plasma plating, and ion plating, and forming the cathode or the anode thereon.

[0102] The organic light emitting diode may be applied to an organic light emitting display device.

[0103] Hereinafter, the embodiments will be illustrated in more detail with reference to Examples. However, these Examples are exemplary, and the present scope is not limited thereto.

[0104] Hereinafter, unless otherwise described, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry or P&H tech, or synthesized by known methods.

[0105] (Preparation of compounds for organic optoelectronic devices)

[0106] A compound which is a more specific example of the compound of the present invention is synthesized by the following steps.

[0107] (Preparation of a First Compound for Organic Photoelectric Device)

[0108] Synthesis Example 1: Synthesis of Compound 2

[0109]

[0110] Step 1: Synthesis of Intermediate A

[0111] 65.5 g (216.79 mmol) of 2-[1,1'-biphenyl]-4-yl-4,6-dichloro-1,3,5-triazine and 25 g (149.51 mmol) of carbazole were suspended in 800 ml of THF, and then 15.09 g (156.99 mmol) of NaO(t-Bu) was slowly added thereto. The resulting mixture was stirred at room temperature for 12 hours, and the solid therein was filtered and washed with distilled water, acetone, and hexane to obtain 40.15 g (yield: 62%) of intermediate A.

[0112] Step 2: Synthesis of compound 2

[0113] 10 g (23.10 mmol) of intermediate A, 8.70 g (23.56 mmol) of 3-(9H-carbazole-9-yl)phenylboronic acid, 0.8 g (0.69 mmol) of Pd(PPh3)4 and 6.39 g (46.2 mmol) of K2CO3 were suspended in 100 ml of THF and 50 ml of distilled water, then refluxed and stirred for 12 hours. When the reaction was complete, the resultant was cooled to room temperature, the solid produced therein was filtered, and then washed with distilled water and acetone. The solid was then heated and dissolved in 200 ml of dichlorobenzene, filtered with silica gel, and recrystallized in 150 ml of dichlorobenzene to obtain 11 g (yield: 74%) of compound 2.

[0114] (LC / MS: theoretical value 639.75, found value: 640.40)

[0115] Synthesis Example 2: Synthesis of Compound 7

[0116]

[0117] Step 1: Synthesis of Intermediate B

[0118] 15 g (yield: 54%) of Intermediate B was obtained according to the same method as in the first step of Synthesis Example 1, except that 30 g (94.89 mmol) of 2,4-dichloro-6-(3-dibenzofuranyl)-1,3,5-triazine was used.

[0119] Step 2: Synthesis of compound 7

[0120] 10 g (yield: 68.4%) of Compound 7 was obtained according to the same method as in the second step of Synthesis Example 1, except that 10 g (22.38 mmol) of Intermediate B was added thereto.

[0121] (LC / MS: theoretical value 653.73, found value: 654.60)

[0122] Synthesis Example 3: Synthesis of Comparative Compound R1

[0123]

[0124] Step 1: Synthesis of Intermediate C

[0125] 30.29 g (105 mmol) of 3-(9H-carbazole-9-yl)phenylboronic acid, 20 g (105 mmol) of 1-bromo-4-chlorobenzene, 0.03 equivalent of Pd(PPh3)4 and 2 equivalents of K2CO3 were suspended in THF and distilled water, and then stirred for 12 hours. When the reaction was completed, the resultant was extracted, the organic layer thereof was concentrated, and silica gel was used to pass through a column to obtain 35 g (yield: 94%) of intermediate C.

[0126] Step 2: Synthesis of Intermediate D

[0127] 35 g (100 mmol) of Intermediate C, 4.85 g (10 mmol) of Pd(dppf)Cl2, 29.12 g (300 mmol) of KOAc, 30.14 g (120 mmol) of bis(pinacolato)diboron, and 6.66 g (20 mmol) of P(Cy)3 were suspended in 500 ml of DMF, and then refluxed and stirred for 12 hours. When the reaction was completed, distilled water was added to the reaction solution, the mixture was extracted / concentrated with dichloromethane, and passed through a silica gel column to obtain 30.8 g (yield: 70%) of Intermediate D.

[0128] Step 3: Synthesis of Comparative Compound R1

[0129] 5.0 g (11.23 mmol) of intermediate D, 3 g (11.23 mmol) of 2-chloro-4,6-diphenyltriazine, 0.03 equivalent of Pd(PPh3)4 and 2 equivalents of K2CO3 were suspended in THF and distilled water, then refluxed and stirred for 12 hours. When the reaction was complete, the solid produced therein was filtered and washed with distilled water and acetone. The solid was recrystallized from monochlorobenzene to obtain 4 g (yield: 65%) of comparative compound R1.

[0130] (LC / MS: theoretical value 550.65, found value: 551.4)

[0131] Synthesis Example 4: Synthesis of Comparative Compound R2

[0132]

[0133] Step 1: Synthesis of Intermediate F

[0134] 10 g (54.23 mmol) of cyanuric chloride and 18.13 g (108.45 mmol) of carbazole were suspended in 250 ml of THF, 7.81 g (81.35 mmol) of NaO (t-Bu) was slowly added thereto, and then stirred for 12 hours. When the reaction was completed, the solid produced therein was filtered, washed with distilled water and acetone / hexane, and 12 g (yield: 49.6%) of intermediate F was obtained as the target compound.

[0135] Step 2: Synthesis of Comparative Compound R2

[0136] 6 g (13.46 mmol) of intermediate F, 5.13 g (14.13 mmol) of 4-(9H-carbazole-9-yl) biphenylboronic acid, 0.47 g (0.40 mmol) of Pd(PPh3)4 and 3.72 g (26.91 mmol) of K2CO3 were suspended in 100 ml of THF and 50 ml of distilled water, then refluxed and stirred for 12 hours. When the reaction was complete, the solid produced therein was filtered and washed with distilled water / acetone. The obtained solid was heated and dissolved in 300 ml of dichlorobenzene, then filtered with silica gel, the filtrate therein was cooled to room temperature, the solid produced therein was filtered and dried, and 3.9 g (yield: 40%) of comparative compound R2 was obtained as the target compound.

[0137] (LC / MS: theoretical value 728.84, found value: 729.6)

[0138] Synthesis Example 5: Synthesis of Comparative Compound R3

[0139]

[0140] Step 1: Synthesis of Intermediate G

[0141] 36.9 g (200 mmol) of cyanuric chloride and 33.4 g (200 mmol) of carbazole were suspended in 300 ml of THF, and 19.22 g (200 mmol) of NaO(t-Bu) were slowly added thereto at ℃. When the reaction was completed, the solid produced therein was filtered and washed with distilled water / acetone / hexane to obtain 10 g (yield: 16%) of intermediate G.

[0142] Step 2: Synthesis of Intermediate H

[0143] 4.9 g (15.55 mmol) of intermediate G, 6.69 g (15.55 mmol) of intermediate I (see Synthesis Example 3 of Korean Patent Publication No. 10-2014-0135524), 0.89 g (0.78 mmol) of Pd (PPh 3) 4 and 5.37 g (38.87 mmol) of K 2 CO 3 were suspended in 50 ml of THF / 50 ml of toluene / 50 ml of distilled water, and then refluxed and stirred. When the reaction was completed, the solid produced was filtered, washed with distilled water / acetone, and dried to obtain 5 g (yield: 56%) of intermediate H.

[0144] Step 3: Synthesis of Comparative Compound R3

[0145] 2.4 g (4.11 mmol) of intermediate H, 1.67 g (4.53 mmol) of 9-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-9H-carbazole, 0.14 g (0.12 mmol) of Pd(PPh3)3 and 1.14 g (8.23 mmol) of K2CO3 were suspended in 50 ml of THF and 50 ml of DIW, and then refluxed and stirred for 12 hours. When the reaction was completed, the solid produced therein was filtered and washed with distilled water and acetone. The solid was heated and dissolved in 100 ml of dichlorobenzene, filtered with silica gel, and the filtrate therein was cooled to room temperature. The solid produced in the filtrate was filtered and washed with acetone to obtain 2.94 g (yield: 89.5%) of comparative compound R3.

[0146] (LC / MS: theoretical value 789.92, found value: 790.40)

[0147] Synthesis Example 6: Synthesis of Comparative Compound R4

[0148]

[0149]

[0150] Step 1: Synthesis of Intermediate J

[0151] 30g (123.30mmol) of 3-phenyl-9H-carbazole, 30.69g (160.30mmol) of 1-bromo-4-chlorobenzene, 4.70g (24.66mmol) of CuI, 51.13g (369.91mmol) of K2CO3 and 4.44g (24.66mmol) of 1,10-phenanthroline were suspended in 300ml of DMF, then refluxed and stirred for 12 hours. At the end of the reaction, the resultant was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and concentrated with toluene. The product was passed through a silica gel column to obtain 21g (yield: 48%) of intermediate J.

[0152] Step 2: Synthesis of Intermediate K

[0153] 10.6 g (yield: 39%) of Compound K was synthesized according to the same method as in the second step of Synthesis Example 3, except that 21 g (59.35 mmol) of Intermediate J was used.

[0154] Step 3: Synthesis of Intermediate L

[0155] 58.81 g (260.15 mmol) of 2-phenyl-4,6-dichlorotriazine and 30 g (179.42 mmol) of carbazole were suspended in 500 ml of THF, and then 18.11 g of NaO (t-Bu) was slowly added thereto, followed by stirring at room temperature for 12 hours. When the reaction was completed, the solid produced therein was filtered, washed with distilled water and acetone, and dried to obtain 40 g (yield: 62.5%) of intermediate L.

[0156] Step 4: Synthesis of Comparative Compound R4

[0157] 8 g (yield: 53.5%) of Comparative Compound R4 was obtained according to the same method as in the second step of Synthesis Example 1, except that 8.34 g (23.37 mmol) of Intermediate L and 10.62 g (23.84 mmol) of Intermediate K were used.

[0158] (LC / MS: theoretical value 639.75, found value: 640.52)

[0159] (Preparation of a Second Compound for Organic Photoelectric Device)

[0160] Synthesis Example 7: Synthesis of Compound B-99

[0161] Compound B-99 was synthesized in the same manner as known in US2017-0317293A1.

[0162] Synthesis Example 8: Synthesis of Compound C-4

[0163]

[0164] C-4

[0165] 8g (31.2mmol) of 5,8-dihydroindole [2,3-c] carbazole (CAS No.: 200339-30-6), 20.5g (73.32mmol) of 4-iodobiphenyl, 1.19g (6.24mmol) of CuI, 1.12g (6.24mmol) of 1,10-phenanthroline and 12.9g (93.23mmol) of K2CO3 were placed in a round-bottom flask, 50ml of DMF was added thereto, and then refluxed and stirred for 24 hours under a nitrogen atmosphere. At the end of the reaction, distilled water was added thereto to precipitate a solid, and the solid was filtered. The solid was dissolved in 250ml of xylene, filtered using silica gel, and precipitated as a white solid to obtain 16.2g (yield: 93%) of compound C-4.

[0166] LC / MS calculated value C42H28N2 exact mass: 560.2252 found value: 561.23

[0167] (Manufacturing of organic light-emitting diodes)

[0168] Example 1

[0169] Wash with distilled water After washing with distilled water, the glass substrate is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The obtained ITO transparent electrode is used as an anode, and compound A is vacuum deposited on the ITO substrate to form The compound B is deposited on the injection layer to form a hole injection layer. Thickness, then compound C is deposited to On the hole transport layer, the compound 2 prepared in Example 1 was used as a host and doped with 7 wt % of PtGD as a dopant by vacuum deposition to form a hole transport layer. Subsequently, on the light-emitting layer, compound D and Liq were simultaneously vacuum deposited in a ratio of 1:1 to form A thick electron transport layer is formed, and on the electron transport layer, Liq and Al are vacuum-deposited in sequence. Thick and harmonious Thick, making organic light emitting diodes.

[0170] The organic light emitting diode has multiple organic thin layers, and specifically has the following structure.

[0171] ITO / Compound A / Compound B / Compound C / EML[Compound 2: PhGD (7 wt%)] / Compound D: Liq / Liq / aluminum

[0172] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)biphenyl-4,4'-diamine

[0173] Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexanitrile (HAT-CN),

[0174] Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0175] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinoline

[0176] Examples 2 to 11 and Comparative Examples 1 to 6

[0177] The diodes of Examples 2 to 11 and Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the bodies were changed as described in Tables 1 to 6.

[0178] Evaluation: Effect of prolonging life

[0179] The driving voltage and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 11 and Comparative Examples 1 to 6 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 1 to 6.

[0180] (1) Life measurement

[0181] At 24000cd / m 2 As the initial brightness (cd / m 2 ) emits light and uses the Polanonix lifetime measurement system to measure the decrease in brightness over time. When its brightness is relative to the initial brightness (cd / m 2 ) is reduced to 90%, the T90 lifetimes of the organic light emitting diodes according to Examples 1 to 11 and Comparative Examples 1 to 6 are measured as a function of time.

[0182] (2) Calculation of T90 life ratio (%)

[0183] Relative comparison values ​​of T90(h) for single host or mixed host examples (using the first compound as the first host) and mixed host comparative examples (using the comparative compound as the first host) using the same second host are shown.

[0184] T90 life ratio (%) = {[T90(h) of Example (first compound used as a single or mixed host) / [T90(h) of Comparative Example (comparative compound used as a single or mixed host)]}×100

[0185] [Table 1]

[0186] main body T90 life ratio (%) Example 1 Compound 2 200％ Example 2 Compound 7 195％ Comparative Example 1 Comparative Compound R1 100％

[0187] [Table 2]

[0188] main body T90 life ratio (%) Example 3 Compound 2 400％ Example 4 Compound 7 380％ Comparative Example 2 Comparative Compound R2 100％

[0189] [Table 3]

[0190] main body T90 life ratio (%) Example 5 Compound 2 210％ Example 6 Compound 7 194％ Comparative Example 3 Comparative Compound R3 100％

[0191] [Table 4]

[0192] main body T90 life ratio (%) Example 7 Compound 2 130％ Example 8 Compound 7 129％ Comparative Example 4 Comparative Compound R4 100％

[0193] [Table 5]

[0194]

[0195] [Table 6]

[0196]

[0197] Referring to Tables 1 to 6, the lifespans of the organic light emitting diodes according to Examples 1 to 11 are significantly improved compared to the organic light emitting diodes according to Comparative Examples 1 to 6.

[0198] While the invention has been described in connection with what are presently considered to be practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device represented by Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, R 1 Substituents selected from Group I: [Group I] Where, in Group I, * is the connection point, R 2 To R 5 are each independently hydrogen or deuterium, R 6 To R 9 are each independently hydrogen, deuterium, cyano or halogen, and Ar 1 and Ar 2 are each independently hydrogen or deuterium.

2. The compound according to claim 1, wherein R 6 To R 9 are each independently hydrogen.

3. The compound according to claim 1, wherein Ar 1 and Ar 2 are each independently hydrogen.

4. A compound which is one of the compounds of Group 1: [Group 1] 5. An organic optoelectronic device, comprising: The anode and cathode face each other, at least one organic layer disposed between the anode and the cathode, The organic layer comprises the compound for an organic photoelectric device according to any one of claims 1 to 4.

6. The organic optoelectronic device according to claim 5, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device.

7. A display device comprising the organic photoelectric device according to claim 5.

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