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

Abstract

Disclosed are a compound represented by Chemical Formula 1, a composition comprising the compound, an organic optoelectronic device, and a display device. The definition of Chemical Formula 1 is the same as that in the specification.

Description

Technical Field

[0001] The invention discloses a compound for an organic photoelectric device, a composition 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 photovoltaic device in which excitons are generated by light energy, separated into electrons and holes and transferred to different electrodes to generate electric energy, and the other is a light-emitting device in which voltage or current is supplied to electrodes to generate light energy from electric energy.

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

[0005] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. Organic light emitting diodes convert electrical energy into light, and organic materials disposed between electrodes greatly affect the performance of organic light emitting diodes. Summary of the invention

[0006] Technical issues

[0007] The embodiment provides a compound for an organic optoelectronic device capable of achieving a high efficiency and long life organic optoelectronic device.

[0008] Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

[0009] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0010] Another embodiment provides a display device including the organic optoelectronic device.

[0011] Technical solutions

[0012] According to an embodiment, a compound for an organic photoelectric device represented by Chemical Formula 1 is provided.

[0013] [Chemical formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] Ar 1 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[0017] L 1 is an unsubstituted biphenylene group, and

[0018] R 1 To R 8 and 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 heterocyclyl, or a combination thereof.

[0019] According to another embodiment, a composition for an organic optoelectronic device includes: a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device, wherein the first compound for the organic optoelectronic device is represented by Chemical Formula 1, and the second compound for the organic optoelectronic device is represented by Chemical Formula 2, or a combination of Chemical Formula 3 and Chemical Formula 4.

[0020] [Chemical formula 2]

[0021]

[0022] In chemical formula 2,

[0023] Y 1 and Y 2 are independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group,

[0024] L 2 and L 3 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0025] R a and R 9 To R 12 are independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, and

[0026] m is an integer from 0 to 2;

[0027]

[0028] In Chemical Formula 3 and Chemical Formula 4,

[0029] Y 3 and Y 4 are independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group,

[0030] Two adjacent * in chemical formula 3 are connected to chemical formula 4,

[0031] The * in Chemical Formula 3 not connected to Chemical Formula 4 is independently CL a -R b ,

[0032] L a , L 4 and L 5 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

[0033] R b and R 13 To R 16 and R is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.

[0034] According to another embodiment, an organic optoelectronic 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 optoelectronic device or the composition for an organic optoelectronic device.

[0035] According to another embodiment, a display device including an organic photoelectric device is provided.

[0036] Effects of the Invention

[0037] An organic photoelectric device with high efficiency and long life can be achieved. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 and Figure 2 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0039]

Explanation of symbols

[0040] 100, 200: Organic light-emitting diodes

[0041] 105: organic layer

[0042] 110: cathode

[0043] 120: Anode

[0044] 130: Luminous layer

[0045] 140: Hole auxiliary layer DETAILED DESCRIPTION

[0046] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary and the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0047] In the present specification, when a definition is not otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium (D), halogen, hydroxyl, amine, 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.

[0048] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a 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, or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a 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 of a substituent or a compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, cyano, or C1 to C5 alkylsilyl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, trimethylsilyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0049] In the present specification, when a definition is not otherwise provided, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S, P and Si in one functional group and the rest are carbon.

[0050] In the present specification, "aryl group" refers to 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 (e.g., phenyl, naphthyl, etc.), a group in which two or more hydrocarbon aromatic parts can be connected by a σ bond (e.g., biphenyl, terphenyl, quaterphenyl, etc.), and a group in which two or more hydrocarbon aromatic parts are directly or indirectly fused to provide a non-aromatic fused ring (e.g., fluorenyl), etc.

[0051] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0052] In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may contain at least one heteroatom selected from N, O, S, P and Si to replace carbon (C) in a cyclic compound (e.g., aryl group, cycloalkyl group, condensed ring thereof, or a combination 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.

[0053] For example, "heteroaryl" refers to an aryl group containing 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 contains 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.

[0054] More specifically, the substituted or unsubstituted C6 to 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 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 m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The present invention can include, but is not limited to, chrysenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, or a combination thereof.

[0055] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furanyl, a substituted or unsubstituted thiophenyl, 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 substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, The invention also includes substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but is not limited thereto.

[0056] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conduction characteristics according to the highest occupied molecular orbital (HOMO) energy level.

[0057] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and the electrons formed in the cathode can be easily injected into the light emitting layer and transported in the light emitting layer due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0058] Hereinafter, compounds according to Examples are described.

[0059] The compound according to the embodiment is represented by Chemical Formula 1.

[0060] [Chemical formula 1]

[0061]

[0062] In Chemical Formula 1,

[0063] Ar 1 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[0064] L 1 is an unsubstituted biphenylene group, and

[0065] R 1 To R 8 and 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 heterocyclyl, or a combination thereof.

[0066] The compound represented by Chemical Formula 1 may have a structure in which one carbazole group is directly connected to triazine without a connecting group in the N-direction, and another carbazole group is connected to triazine in the N-direction through a biphenylene group with triazine as a core.

[0067] Since one carbazole group is directly linked to the triazine without a linking group in the N-direction (ie, at the 9-position), the compound may have a relatively low LUMO energy level and thus have advantages in electron injection and transport.

[0068] Furthermore, since another carbazole group is linked to triazine in the N-direction (i.e., at the 9-position), the π bond through the CN bond is broken, and thus the electron cloud between HOMO-LUMO can be clearly localized in the hole transport portion and the electron transport portion, and such localization can occur more efficiently because the carbazole group is linked to triazine through the biphenylene group, and as a result, the lifespan improvement effect can be maximized.

[0069] In other words, in a device including the compound represented by Chemical Formula 1, hole / electron injection and transport may be facilitated, and an electron cloud may be effectively localized, and thus a stable structure of both electrons and holes is achieved, and thus more favorable characteristics of lifetime may be obtained.

[0070] Specifically, the compound includes triazine as a central core and thus can ensure rapid electron injection and mobility, and has charge balance with a carbazole portion having strong hole mobility, which can greatly contribute to long life characteristics.

[0071] For example, L 1 It can be one of the connection groups selected from group I.

[0072] [Group I]

[0073]

[0074] In Group I, *a1 is a linking portion to the triazine of Chemical Formula 1, and *a2 is a linking portion to the carbazole of Chemical Formula 1.

[0075] Specifically, the biphenylene group can be a combination of para- and meta-linked groups, for example, L 1 Can be expressed as L-2 or L-4.

[0076] For example, Ar 1 It may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0077] For example, Ar 1 may be phenyl substituted or unsubstituted by deuterium (D), phenyl substituted or unsubstituted by cyano, phenyl substituted or unsubstituted by C1 to C5 alkylsilyl, biphenyl substituted or unsubstituted by deuterium (D), biphenyl substituted or unsubstituted by cyano, or biphenyl substituted or unsubstituted by C1 to C5 alkylsilyl, and

[0078] According to one embodiment, Ar 1 The group may be a deuterium-substituted or unsubstituted phenyl group, a cyano-substituted or unsubstituted phenyl group, a C1-C5 alkylsilyl-substituted or unsubstituted phenyl group, or an unsubstituted biphenyl group.

[0079] In the most specific embodiment, Ar 1 It may be an unsubstituted phenyl group, but is not limited thereto.

[0080] For example, R1 to R4 may independently be hydrogen, deuterium, cyano, halogen, C1 to C10 alkyl or C6 to C12 aryl, and

[0081] For example, R 1 To R 4 may independently be hydrogen, cyano, C1 to C5 alkyl or phenyl, and

[0082] In the most specific embodiment, R 1 To R 4 It may be entirely hydrogen, but is not limited thereto.

[0083] For example, R 5 To R 8 may independently be hydrogen, deuterium, cyano, halogen, C1 to C10 alkyl or C6 to C12 aryl, and

[0084] For example, R 5 To R 8 may independently be hydrogen, cyano, C1 to C5 alkyl or phenyl,

[0085] In the most specific embodiment, R 5 To R 8 It may be entirely hydrogen, but is not limited thereto.

[0086] For a specific example, Ar 1 may be an unsubstituted phenyl group, and R 5 To R 8 It may be all hydrogen.

[0087] For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one of the compounds of Group 1, but is not limited thereto.

[0088] [Group 1]

[0089]

[0090] According to another embodiment, a composition for an organic optoelectronic device includes: a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device, wherein the first compound for the organic optoelectronic device is represented by Chemical Formula 1, and the second compound for the organic optoelectronic device is represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4.

[0091] [Chemical formula 2]

[0092]

[0093] In chemical formula 2,

[0094] Y 1 and Y 2 are independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group,

[0095] L 2 and L 3 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0096] R a and R 9 To R 12 are 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 heterocyclyl, and

[0097] m is an integer from 0 to 2;

[0098]

[0099] In Chemical Formula 3 and Chemical Formula 4,

[0100] Y 3 and Y 4 are independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group,

[0101] Two adjacent * in chemical formula 3 are connected to chemical formula 4,

[0102] The * in Chemical Formula 3 not connected to Chemical Formula 4 is independently CL a -R b ,

[0103] L a , L 4 and L 5 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

[0104] R b and R 13 To R 16 and R is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.

[0105] The second compound for an organic photoelectric device may be used in a light-emitting layer together with the first compound for an organic photoelectric device to improve light-emitting efficiency and lifespan characteristics by increasing charge mobility and stability.

[0106] For example, Y in Chemical Formula 2 1 and Y 2 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted pyridyl,

[0107] L in chemical formula 2 2 and L 3 may independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0108] R in chemical formula 2 9 To R 12 may independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0109] m can be 0 or 1.

[0110] For example, “substituted” in Chemical Formula 2 means that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0111] In a specific embodiment of the present invention, Chemical Formula 2 can be represented by one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0112]

[0113]

[0114] In Chemical Formulae 2-1 to 2-15, R 9 To R 12 may be independently hydrogen, or a substituted or unsubstituted C6 to C12 aryl group, and *-L 2 -Y 1 and*-L 3 -Y 2 may independently be one of the substituents in Group II.

[0115] [Group Ⅱ]

[0116]

[0117] In Group II, * is a linking moiety.

[0118] In an embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0119] In addition, *-L in Chemical Formula 2-8 1 -Y 1 and*-L 2 -Y 2 It may be independently Group II, and may be, for example, one of B-1, B-2, and B-3.

[0120] In the most specific embodiment, *-L 1 -Y 1 and*-L 2 -Y 2 All of them can be represented by B-2 of Group II, but are not limited thereto.

[0121] For example, the second compound for an organic optoelectronic device represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0122]

[0123] In Chemical Formulae 3A to 3E, Y 3 and Y 4 , L 4 and L 5 and R 13 To R 16 Same as above,

[0124] L a1 To L a4 With the above L 4 and L 5 The same, and

[0125] R b1 To R b4 With the above R 13 To R 16 same.

[0126] For example, Y in Chemical Formula 3 and Chemical Formula 4 3 and Y 4 may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0127] R b1 To R b4 and R13 To R 16 and R is independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0128] In one specific embodiment of the present invention, Y in Chemical Formula 3 and Chemical Formula 4 3 and Y 4 The substituents may be independently selected from Group III.

[0129] [Group III]

[0130]

[0131] In group III, * represents the connecting moieties to L4 and L5, respectively.

[0132] In an embodiment, R b1 To R b4 and R 13 To R 16 and R is independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0133] For example, R b1 To R b4 and R 13 To R 16 may independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0134] In a specific embodiment, R b1 To R b4 may independently be hydrogen, and R 13 To R 16 may independently be hydrogen or phenyl.

[0135] In a specific embodiment of the present invention, the second compound for an organic optoelectronic device may be represented by Chemical Formula 2-8 or Chemical Formula 3C.

[0136] In this article, Y in Chemical Formulae 2-8 and Chemical Formula 3C 1 To Y 4 L may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, 2 To L5 , L a1 and L a2 may independently be a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R b1 , R b2 and R 9 To R 16 and R is independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0137] In the most specific embodiment, *-L of Chemical Formula 2-8 and Chemical Formula 3C 2 -Y 1 、*-L 3 -Y 2 、*-L 4 -Y 3 and*-L 5 -Y 4 All of them can be represented by B-2 of Group III, but are not limited thereto.

[0138] For example, the second compound for the organic optoelectronic device may be one of the compounds selected from Group 2, but is not limited thereto.

[0139] [Group 2]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device may be included, for example, in a weight ratio of 1:99 to 99:1. Within the range, the electron transport capability of the first compound for an organic optoelectronic device and the hole transport capability of the second compound for an organic optoelectronic device may be used to adjust the ideal weight ratio to achieve bipolar characteristics and thus improve efficiency and lifespan. Within the range, it may be, for example, a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, a weight ratio of about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50. For example, the weight ratio may be a weight ratio of 20:80 to 40:60, and for a specific example, the weight ratio may be a weight ratio of 30:70, 40:60, or 50:50. More specifically, it may be a weight ratio of 30:70 or 50:50.

[0151] At least one compound may be included in addition to the first compound for an organic photoelectric device and the second compound for an organic photoelectric device.

[0152] The compound for an organic photoelectric device or the composition for an organic photoelectric device may be a composition further including a dopant.

[0153] The dopant may be, for example, a phosphorescent dopant, may be, for example, a red, green, or blue phosphorescent dopant, may be, for example, a red or green phosphorescent dopant.

[0154] The dopant is mixed in a small amount in a compound or composition for an organic optoelectronic device to induce light emission, and generally can be a material that emits light by multiple excitations to a triplet state or more than a triplet state, such as a metal complex. The dopant can be, for example, an inorganic compound, an organic compound, or an organic / inorganic compound, and one or more kinds thereof can be used.

[0155] The dopant may be, for example, a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including 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 chemical formula Z, but is not limited thereto.

[0156] [Chemical formula Z]

[0157] L 5 MX a

[0158] In the chemical formula Z, M is a metal, and L 5 With X a are the same or different and are ligands that form a complex compound with M.

[0159] 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 and X may be, for example, bidendate ligands.

[0160] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be formed by dry film deposition such as chemical vapor deposition (CVD).

[0161] Hereinafter, an organic optoelectronic device including the compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0162] The organic optoelectronic device may be any element that converts electrical energy into optical energy and vice versa, but is not particularly limited, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0163] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the drawings.

[0164] Figure 1 and Figure 2 is a cross-sectional view of an organic light emitting diode according to an embodiment.

[0165] Reference Figure 1 , the organic light emitting diode 100 according to the 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 .

[0166] The anode 120 may be made of a conductor having a large 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 be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0167] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; a multi-layer structure material, such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0168] The organic layer 105 may include a compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0169] The organic layer 105 may include a light-emitting layer 130 , and the light-emitting layer 130 may include a compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0170] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light-emitting composition.

[0171] The light emitting layer 130 may include the above-described first compound for an organic photoelectric device and the second compound for an organic photoelectric device as examples of phosphorescent hosts.

[0172] The organic layer may further include an auxiliary layer in addition to the light emitting layer.

[0173] The auxiliary layer may be, for example, a hole auxiliary layer 140 .

[0174] Reference Figure 2 , the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130. The hole auxiliary layer 140 can further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0175] The hole assisting layer 140 may include, for example, at least one of the compounds of Group A.

[0176] In more detail, 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, and at least one of the compounds of group D may be included in the hole transport auxiliary layer.

[0177] [Group D]

[0178]

[0179]

[0180]

[0181] In addition to the above compounds, the hole transport auxiliary layer may also include known compounds such as US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and compounds having similar structures.

[0182] In an embodiment, Figure 1 or Figure 2 In the embodiment, the organic light emitting diode may further include an electron transport layer, an electron injection layer or a hole injection layer as the organic layer 105 .

[0183] 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 using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating; and forming a cathode or an anode on the organic layer.

[0184] Organic light emitting diodes can be applied to organic light emitting display devices.

[0185] Hereinafter, the embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of the present invention is not limited thereto.

[0186] Embodiments of the invention

[0187] Unless otherwise noted, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or were synthesized by known methods.

[0188] (Preparation of compounds for organic optoelectronic devices)

[0189] A compound as a specific example of the present invention was synthesized by the following steps.

[0190] (Preparation of a first compound for an organic photoelectric device)

[0191] Synthesis Example 1: Synthesis of Intermediate A

[0192]

[0193] 58.81 g (260.15 mmol) of 2-phenyl-4,6-dichlorotriazine and 30 g (2-phenyl-4,6-dichlorotriazine) (179.42 mmol) of carbazole were suspended in 500 ml of tetrahydrofuran (THF), and 18.11 g of NaO(t-Bu) was slowly added thereto, and then stirred 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 A as the target compound.

[0194] (LC / MS: theoretical value: 356.81, measured value: 357.30)

[0195] Synthesis Example 2: Synthesis of Intermediate B

[0196]

[0197] 30.29 g (105 mmol) of 3-(9H-carbazole-9-yl)phenyl boronic 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, an organic layer was extracted therefrom, and then the organic layer was concentrated and subjected to silica gel column chromatography to obtain 35 g (yield: 94%) of Intermediate B as a target compound.

[0198] Synthesis Example 3: Synthesis of Intermediate C

[0199]

[0200] 35 g (100 mmol) of Intermediate B synthesized according to Synthesis Example 2, 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 dimethylformamide (DMF), and then refluxed and stirred for 12 hours. When the reaction was completed, distilled water was added to the reaction solution, and then extraction / concentration with dichloromethane and silica gel column chromatography were performed to obtain 30.8 g (yield: 70%) of Intermediate C as the target compound.

[0201] Synthesis Example 4: Synthesis of Compound A-1

[0202]

[0203] 5 g (14.01 mmol) of intermediate A, 6.86 g (15.41 mmol) of intermediate C, 0.49 g (0.42 mmol) of Pd(PPh3)4 and 3.87 g (28.03 mmol) of K2CO3 were suspended in 100 ml of THF and 50 ml of distilled water, and then refluxed and stirred for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, and the solid produced therein was filtered and washed with distilled water and acetone. Subsequently, the solid was heated with 200 ml of toluene and dissolved therein, and then filtered with silica gel, the filtrate was cooled to room temperature, and the solid produced therein was filtered, washed with acetone, and dried to obtain 6.7 g of compound A-1 (yield: 74%).

[0204] (LC / MS: theoretical value: 639.75, measured value: 640.45)

[0205] Synthesis Example 5: Synthesis of Intermediate D

[0206]

[0207] 20 g (69.66 mmol) of 4-(9H-carbazole-9-yl)phenyl boronic acid, 13.34 g (69.66 mmol) of 1-bromo-3-chlorobenzene, 2.42 g (2.09 mmol) of Pd(PPh3)4 and 19.25 g (139.31 mmol) of K2CO3 were suspended in 300 ml of THF and 150 ml of distilled water, and then synthesis was carried out according to the same method as in Synthesis Example 2 to obtain 19.82 g (yield: 81%) of intermediate D.

[0208] Synthesis Example 6: Synthesis of Intermediate E

[0209]

[0210] 17 g (yield: 68%) of Intermediate E was synthesized according to the same method as Synthesis Example 3, except that 19.82 g (56.01 mmol) of Intermediate D synthesized according to Synthesis Example 5 was used.

[0211] Synthesis Example 7: Synthesis of A-3

[0212]

[0213] 6 g (yield: 74%) of compound A-3 was synthesized according to the same method as Synthesis Example 4, except that 4.55 g (12.7 mmol) of Intermediate A synthesized according to Synthesis Example 1 and 5.79 g (13.01 mmol) of Intermediate E synthesized according to Synthesis Example 6 were used.

[0214] (LC / MS: theoretical value: 639.75, measured value: 640.44)

[0215] Synthesis Example 8: Synthesis of Comparative Compound R1

[0216]

[0217] 5.0 g (11.23 mmol) of intermediate C synthesized according to Synthesis Example 3, 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, 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 recrystallized in monochlorobenzene to obtain 4 g (yield: 65%) of comparative compound R1.

[0218] (LC / MS: theoretical value: 550.65, measured value: 551.4)

[0219] Synthesis Example 9: Synthesis of Intermediate F

[0220]

[0221] 10 g (54.23 mmol) of cyanuric chloride and 18.13 g (108.45 mmol) of carbazole were suspended in 250 ml of THF, and 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, and then washed with distilled water and acetone / hexane to obtain 12 g (yield: 49.6%) of Intermediate F.

[0222] Synthesis Example 10: Synthesis of Comparative Compound R2

[0223]

[0224] 6 g (13.46 mmol) of intermediate F synthesized according to Synthesis Example 9, 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, and then stirred for 12 hours. When the reaction was completed, the solid produced therein was filtered and washed with distilled water / acetone. The solid was heated with 300 ml of dichlorobenzene and dissolved therein, and then filtered with silica gel, the filtrate was cooled to room temperature, and the solid produced therein was filtered and dried to obtain 3.9 g (yield: 40%) of comparative compound R2.

[0225] (LC / MS: theoretical value: 728.84, measured value: 729.6)

[0226] Synthesis Example 11: Synthesis of Intermediate G

[0227]

[0228] 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) was slowly added thereto at 0° C. When the reaction was completed, the solid produced therein was filtered and then washed with distilled water / acetone / hexane to obtain 10 g (yield: 16%) of intermediate G as a target compound.

[0229] Synthesis Example 12: Synthesis of Intermediate H

[0230]

[0231] 4.9 g (15.55 mmol) of Intermediate G synthesized according to Synthesis Example 11, 6.69 g (15.55 mmol) of Intermediate I (refer to Synthesis Example 3 of Korean Patent Publication No. 10-2014-0135524), 0.89 g (0.78 mmol) of Pd(PPh3)4 and 5.37 g (38.87 mmol) of K2CO3 were suspended in 50 ml of THF / 50 ml of toluene / 50 ml of distilled water, and then stirred for 12 hours. When the reaction was completed, the solid produced therein was filtered, washed with distilled water / acetone and dried to obtain 5 g (yield: 56%) of Intermediate H as the target compound.

[0232] Synthesis Example 13: Synthesis of Comparative Compound R3

[0233]

[0234] 2.4 g (4.11 mmol) of Intermediate H synthesized according to Synthesis Example 12, 1.67 g (4.53 mmol) of 9-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole, 0.14 g (0.12 mmol) of Pd(PPh3)4 and 1.14 g (8.23 mmol) of K2CO3 were suspended in 50 ml of THF and 50 ml of deionized water (DIW), and then refluxed and stirred for 12 hours. When the reaction was completed, the solid produced therein was filtered and then washed with distilled water and acetone. The solid was heated with 100 ml of dichlorobenzene and dissolved therein, and then filtered with silica gel, and the filtrate 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 as the target compound.

[0235] (LC / MS: theoretical value: 789.92, measured value: 790.40)

[0236] (Preparation of a Second Compound for an Organic Photoelectric Device)

[0237] Synthesis Example 14: Synthesis of Compound B-99

[0238] Compound B-99 was synthesized in the same manner as known in US2017-0317293A1.

[0239] Synthesis Example 15: Synthesis of Compound C-4

[0240]

[0241] 8 g (31.2 mmol) of 5,8-dihydroindolo[2,3-c]carbazole (CAS: 200339-30-6), 20.5 g (73.32 mmol) of 4-iodobiphenly, 1.19 g (6.24 mmol) of CuI, 1.12 g (6.24 mmol) of 1,10-phenanthoroline and 12.9 g (93.6 mmol) of K2CO3 were put into a round bottom flask, and 50 ml of DMF was added thereto, and then refluxed and stirred for 24 hours under nitrogen. When the reaction was completed, distilled water was added thereto to extract crystals, and the crystals were filtered. The solid was dissolved in 250 mL of xylene, and then subjected to silica gel filtration and extraction as a white solid to obtain 16.2 g (yield: 93%) of compound C-4.

[0242] LC / MS calculated results: C42H28N2 exact mass: 560.2252, found: 561.23

[0243] (Manufacturing of organic light-emitting diodes)

[0244] Example 1

[0245] A glass substrate coated with indium tin oxide (ITO) having a film thickness of 1500 angstroms was washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, methanol, etc. and dried, then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. Using the obtained indium tin oxide transparent electrode as an anode, compound A was vacuum deposited on the indium tin oxide substrate to form a 700 angstrom thick hole injection layer, and compound B was deposited on the injection layer to a thickness of 50 angstroms, and then compound C was deposited to a thickness of 1020 angstroms to form a hole transport layer. On the hole transport layer, a 400 angstrom thick light-emitting layer was formed by vacuum deposition using A-1 of Synthesis Example 4 as a main body and 7 wt% of PhGD as a dopant. Subsequently, a 300 angstrom thick electron transport layer was formed on the light emitting layer by simultaneously vacuum depositing compound D and Liq at a ratio of 1:1, and on the electron transport layer, Liq and Al were sequentially vacuum deposited to 15 angstrom and 1200 angstrom thick, thereby manufacturing an organic light emitting diode.

[0246] The organic light emitting diode has a five-layer organic thin layer, and specifically has the following structure.

[0247] ITO / Compound A (700 angstroms) / Compound B (50 angstroms) / Compound C (1020 angstroms) / EML [A-1: PhGD (7 wt %)] (400 angstroms) / Compound D: Liq (300 angstroms) / Liq (15 angstroms) / Al (1200 angstroms).

[0248] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine

[0249] Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN)

[0250] Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0251] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0252]

[0253] Examples 2 to 9 and Comparative Examples 1 to 5

[0254] Each diode of Examples 2 to 9 and Comparative Examples 1 to 5 was manufactured according to the same method as Example 1, except that the bodies and ratios thereof were changed as shown in Tables 1 to 5.

[0255] Assessment: Lifespan increase synergy

[0256] Lifespan characteristics of the organic light emitting diodes according to Examples 1 to 9 and Comparative Examples 1 to 5 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 1 to 5.

[0257] (1) Measurement life

[0258] The T90 lifetime of the organic light emitting diodes according to Examples 1 to 9 and Comparative Examples 1 to 5 was measured at an initial brightness of 24,000 cd / m 2 ) emits light and its brightness decreases over time using the Polanonix lifetime measurement system. When its brightness is relative to the initial brightness (cd / m 2 ) is reduced to 90%.

[0259] (2) Calculate T90 life ratio (%)

[0260] Relative comparison of T90(h) between single host or mixed host examples with the same second host (first compound as first host) and mixed host comparative examples (comparative compound as first host).

[0261] T90 life ratio (%) = {[[T90(h) of Example (first compound used alone or as a main component of a mixture)] / [[T90(h) of Comparative Example (comparative compound used alone or as a main component of a mixture)]}×100

[0262] [Table 1]

[0263] category Single Entity T90 life ratio (%) Example 1 A-1 180％ Example 2 A-3 150％ Comparative Example 1 R1 100％

[0264] [Table 2]

[0265] category Single Entity T90 life ratio (%) Example 3 A-1 350％ Example 4 A-3 300％ Comparative Example 2 R2 100％

[0266] [Table 3]

[0267] category Single Entity T90 life ratio (%) Example 5 A-1 192％ Example 6 A-3 143％ Comparative Example 3 R3 100％

[0268] [Table 4]

[0269]

[0270] [Table 5]

[0271]

[0272] Referring to Tables 1 to 5, the compounds according to the present invention showed significantly improved lifespans compared to the comparative compounds.

[0273] Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and it should be clearly understood that many changes and modifications made by those skilled in the art using the basic concepts of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. A compound for an organic optoelectronic device, represented by Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, Ar 1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, R 1 To R 8 are independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, and "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl, cyano, or C1 to C5 silyl, and L 1 A linking group selected from Group I: [Group I] In Group I, *a1 is a connecting portion to the triazine of Chemical Formula 1, and *a2 is a connecting portion to the carbazole of Chemical Formula 1.

2. The compound for an organic optoelectronic device according to claim 1, wherein L 1 Indicated by L-2 or L-4.

3. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 is unsubstituted or deuterium-substituted phenyl, unsubstituted or cyano-substituted phenyl, unsubstituted or C1-C5 silyl-substituted phenyl, or unsubstituted biphenyl.

4. The compound for an organic optoelectronic device according to claim 1, which is a compound of Group 1: [Group 1] 5. A composition for an organic optoelectronic device, comprising A first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device, The first compound used in the organic photoelectric device is represented by the chemical formula 1 according to claim 1, The second compound for the organic photoelectric device is represented by Chemical Formula 2-8 or Chemical Formula 3C: [Chemical formula 2-8] in, In Chemical Formula 2-8, Y 1 and Y 2 are independently C6 to C20 aryl or C2 to C30 heterocyclic, L 2 and L 3 are independently a single bond or a C6 to C20 arylene group, and R 9 To R 12 are independently hydrogen, deuterium, cyano, halogen, amine, C1 to C30 alkyl, C6 to C30 aryl, or C2 to C30 heterocyclic, and m is an integer from 0 to 2; [Chemical formula 3C] Wherein in chemical formula 3C, Y 3 and Y 4 are independently C6 to C20 aryl or C2 to C30 heterocyclic, L a1 , L a2 , L 4 and L 5 are independently a single bond, or a C6 to C20 arylene group, and R b1 , R b2 and R 13 To R 16 are independently hydrogen, deuterium, cyano, halogen, amine, C1 to C30 alkyl, C6 to C30 aryl, or C2 to C30 heterocyclic.

6. The composition for an organic optoelectronic device according to claim 5, where Y 1 To Y 4 are independently phenyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, L 2 To L 5 , L a1 and L a2 are independently a single bond, or a C6 to C20 arylene group, and R b1 , R b2 and R 9 To R 16 are independently hydrogen, deuterium, cyano, phenyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.

7. The composition for an organic optoelectronic device according to claim 6, Where R 9 To R 12 are independently hydrogen, deuterium or C6 to C12 aryl, and *-L 2 -Y 1 and*-L 3 -Y 2 is independently one of the substituents of Group II, [Group Ⅱ] in, In Group II, * is a linking moiety.

8. The composition for an organic optoelectronic device according to claim 7, wherein *-L 2 -Y 1 and*-L 3 -Y 2 Independently, B-1, B-2 and B-3 of Group II.

9. The composition for an organic optoelectronic device according to claim 6, wherein Y 3 and Y 4 are independently phenyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.

10. The composition for an organic optoelectronic device according to claim 9, wherein Y 3 and Y 4 is independently one of the substituents of Group III: [Group III] in, In Group III, * respectively with L 4 and L 5 The connecting part.

11. An organic optoelectronic device comprising The anode and cathode face each other, at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound for the organic optoelectronic device according to any one of claims 1 to 4; or The composition for the organic optoelectronic device according to any one of claims 5 to 10.

12. The organic optoelectronic device according to claim 11, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for the organic photoelectric device or the composition for the organic photoelectric device. 13 . A display device comprising the organic optoelectronic device according to claim 11 .

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