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

Abstract

To provide a compound for an organic optoelectronic device capable of implementing an organic optoelectronic device having high efficiency and a long life-span, a composition for an organic optoelectronic device that includes the compound, an organic optoelectronic device that includes the compound, and a display apparatus that includes the organic optoelectronic device.SOLUTION: Disclosed are a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device including the same, an organic optoelectronic device and a display apparatus. Details of Chemical Formula 1 are as described in the specification.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. [Background technology]

[0002] An organic optoelectronic diode is a device that can convert electrical energy and optical energy into each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principle: one is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, which are then transferred to different electrodes to generate electrical energy, and the other is a light-emitting device in which voltage or current is supplied to the electrodes to generate light energy from electrical energy.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

[0005] Among these, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by the organic material located between the electrodes. Summary of the Invention [Problem to be solved by the invention]

[0006] One embodiment of the present invention provides a compound for an organic optoelectronic device that can realize an organic optoelectronic device with high efficiency and long life. Another embodiment provides a composition for an organic optoelectronic device comprising the compound. Yet another embodiment provides an organic optoelectronic device comprising the compound. Yet another embodiment provides a display device including the organic optoelectronic device. [Means for solving the problem]

[0007] According to one embodiment of the present invention, there is provided a compound for an organic optoelectronic device represented by the following Chemical Formula 1:

[0008] [ka]

[0009] In the above Chemical Formula 1, L 1 ~L 3 each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, R 1 ~R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0010] According to another embodiment of the present invention, there is provided a composition for an organic optoelectronic device comprising a first compound and a second compound.

[0011] The first compound is the compound for an organic optoelectronic device described above, and the second compound is represented by the following chemical formula 2.

[0012] [ka]

[0013] In the above Chemical Formula 2, X 1 O, S, NR a , C.R. b R c or SiR d R e and R a , R b , R c , R d , R e and R 11 ~R 14 each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; A is any one selected from the rings listed in Group II and Group III below, [ka] In Group II and Group III, * is the connection point, X 2 O, S, NR f , C.R. g R h or SiR i R j and R f , R g , R h , R i , R j and R 15 ~R 21 each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; R 11 ~R 14 and R 15 ~R 21 At least one of the groups is a group represented by the following chemical formula a: [ka] In the chemical formula a, L 4 ~L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, Ar 3 and Ar 4 each independently represents a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, * is the connection point.

[0014] According to yet another embodiment, there is provided an organic optoelectronic device comprising a positive electrode and a negative electrode facing each other, and at least one organic layer located between the positive electrode and the negative electrode, wherein the organic layer comprises the compound for organic optoelectronic devices or the composition for organic optoelectronic devices. According to yet another embodiment, there is provided a display device including the organic optoelectronic device. [Effects of the Invention]

[0015] The present invention can realize an organic optoelectronic device with high efficiency and long life. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. [Figure 2] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. [Figure 3] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. [Figure 4] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0017] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is provided by way of example only and is not intended to limit the scope of the present invention, which is defined solely by the scope of the claims that follow.

[0018] In this specification, unless otherwise defined, the term "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a nitro group, a substituted or unsubstituted silyl group having 1 to 40 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a trifluoroalkyl group having 1 to 10 carbon atoms, a cyano group, or a combination thereof.

[0019] In one embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a cyano group. In another embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a cyano group. In yet another embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a cyano group. In yet another embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is replaced with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0020] In this specification, unless otherwise defined, "hetero" means that 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.

[0021] In this specification, the term "aryl group" is a general concept for groups having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group or naphthyl group; a form in which two or more hydrocarbon aromatic moieties are linked by a sigma bond, such as a biphenyl group, a terphenyl group or a quaterphenyl group; and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group.

[0022] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0023] As used herein, the term "heterocyclic group" is a generic term that includes a heteroaryl group and refers to a group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

[0024] For example, a "heteroaryl group" refers to an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups can be directly linked by a sigma bond, or, if the heteroaryl group contains two or more rings, the two or more rings can be fused to each other. If the heteroaryl group is a fused ring, each ring can contain 1 to 3 of the heteroatoms.

[0025] More specifically, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be, but is not limited to, 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 chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof.

[0026] More specifically, the substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms 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 pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, The alkyl group may be, but is not limited to, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl 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 dibenzothiophenyl group, or a combination thereof.

[0027] In this specification, the term "hole characteristic" refers to the ability to donate electrons and form holes when an electric field is applied, and refers to the ability to have conductive properties due to the HOMO level, facilitating the injection of holes formed in the positive electrode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the positive electrode, and the movement of holes in the light-emitting layer.

[0028] The electronic properties refer to the ability to receive electrons when an electric field is applied, and refer to the properties of a material that has conductive properties due to the LUMO level and facilitates the injection of electrons formed in the negative electrode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the negative electrode, and the movement of electrons in the light-emitting layer.

[0029] Hereinafter, a compound for an organic optoelectronic device according to one embodiment of the present invention will be described. A compound for an organic optoelectronic device according to one embodiment of the present invention is represented by the following Chemical Formula 1:

[0030] [ka]

[0031] In the above Chemical Formula 1, L 1 ~L 3 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, R 1 ~R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0032] The compound represented by Chemical Formula 1 has a structure in which a chrysene terminal is substituted with a triazine.

[0033] Substitution of triazine at the end of chrysene increases the conjugation length compared to central conjugation, resulting in a stable molecule with a long lifespan. Furthermore, condensation of the aromatic ring can enhance ring stabilization and maximize lifespan.

[0034] The formula 1 can be represented by any one of the following formulas 1-1 to 1-4 depending on the specific substitution site of the triazine.

[0035] [ka] [ka]

[0036] In the above Chemical Formulas 1-1 to 1-4, L 1 ~L 3 , Ar 1 and Ar 2 and R 1 ~R 10 is as described above.

[0037] The compound for an organic optoelectronic device according to one embodiment of the present invention is represented by any one of Chemical Formula 1-1, Chemical Formula 1-2, and Chemical Formula 1-4.

[0038] In one embodiment of the present invention, the Ar 1 and Ar 2 At least one of these may be a substituted or unsubstituted aryl group having 10 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0039] In one specific embodiment of the present invention, the Ar 1 and Ar 2 At least one of may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0040] In one embodiment of the present invention, the L 1 ~L 3 may each independently be a single bond or a substituted or unsubstituted phenylene group.

[0041] For example, the L 1 is a single bond, and the Ar 1 and Ar 2are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and 1 and Ar 2 At least one of may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0042] For example, the L 1 is a substituted or unsubstituted phenylene group, 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0043] As a more specific example, * -L 2 -Ar 1 and * -L 3 -Ar 2 are each independently selected from the substituents listed in Group I below.

[0044] [ka]

[0045] In Group I, * is the connection point. For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0046] [ka] [ka] [ka] [ka] [ka]

[0047] According to another embodiment, the composition for an organic optoelectronic device includes a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device described above, and the second compound is represented by the following Chemical Formula 2:

[0048] [ka]

[0049] In the above Chemical Formula 2, X 1 O, S, NR a , C.R. b R c or SiR d R e and R a , R b , R c , R d , R e and R 11 ~R 14 each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; A is any one selected from the rings listed in Group II and Group III below, [ka] In Group II and Group III, * is the connection point, X 2 O, S, NR f , C.R. g R h or SiR i R j and R f , R g , R h , R i , R j and R 15 ~R 21 each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; R 11 ~R 14 and R 15 ~R 21 At least one of the groups is a group represented by the following chemical formula a: [ka] In the chemical formula a, L 4 ~L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, Ar 3 and Ar 4 each independently represents a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, * is the connection point.

[0050] The second compound may have a structure in which carbazole / fused carbazole / fused dibenzofuran / fused dibenzothiophene / fused dibenzosilole is substituted with an amine, and is represented by, for example, any one of the following Chemical Formulas 2-I to 2-IX depending on the type and condensation position of the additional benzene ring.

[0051] [ka]

[0052] In the above Chemical Formula 2-I to Chemical Formula 2-IX, X 1 , X 2 , R 11 ~R 21 is as described above.

[0053] Depending on the substitution direction of the amine group, the second compound is represented by any one of the following chemical formulas 2-IA to 2-IXA, 2-IB to 2-IXB, and 2-IC to 2-IIIC.

[0054] [ka] [ka] [ka]

[0055] In the above Chemical Formulae 2-IA to 2-IXA, 2-IB to 2-IXB, and 2-IC to 2-IIIC, X 1 , X 2 , L 2 ~L 4 , Ar 3 and Ar 4 is as described above, R 11 ~R 21are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0056] The second compound according to one embodiment is represented by any one of Formula 2-VIIIA, Formula 2-IVB, and Formula 2-VIIIB.

[0057] As an example, X in Formula 2-VIIIA 1 is O or S, and X 2 is CR g R h or SiR i R j may be.

[0058] As an example, X in the above-mentioned chemical formula 2-VIIIB 1 is O or S, and X 2 is CR g R h or SiR i R j may be.

[0059] As an example, X in Formula 2-VIIIA 1 is CR g R h or SiR i R j and X 2 may be O or S.

[0060] As an example, X in the above-mentioned chemical formula 2-VIIIB 1 is CR g R h or SiR i R j and X 2 may be O or S.

[0061] where R g , R h , R i and R jmay each independently be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0062] The second compound according to a specific embodiment is represented by any one of the following formulas 2-VIIIA-2, 2-IVB-2, and 2-VIIIB-2.

[0063] [ka]

[0064] In the above Chemical Formula 2-VIIIA-2, Chemical Formula 2-IVB-2 and Chemical Formula 2-VIIIB-2, L 4 ~L 6 each independently represents a single bond or a substituted or unsubstituted phenylene group; The Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group; X 1 is NR a ,O,S,CR b R c or SiR d R e and X 2 is O, S, CR g R h or SiR i R j and R a , R b , R c , R d , R e , R g , R h , R i and R j are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, R 11~R 15 and R 19 ~R 21 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0065] As an example, the above L 5 and L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0066] As an example, the Ar 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, or a substituted or unsubstituted benzothiophenefluorenyl group.

[0067] For example, the second compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0068] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0069] The first compound and the second compound are included in a weight ratio of, for example, 1:99 to 99:1. By using the weight ratio within this range, bipolar characteristics can be achieved by utilizing the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and lifetime. Within this range, the weight ratios are, for example, about 10:90 to 90:10, about 20:80 to 80:20, and, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. Specific examples include a weight ratio of 40:60, 50:50, or 60:40.

[0070] In addition to the first and second compounds described above, one or more compounds may be further included.

[0071] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may be a composition further containing a dopant.

[0072] The dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0073] A dopant is a substance that emits light when mixed in a small amount into a compound or composition for an organic optoelectronic device, and is generally a metal complex or other substance that emits light by multiple excitation, which is excited to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more dopants may be included.

[0074] An example of the dopant is a phosphorescent dopant, and examples of the phosphorescent dopant include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant can be, for example, a compound represented by the following chemical formula Z, but is not limited to this.

[0075] [Chemical formula Z] L 5 MX In the chemical formula Z, M is a metal, and L 5 and X 3 are the same or different and are ligands that form a complex with M. The 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 the L 5 and X 3 may be, for example, a bidentate ligand.

[0076] The above-mentioned compounds or compositions for organic optoelectronic devices are formed by a dry film formation method such as chemical vapor deposition.

[0077] An organic optoelectronic device to which the above-mentioned compound for an organic optoelectronic device or composition for an organic optoelectronic device is applied will now be described.

[0078] The organic optoelectronic element is not particularly limited as long as it is an element capable of mutually converting electrical energy and optical energy, and examples thereof include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photosensitive drums.

[0079] Here, an organic light-emitting element, which is an example of an organic optoelectronic element, will be described with reference to the drawings. 1 to 4 are cross-sectional views showing an organic light-emitting device according to one embodiment of the present invention. Referring to FIG. 1, an organic light emitting device 100 according to one embodiment includes a positive electrode 120 and a negative electrode 110 facing each other, and an organic layer 105 located between the positive electrode 120 and the negative electrode 110 .

[0080] The positive electrode 120 is made of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the positive electrode 120 include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys 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 and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0081] The negative electrode 110 is made of, for example, a conductor with a low work function to facilitate electron injection, such as a metal, a metal oxide, and / or a conductive polymer. Examples of the negative electrode 110 include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium, or alloys thereof; and multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, LiF / Al, and BaF / Ca.

[0082] The organic layer 105 can include the organic optoelectronic compound or composition described above.

[0083] The organic layer 105 includes a light-emitting layer 130, which may include the above-described compound or composition for an organic optoelectronic device.

[0084] The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.

[0085] The light-emitting layer 130 may include, for example, the above-described first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device, respectively, as phosphorescent hosts.

[0086] In addition to the light-emitting layer, the organic layer may further include a charge transport region. The charge transport region may be, for example, a hole transport region 140 .

[0087] 2, the organic light-emitting device 200 further includes a hole transport region 140 in addition to the light-emitting layer 130. The hole transport region 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons. Specifically, the hole transport region 140 can 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 listed in Group E below is included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0088] [ka] [ka] [ka] [ka] [ka]

[0089] In addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds with similar structures can also be used in the hole transport region. The charge transport region may also be, for example, an electron transport region 150 .

[0090] 3, the organic light emitting device 300 includes an electron transport region 150 in addition to the light emitting layer 130. The electron transport region 150 can further enhance electron injection and / or electron mobility between the anode 110 and the light emitting layer 130 and block holes.

[0091] Specifically, the electron transport region 150 may include an electron transport layer between the negative electrode 110 and the light-emitting layer 130, and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the compounds listed in Group F below is contained in at least one of the electron transport layer and the electron transport auxiliary layer.

[0092] [ka] [ka] [ka]

[0093] One embodiment of the present invention may be an organic light emitting device including a light emitting layer 130 as the organic layer 105, as shown in FIG.

[0094] Another embodiment of the present invention may be an organic light-emitting device including a hole transport region 140 as the organic layer 105 in addition to the light-emitting layer 130, as shown in FIG.

[0095] Still another embodiment of the present invention may be an organic light-emitting device including an electron transport region 150 as the organic layer 105 in addition to the light-emitting layer 130, as shown in FIG.

[0096] Still another embodiment of the present invention may be an organic light-emitting device including, as the organic layer 105, a hole transport region 140 and an electron transport region 150 in addition to the light-emitting layer 130, as shown in FIG.

[0097] In still another embodiment of the present invention, in each of Figures 1 to 4, the organic layer 105 may be an organic light-emitting element that further includes an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer 130.

[0098] The organic light emitting devices 100, 200, 300, and 400 may be manufactured by forming an anode or cathode on a substrate, forming an organic layer by a dry film formation method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming an anode or cathode thereon.

[0099] The above-described organic light-emitting element can be applied to an organic light-emitting display device. [Example]

[0100] The above-described embodiments will be described in more detail with reference to the following examples, which are provided for illustrative purposes only and are not intended to limit the scope of the invention.

[0101] Unless otherwise specified, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or synthesized by known methods.

[0102] (Manufacturing compounds for organic photoelectron devices) The compounds presented as more specific examples of the compounds of the present invention were synthesized by the following steps.

[0103] Synthesis example 1: Synthesis of int1 [ka]

[0104] a) Synthesis of int1-1 2-Bromo-5-chlorobenzaldehyde (20.0 g, 91.1 mmol), 2-naphthaleneboronic acid (17.2 g, 100.2 mmol), Pd(PPh3)4 (5.3 g, 4.6 mmol), and K2CO3 (37.8 g, 273.4 mmol) were dissolved in 450 mL of a 2:1 volumetric mixture of tetrahydrofuran and distilled water and refluxed at 80 °C for 12 hours. After the reaction was complete, the product was purified by column chromatography (dichloromethane: n-hexane) to yield 17.6 g (72.6%) of int1-1.

[0105] b) Synthesis of int1-2 Int1-1 (17.6 g, 66 mmol) and (methoxymethyl)triphenylphosphonium chloride (24.9 g, 73 mmol) were dissolved in 130 mL of tetrahydrofuran, and potassium tert-butoxide (8.9 g, 79 mmol) was slowly added at 0°C and stirred. Upon completion of the reaction, the solvent was removed using a rotary evaporator. The mixture was extracted twice with dichloromethane and distilled water, and the organic layer was dried. Without further purification, the mixture was dissolved in 130 mL of dichloromethane, and methanesulfonic acid (12.7 g, 132 mmol) was slowly added at 0°C and stirred. Upon completion of the reaction, methyl alcohol was added to the reaction mixture to precipitate a solid, which was then filtered. The solid was then dissolved in toluene and purified through silica gel filtration to yield 8.9 g (51.4%) of int1-2.

[0106] c) Synthesis of int1 Int1-2 (8.9 g, 34 mmol), bis(pinacolato)diboron (11.2 g, 44 mmol), potassium acetate (10.0 g, 102 mmol), tricyclohexylphosphine (1.9 g, 7 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.4 g, 2 mmol) were added to 170 mL of N,N-dimethylformamide and refluxed at 150 °C for 12 h. Upon completion of the reaction, the solution was poured into excess DIW to form a precipitate. The precipitate was filtered, dissolved in boiling toluene, and filtered through silica gel. The filtered solution was directly recrystallized to yield int1 (7.1 g, 63.1%).

[0107] Synthesis example 2: Synthesis of int2 [ka]

[0108] a) Synthesis of int2 Int2 was synthesized through three steps in the same manner as int1 in Synthesis Example 1, except that 2-bromo-6-chlorobenzaldehyde was used instead of 2-bromo-5-chlorobenzaldehyde.

[0109] Synthesis example 3: Synthesis of int3 [ka]

[0110] a) int3 synthesis Int3 was synthesized through three steps in the same manner as int1 in Synthesis Example 1, except that 2-bromo-3-chlorobenzaldehyde was used instead of 2-bromo-5-chlorobenzaldehyde.

[0111] Synthesis of Synthesis Examples 4 to 10 Intermediate A and Intermediate B in Table 1 were subjected to Suzuki reaction in the same manner as in the synthesis method for int1-1 to synthesize the compounds of Synthesis Examples 4 to 10.

[0112] [Table 1]

[0113] Comparative Synthesis Example 1: Synthesis of Compound B-1 [ka]

[0114] a) Synthesis of intermediate B-1-1 Intermediate B-1-1 was synthesized using 6,12-dibromochrysene and phenylboronic acid as starting materials in the same manner as int1-1 in Synthesis Example 1, and recrystallized from toluene.

[0115] b) Synthesis of intermediate B-1-2 Intermediate B-1-1 was used as a starting material and synthesized in the same manner as int1 in Synthesis Example 1, followed by recrystallization with toluene to synthesize Intermediate B-1-2.

[0116] c) Synthesis of Compound B-1 Compound B-1 was synthesized using intermediate B-1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine as starting materials in the same manner as int1-1 in Synthesis Example 1, and recrystallized from monochlorobenzene.

[0117] Comparative Synthesis Example 2: Synthesis of Compound B-2 [ka]

[0118] a) Synthesis of intermediate B-2-1 Intermediate B-2-1 was synthesized using 3-methoxy-2-bromonaphthalene and 2-formylphenylboronic acid as starting materials in the same manner as int1-1 in Synthesis Example 1, and recrystallized from toluene.

[0119] b) Synthesis of Intermediate B-2-2 Intermediate B-2-1 was used as a starting material and synthesized in the same manner as int1-2 in Synthesis Example 1, followed by recrystallization with monochlorobenzene to synthesize intermediate B-2-2.

[0120] c) Synthesis of intermediate B-2-3 Intermediate B-2-2 was synthesized as a starting material in the same manner as the bromination of 2-methoxynaphthalene described in Tetrahedron Letters, 47(27), 4581-4584; 2006, and then recrystallized from toluene to synthesize intermediate B-2-3.

[0121] d) Synthesis of intermediate B-2-4 Intermediate B-2-3 and 1-naphthaleneboronic acid were used as starting materials and synthesized in the same manner as int1-1 of Synthesis Example 1, followed by recrystallization with monochlorobenzene to synthesize intermediate B-2-4.

[0122] e) Synthesis of intermediate B-2-5 Intermediate B-2-4 (22.0 g, 57 mmol) and pyridine hydrochloride (66 g, 572 mmol) were mixed and stirred under reflux at 200 °C for 12 hours. When the reaction was complete, the mixture was cooled to a certain temperature, distilled water was added, and the mixture was cooled completely to room temperature. Extraction was performed twice using ethyl acetate and distilled water, and silica gel filtration was performed to obtain 16.9 g (79.7%) of intermediate B-2-5.

[0123] f) Synthesis of intermediate B-2-6 Intermediate B-2-5 (16 g, 43 mmol) and triethylamine (6.6 g, 65 mmol) were dissolved in 85 mL of dichloromethane, and triflic anhydride (14.0 g, 50 mmol) was slowly added at 0°C. After the dropwise addition was complete, the mixture was heated to room temperature and stirred for 12 hours. When the reaction was complete, ice water was added, and the mixture was extracted twice with dichloromethane, and the organic layer was filtered through silica gel. Methyl alcohol was added to produce a precipitate, which was then filtered to obtain 20.1 g (92.6%) of intermediate B-2-6.

[0124] g) Synthesis of intermediate B-2-7 Intermediate B-2-6 was used as a starting material and synthesized in the same manner as int1 of Synthesis Example 1, except that the solvent was changed to dioxane, and recrystallized from toluene to synthesize intermediate B-2-7.

[0125] h) Synthesis of Compound B-2 Compound B-2 was synthesized using intermediate B-2-7 and 2-chloro-4,6-diphenyl-1,3,5-triazine as starting materials in the same manner as int1-1 in Synthesis Example 1, and recrystallized from monochlorobenzene.

[0126] Comparative Synthesis Example 3: Synthesis of Compound B-3 [ka]

[0127] a) Synthesis of intermediate B-3-1 Intermediate B-3-1 was synthesized using Intermediate B-2-2 as a starting material and purified in the same manner as in the synthesis of Intermediate B-2-5 in Comparative Synthesis Example 2.

[0128] b) Synthesis of intermediate B-3-2 Intermediate B-3-2 was synthesized by synthesizing and purifying Intermediate B-3-1 as a starting material in the same manner as in Comparative Synthesis Example 2 for Intermediate B-2-6.

[0129] c) Synthesis of Compound B-3 Compound B-3 was synthesized using intermediate B-3-2 and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine as starting materials in the same manner as int1-1 in Synthesis Example 1, and recrystallized from monochlorobenzene.

[0130] Synthesis of the second compound Synthesis Example 11: Synthesis of Compound A-84 [ka]

[0131] a) Synthesis of intermediate 2-1a Phenylhydrazine hydrochloride (70.0 g, 484.1 mmol) and 7-bromo-3,4-dihydro-2H-naphthalen-1-one (108.9 g, 484.1 mmol) were placed in a round-bottom flask and dissolved in ethanol (1200 mL). 60 mL of hydrochloric acid was slowly added dropwise at room temperature, and the mixture was stirred at 90°C for 12 hours. Upon completion of the reaction, the solvent was removed under reduced pressure, followed by extraction with excess EA. The organic solvent was removed under reduced pressure, and the mixture was stirred with a small amount of methanol and filtered to obtain 95.2 g (66%) of intermediate 2-1a.

[0132] b) Synthesis of intermediate 2-1b Intermediate 2-1a (95.2 g, 319.3 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (108.7 g, 478.9 mmol) were placed in a round-bottom flask and dissolved in toluene (600 ml). The mixture was stirred at 80 °C for 12 hours. After the reaction was completed, the reaction solvent was removed and the product was purified by column chromatography to obtain 41.3 g (44%) of intermediate 2-1b.

[0133] c) Synthesis of intermediate 2-1c Intermediate 2-1b (41.3 g, 139.0 mmol), iodobenzene (199.2 g, 976.0 mmol), CuI (5.31 g, 28.0 mmol), K2CO3 (28.9 g, 209.0 mmol), and 1,10-phenanthroline (5.03 g, 28.0 mmol) were placed in a round-bottom flask and dissolved in DMF (500 mL). The mixture was stirred at 180 °C for 12 hours. After the reaction was complete, the reaction solvent was removed under reduced pressure. The mixture was then dissolved in dichloromethane and filtered through silica gel. After concentrating the dichloromethane, the mixture was recrystallized from hexane to yield 39.0 g (75%) of intermediate 2-1c.

[0134] d) Synthesis of Compound A-84 5.0 g (13.46 mmol) of intermediate 2-1c, 4.41 g (13.46 mmol) of amine intermediate 2-1d, 1.94 g (20.19 mmol) of sodium t-butoxide, and 0.54 g (1.35 mmol) of tri-tert-butylphosphine were dissolved in 100 mL of toluene, and 20.37 g (0.4 mmol) of Pd(dba) was added. The mixture was refluxed under a nitrogen atmosphere for 12 hours. After the reaction was completed, the mixture was extracted with toluene and distilled water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (2:1 volume ratio) to obtain 6.4 g of compound A-84 (82.0% yield).

[0135] Synthesis Example 12: Synthesis of Compound 2-92 [ka]

[0136] a) Synthesis of intermediate 2-92a It was synthesized with reference to the KR10-1423173 B1 patent.

[0137] b) Synthesis of Compound 2-92 5.0 g (16.93 mmol) of intermediate 2-92a, 5.4 g (16.93 mmol) of amine intermediate 2-92b, 2.44 g (25.39 mmol) of sodium t-butoxide, and 0.68 g (1.69 mmol) of tri-tert-butylphosphine were dissolved in 100 mL of toluene, and 0.47 g (0.51 mmol) of Pd(dba) was added. The mixture was refluxed under a nitrogen atmosphere for 12 hours. After the reaction was completed, the organic layer was extracted with toluene and distilled water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (2:1 volume ratio) to obtain 8.2 g of the target compound 2-92 (84.0% yield).

[0138] (Fabrication of organic light-emitting devices) Example 1 An organic light-emitting device having five organic thin film layers was fabricated as follows. The structure was ITO / compound A (1% NDP-9 doping, 1400 Å) / compound B (600 Å) / EML [compound 1: [Ir(piq)2acac] (2 wt%)] (400 Å) / compound C (50 Å) / compound D: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0139] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine Compound B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amine Compound C:2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0140] Example 2, Comparative Example 1 and Comparative Example 2 The devices of Example 2, Comparative Example 1 and Comparative Example 2 were prepared in the same manner as in Example 1, except that the host was changed as shown in Table 2 below.

[0141] Examples 3 to 12 and Comparative Examples 3 to 5 The host was changed as shown in Table 3 below, and the first host and the second host were mixed in a weight ratio of 5:5 to prepare elements of Examples 3 to 12 and Comparative Examples 3 to 5 in the same manner as in Example 1.

[0142] evaluation The luminous efficiency and life characteristics of the organic light-emitting devices according to Examples 1 to 12 and Comparative Examples 1 to 5 were evaluated. The specific measurement methods are as follows, and the results are shown in Tables 2 and 3.

[0143] (1) Measurement of changes in current density due to voltage changes The voltage of the fabricated organic light emitting device was increased from 0 V to 10 V, and the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400). The measured current value was divided by the area to obtain the result.

[0144] (2) Measurement of brightness change due to voltage change The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0145] (3) Luminous efficiency measurement Using the luminance, current density, and voltage measured from (1) and (2), the same current density (10 mA / cm 2 The current efficiency (cd / A) of the

[0146] (4) Measurement of lifespan The organic light-emitting devices manufactured in Examples 1 to 12 and Comparative Examples 1 to 5 were measured for initial luminance (cd / m) using a Polaronics lifespan measurement system. 2 ) to 6,000 cd / m 2 The decrease in brightness over time was measured, and the time point at which the brightness decreased to 95% of the initial brightness was measured as the T95 life.

[0147] The relative values ​​were calculated based on the T95 life of Comparative Examples 1 and 3, and are shown in Tables 2 and 3 below.

[0148] [Table 2]

[0149] [Table 3]

[0150] Referring to Tables 2 and 3, it can be seen that the compounds according to the present invention have improved efficiency and lifetime when used as a single host compared to the comparative compounds. In particular, when combined with a second host, it can be seen that the overall driving voltage, efficiency, and lifetime are significantly improved.

[0151] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made 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. [Explanation of symbols]

[0152] 100, 200, 300, 400 Organic light-emitting devices 105 Organic layer 110 Negative electrode 120 positive electrode 130 Light-emitting layer 140 Hole transport region 150 Electron transport area

Claims

[Claim 1] A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1 below: 【Chemistry 1A】 【Chemistry 1B】 【Chemistry 1C】 【1D】 。

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