Organic optoelectronic elements and display devices

Abstract

The present invention relates to an organic photoelectronic device comprising a positive electrode and a negative electrode facing each other, a light-emitting layer located between the positive electrode and the negative electrode, a hole transport layer located between the positive electrode and the light-emitting layer, and a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, wherein the light-emitting layer comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2; or a combination of chemical formulas 3 and 4, and the hole transport auxiliary layer comprises a third compound represented by the following chemical formula 5. The details of chemical formulas 1 to 5 are defined in the specification.

Description

[Technical Field]

[0001] This invention relates to organic optoelectronic elements and display devices. [Background technology]

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

[0003] Organic optoelectronic devices can be broadly divided into two types according to their operating principle. One type is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transmitted to different electrodes to generate electrical energy. The other type is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of organic optoelectronic devices include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photoconductor drums.

[0005] Among these, organic light-emitting diodes (OLEDs) have attracted considerable attention in recent years due to the increasing demand for flat panel display devices. An organic light-emitting diode is a device that converts electrical energy into light, and its performance is largely influenced by the organic material located between the electrodes. [Overview of the project] [Problems that the invention aims to solve]

[0006] One embodiment of the present invention provides an organic optoelectronic device that can achieve high efficiency characteristics.

[0007] Another embodiment of the present invention provides a display device including the organic optoelectronic element.

Means for Solving the Problem

[0008] According to one embodiment, there is provided an organic optoelectronic device including a positive electrode and a negative electrode facing each other, a light-emitting layer positioned between the positive electrode and the negative electrode, a hole transport layer positioned between the positive electrode and the light-emitting layer, and a hole transport auxiliary layer positioned between the light-emitting layer and the hole transport layer. The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2 or a combination of the following Chemical Formulas 3 and 4, and the hole transport auxiliary layer includes a third compound represented by the following Chemical Formula 5.

Chem.

Chem.

[0009] According to another embodiment, a display device including the organic photoelectron element is provided. [Effects of the Invention]

[0010] This invention makes it possible to realize organic optoelectronic devices with high efficiency characteristics. [Brief explanation of the drawing]

[0011] [Figure 1] This is a cross-sectional view showing an organic light-emitting element according to one embodiment. [Modes for carrying out the invention]

[0012] Embodiments of the present invention will be described in detail below. However, these are presented as examples only, and the present invention is not limited thereto, but is defined solely within the scope of the claims described later.

[0013] In this specification, "substituted" means that, unless otherwise defined, at least one hydrogen atom of a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C30 amine group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0014] In one example of the present invention, "substitution" means that at least one hydrogen atom of the substituent or compound is substituted with deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen atom of the substituent or compound is substituted with deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen atom of the substituent or compound is substituted with deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen atom of the substituent or compound is substituted 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.

[0015] In this specification, "unsubstituted" means that the hydrogen atom remains as a hydrogen atom without being replaced by another substituent.

[0016] In this specification, "hydrogen (-H)" may include "deuterium-substituted (-D)" or "tritium-substituted (-T)".

[0017] In this specification, "hetero" means, unless otherwise defined, a functional group containing one to three heteroatoms selected from the group consisting of N, O, S, P, and Si, with the remainder being carbon.

[0018] In this specification, "aryl group" is a general concept encompassing groups having one or more hydrocarbon aromatic molecules, and includes forms in which all elements of the hydrocarbon aromatic molecule have p-orbitals, and these p-orbitals form conjugation, such as phenyl groups and naphthyl groups; forms in which two or more hydrocarbon aromatic molecules are linked by sigma bonds, such as biphenyl groups, terphenyl groups, and quarterphenyl groups; and non-aromatic condensed rings formed by the direct or indirect condensation of two or more hydrocarbon aromatic molecules, such as fluorenyl groups.

[0019] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0020] In this specification, “heterocyclic group” is a broader concept including heteroaryl groups, and means a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, that contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C). If the heterocyclic group is a fused ring, the entire heterocyclic group or each of the rings may contain one or more heteroatoms.

[0021] For example, a "heteroaryl group" means that the aryl group contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups can be directly bonded by sigma bonds, or, if the heteroaryl group contains two or more rings, the two or more rings can be fused together. If the heteroaryl group is a fused ring, each ring can contain one to three of the heteroatoms.

[0022] More specifically, substituted or unsubstituted C6-C30 aryl groups may be, but are not limited to, substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracenyl groups, substituted or unsubstituted phenantrenyl groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted p-terphenyl groups, substituted or unsubstituted m-terphenyl groups, substituted or unsubstituted o-terphenyl groups, substituted or unsubstituted chrysenyl groups, substituted or unsubstituted triphenylene groups, substituted or unsubstituted perilennyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted indenyl groups, or combinations thereof.

[0023] More specifically, substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms include substituted or unsubstituted furanyl groups, substituted or unsubstituted thiophenyl groups, substituted or unsubstituted pyrrolyl groups, substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted imidazolyl groups, substituted or unsubstituted triazolyl groups, substituted or unsubstituted oxazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted thiadiazolyl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted pyrimidinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted triazinyl groups, substituted or unsubstituted benzofuranyl groups, substituted or unsubstituted benzothiophenyl groups, and substituted or unsubstituted This may include, but is not limited to, a benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthilidinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiadinyl 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.

[0024] In this specification, hole properties refer to the property of being able to donate electrons and form holes when an electric field is applied, having conductivity properties according to the HOMO level, and facilitating the injection of holes formed at the positive electrode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the positive electrode, and movement within the light-emitting layer.

[0025] Furthermore, electronic properties refer to the characteristics that allow electrons to be received when an electric field is applied, possessing conductivity characteristics according to the LUMO level, and facilitating the injection of electrons formed at the negative electrode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the negative electrode, and movement within the light-emitting layer.

[0026] The following describes an organic optoelectronic device according to one embodiment.

[0027] Organic photoelectronic devices are not particularly limited as long as they are devices that can convert electrical energy and light energy into each other, and examples include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photoreceptor drums.

[0028] Here, we will explain using an organic light-emitting device, which is an example of an organic optoelectronic device, as an example, but the explanation is not limited to this and can be applied similarly to other organic optoelectronic devices.

[0029] In the drawings, the thickness is enlarged to clearly represent multiple layers and regions. Similar parts throughout the specification are given the same reference numeral. When a part such as a layer, film, region, or plate is said to be "on top of" another part, this includes not only when it is "directly on top of" another part, but also when there is another part in between. Conversely, when a part is said to be "directly on top of" another part, it means that there is no other part in between.

[0030] Figure 1 is a schematic cross-sectional view showing an organic optoelectronic device according to one embodiment.

[0031] Referring to Figure 1, an organic optoelectronic element according to one embodiment includes a positive electrode 10 and a negative electrode 20 facing each other, and an organic layer 30 located between the positive electrode 10 and the negative electrode 20.

[0032] The positive electrode 10 is made of a conductor with a high work function so that hole injection can proceed smoothly, for example, a metal, a metal oxide and / or a conductive polymer. Examples of materials for the positive electrode 10 include, but are not limited to, metals or alloys thereof such as nickel, platinum, vanadium, chromium, copper, zinc, and gold; 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 SnO2 and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (poly(ethylene-1,2-dioxy)thiophene: PEDOT), polypyrrole and polyaniline.

[0033] The negative electrode 20 is made of a conductor with a low work function, for example, to allow electron injection to proceed smoothly, and is made of metals, metal oxides and / or conductive polymers. Examples of materials that make up the negative electrode 20 include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium; and multilayer materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca.

[0034] The organic layer 30 includes a hole transport layer 31, a light-emitting layer 32, and a hole transport auxiliary layer 33 located between the hole transport layer 31 and the light-emitting layer 32.

[0035] The hole transport layer 31 is a layer that facilitates hole transfer from the positive electrode 10 to the light-emitting layer 32, and may, for example, be an amine compound, but is not limited thereto.

[0036] The amine compound may, for example, contain at least one aryl group and / or heteroaryl group. The amine compound may, for example, be represented by the following chemical formula a or chemical formula b, but is not limited to these. [ka]

[0037] In the aforementioned chemical formula a or b, Ar a ~Ar g Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof. Ar a ~Ar c At least one of and Ar d ~Ar g At least one of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a combination thereof. Ar h These are single-bonded, substituted or unsubstituted alkylene groups with 1 to 20 carbon atoms, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups with 2 to 30 carbon atoms, or combinations thereof.

[0038] The light-emitting layer 32 includes at least two types of host and dopant, wherein the host includes a first compound having relatively strong bipolar properties and a second compound having relatively strong hole properties.

[0039] The first compound is a compound having relatively strong bipolar properties in its electronic characteristics, and is represented by the following chemical formula 1. [ka]

[0040] In the above chemical formula 1, Z 1 ~Z 3 Each of these can be independently N or CR a And, Z 1 ~Z 3At least two of them are N, R 1 ~R 8 and R a Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. L 1 ~L 3 Each of these is independently a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms. Ar 1 and Ar 2 These are, independently, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic groups with 2 to 30 carbon atoms.

[0041] The first compound has a structure in which at least one 9-carbazole is substituted on a pyrimidine or triazine ring, which allows it to readily accept electrons when an electric field is applied. Therefore, together with the second compound described later, it can achieve good interfacial properties and appropriately adjust the flow of holes and electrons, thereby improving the driving voltage of the organic optoelectronic device to which the first compound is applied.

[0042] In the above chemical formula 1, Ar 1 and Ar 2 Each of these groups can 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 phenantrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

[0043] As an example, the Ar 1 and Ar 2Each of these groups can independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

[0044] In the above chemical formula 1, L 1 ~L 3 Each of these can independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0045] For example, L 1 -Ar 1 and L 2 -Ar 2 Each substituent is independently selected from among the substituents listed in Group I below. [Group I] [ka]

[0046] Among the aforementioned group I, R 46 ~R 48 Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m6 is one of the integers from 1 to 5. m7 is one of the integers from 1 to 4. m8 is one of the integers between 1 and 3. * represents the bonding site.

[0047] In the above chemical formula 1, R 1 ~R 8Each of these can independently be hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0048] As an example, R 1 ~R 8 Each of these can independently be hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0049] In the above chemical formula 1, R a This can be hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0050] As an example, R a This can be hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0051] The first compound may, for example, be one selected from the compounds listed in Group 1 below, but is not limited to these. [Group 1] [ka] [ka] [ka] [ka] [ka] [ka]

[0052] The first compound can be one or more types.

[0053] The second compound can be used in the light-emitting layer together with the first compound to enhance charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics.

[0054] The second compound is represented, for example, by the following chemical formula 2. [ka]

[0055] In the aforementioned chemical formula 2, Ar 3 and Ar 4 Each of these is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. L 4 and L 5 Each of these is independently a single-bonded, substituted, or unsubstituted arylene group with 6 to 20 carbon atoms. R 9 ~R 19 Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m1 and m2 are each independently one of the integers between 1 and 3. m3 is one of the integers from 1 to 4. n is one of the integers between 0 and 2.

[0056] When m1 is 2 or more, each R 13 may be the same as or different from each other.

[0057] When m2 is 2 or more, each R 14 may be the same as or different from each other.

[0058] When m3 is 2 or more, each R 19 may be the same as or different from each other.

[0059] As an example, Ar 3 and Ar 4 in the chemical formula 2 are each independently 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 anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, L 4 and L 5 in the chemical formula 2 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R 9 ~R 19 in the chemical formula 2 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n can be 0 or 1.

[0060] As an example, "substituted" in the chemical formula 2 means that at least one hydrogen is substituted with deuterium, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

[0061] In a specific embodiment of the present invention, the chemical formula 2 is represented by one of the following chemical formulas 2-1 to 2-15. [Chemical formula]

[0062] In the above Chemical formulas 2-1 to 2-15, R 9 ~R 19 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, m1 and m2 are each independently one of the integers from 1 to 3, m3 is one of the integers from 1 to 4, L 4 -Ar 3 and L 5 -Ar 4 can each independently be one of the substituents listed in Group II below. [Group II] [Chemical formula]

[0063] In the above Group II, R 49 ~R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, m9 is one of the integers from 1 to 5, m10 is one of the integers from 1 to 4, m11 is one of the integers from 1 to 3, m12 is an integer of 1 or 2, * is the bonding position.

[0064] When m9 is 2 or more, each R 49 may be the same as or different from each other.

[0065] When m10 is 2 or more, each R 50 may be the same as or different from each other.

[0066] If m11 is 2 or more, each R 51 They may be the same or different from one another.

[0067] If m12 is 2 or more, each R 52 They may be the same or different from one another.

[0068] In one embodiment, the chemical formula 2 is represented by the chemical formula 2-8.

[0069] Also, L in the above chemical formula 2-8 4 -Ar 3 and L 5 -Ar 4 Each of these can be independently selected from Group II, and may be, for example, any one of E-1, E-2, E-3, E-4, E-7, E-8, and E-9.

[0070] The second compound can be represented, for example, by a combination of chemical formulas 3 and 4 below. [ka]

[0071] In the aforementioned chemical formulas 3 and 4, Ar 5 and Ar 6 Each of these is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. a1 in chemical formula 3 * ~a4 * Each of these is independently a bonded carbon (C) or CL. a -R b And, In chemical formula 4 * Each of these is independently a bonded carbon (C), a1 in chemical formula 3 * ~a4 * Two of the adjacent ones are in chemical formula 4 * It is combined with, L a , L6 and L 7 Each of these is independently a single-bonded, substituted, or unsubstituted arylene group with 6 to 20 carbon atoms. R b and R 20 ~R 27 Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.

[0072] As an example, the second compound represented by the combination of chemical formulas 3 and 4 can be represented by any one of the following chemical formulas: 3A, 3B, 3C, 3D, and 3E. [ka]

[0073] In the chemical formulas 3A to 3E, Ar 5 Ar 6 , L 6 , L 7 , and R 20 ~R 27 As stated above, L a1 ~L a4 The above is L 6 and L 7 As defined above, R a1 ~R a4 The above is R 20 ~R 27 As defined above.

[0074] For example, Ar in chemical formulas 3 and 4 5 and Ar 6 Each of these is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R a1 ~R a4 and R 20 ~R 27 Each of these can independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0075] In one specific embodiment of the present invention, L in chemical formulas 3 and 4 6 -Ar 5 and L 7 -Ar 6 Each of these can be independently selected from the substituents listed in Group II.

[0076] In one embodiment, the R a1 ~R a4 and R 20 ~R 27 Each of these can independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0077] For example, the R a1 ~R a4 and R 20 ~R 27 Each of these is independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group. In one specific embodiment, the R a1 ~R a4 , and R 20 ~R 27 Each of these can independently be hydrogen, deuterium, or a phenyl group.

[0078] For example, the compound for the second organic optoelectronic device may be, but is not limited to, one of the compounds listed in Group 2 below. [Group 2] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0079] Furthermore, examples of forms in which at least one hydrogen atom is substituted with deuterium in compounds B-1 to B-152 listed in Group 2 are shown below, but are not limited to these examples. [ka] [ka]

[0080] The following examples merely present the most specific structures of compounds B-153 to B-197 in Group 2, based on their deuterium substitution positions and substitution ratios, and there is no intention to limit the scope of rights for compounds not presented below.

[0081] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds shown below, and the deuterium substitution position and deuterium substitution rate can include all modifiable ranges within the range of compounds B-1 to B-197. [ka] [ka] [ka] [ka] [ka] [ka]

[0082] Furthermore, examples of forms in which at least one hydrogen atom is substituted with deuterium in compounds C-1 to C-57 listed in Group 2 are shown below, but are not limited to these examples. [ka]

[0083] The following examples merely present the most specific structures of compounds C-58 to C-72 in the aforementioned group, based on their deuterium substitution positions and substitution ratios, and there is no intention to limit the scope of rights for compounds not presented below.

[0084] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds shown below, and the deuterium substitution position and deuterium substitution rate can include all modifiable ranges within the range of compounds C-1 to C-72. [ka] [ka]

[0085] The second compound can be used in the form of one or more types.

[0086] The first compound and the second compound can be included as hosts in the light-emitting layer 32, for example, in a weight ratio of about 1:99 to 99:1. By including them within the above range, the electron transport capability of the first compound and the hole transport capability of the second compound can be utilized to achieve bipolar characteristics by matching the appropriate weight ratio, thereby improving efficiency and lifetime. Within the above range, for example, they can be included in weight ratios of about 10:90 to 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50. As a specific example, they can be included in weight ratios of 20:80, 30:70, or 40:60.

[0087] The light-emitting layer 32 may further contain one or more compounds as a host, in addition to the first and second compounds described above.

[0088] The light-emitting layer 32 may further contain a dopant.

[0089] The dopant may be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0090] A dopant is a substance that is mixed in small amounts with a compound for organic optoelectronic devices to induce light emission. Generally, substances such as metal complexes that emit light through multiple excitation (excitation to a triplet state or higher) can be used. Dopants can be inorganic, organic, or organic-inorganic compounds, and may consist of one or more types.

[0091] Examples of dopants include phosphorescent dopants, which include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the following chemical formula Z, but are not limited to these. [Chemical formula Z] L 9 MX 1

[0092] In the aforementioned chemical formula Z, M is a metal, and L 9 and X 1 These are ligands that are either identical or different from each other and form complex compounds with M.

[0093] The aforementioned M is, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the aforementioned L 9 and X 1 For example, this could be a Bidentate ligand.

[0094] L 9 and X 1 Examples of ligands represented by can be selected from, but are not limited to, the chemical formulas listed in Group A below. [Group A] [ka]

[0095] Among the aforementioned group A, R 300 ~R 302 Each of these is independently a C1-C30 alkyl group that is substituted or unsubstituted with hydrogen, deuterium, or halogen, or an aryl group or halogen that is substituted or unsubstituted with an alkyl group having 1-C30 atoms. R 303 ~R 324 Each of these is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C1-C30 heteroaryl group, substituted or unsubstituted C1-C30 amino group, substituted or unsubstituted C6-C30 arylamino group, SF5, trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0096] The dopant according to one embodiment is an iridium complex, represented, for example, by the following chemical formula V-1 or chemical formula V-2.

[0097] [ka]

[0098] In the aforementioned chemical formula V-1, R 101 ~R 116 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 And, The aforementioned R 132 ~R 134Each of these is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R 101 ~R 116 At least one of them is a functional group represented by the following chemical formula 6, L 100 It is a monovalent anionic bidentate ligand that coordinates to iridium via a lone pair of electrons on a carbon or heteroatom. n5 and n6 are independent integers between 0 and 3, and n5 + n6 is an integer between 1 and 3. [ka] In the aforementioned chemical formula 6, R 135 ~R 139 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 And, * This refers to the part that is bonded to a carbon atom.

[0099] [ka]

[0100] In the aforementioned chemical formula V-2, R 101 ~R 117 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 And, The aforementioned R 133 ~R 135 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. L 100is a monovalent anion bidentate ligand that coordinates to iridium via non-shared electron pairs of carbon or heteroatoms. n1 and n2 are each independently any one of the integers from 0 to 3, and n1 + n2 is any one of the integers from 1 to 3.

[0101] The dopant according to another embodiment is a platinum complex, for example, represented by the following chemical formula Z-1.

Chemical formula

[0102] In the chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring; R A 、R B 、R C 、and R D each independently represent mono-substituted, di-substituted, tri-substituted, tetra-substituted, or unsubstituted; L B 、L C 、and L D are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR’, SiRR’, GeRR’, and combinations thereof; When nA is 1, L E is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR’, SiRR’, GeRR’, and combinations thereof; when nA is 0, L E does not exist; R A 、R B 、R C 、R DR, and R' are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphinone group, and any combination thereof; any adjacent R A , R B , R C , R D R, R', and R' can be optionally joined to form a ring; X B , X C , X D , and X E Each is independently selected from the group consisting of carbon and nitrogen; Q 1 Q 2 Q 3 , and Q 4 Each of these represents either oxygen or a direct bond.

[0103] The dopant according to one embodiment is a platinum complex, represented, for example, by the following chemical formula VI-1 or chemical formula VI-2. [ka]

[0104] In the aforementioned chemical formulas VI-1 and VI-2, X 100 O, S and NR 132 Selected from among, R 118 ~R 132 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 And, The aforementioned R 133 ~R 135Each of these is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R 118 ~R 132 At least one of them is -SiR 133 R 134 R 135 Alternatively, it is a tert-butyl group.

[0105] The hole transport auxiliary layer 33 contains a third compound having bipolar properties with relatively strong hole characteristics.

[0106] As described above, the light-emitting layer 32 contains a first compound having relatively strong bipolar characteristics and a second compound having relatively strong hole characteristics. Compared to when these compounds are used alone, this enhances the mobility of electrons and holes, and significantly improves the luminescence efficiency.

[0107] In devices where a material with an unbalanced electronic or hole property is introduced into the light-emitting layer, carrier recombination occurs at the interface between the light-emitting layer and the electron or charge transport layer, resulting in a relatively high rate of exciton formation. As a result, a roll-off phenomenon occurs where efficiency drops sharply due to the interaction between charges at the interface between molecular excitons in the light-emitting layer and the hole transport layer, and the luminescence lifetime also drops sharply.

[0108] To solve these problems, by simultaneously introducing the first and second compounds into the light-emitting layer to prevent the light-emitting region from being biased towards either the electron transport layer or the hole transport layer, and further including a hole transport auxiliary layer containing a third compound with relatively strong hole properties between the hole transport layer and the light-emitting layer, it is possible to fabricate a device that prevents charge accumulation at the interface between the hole transport layer and the light-emitting layer and balances the carriers within the light-emitting layer. This improves the roll-off characteristics of the organic optoelectronic device and significantly improves its lifetime characteristics.

[0109] The third compound is represented by the following chemical formula 5. [ka]

[0110] In the above Chemical Formula 5, Ar 8 and Ar 9 are each independently 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, the above Ar 10 and Ar 11 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 41 ~R 45 are each independently hydrogen, deuterium, a cyano group, a halogen 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, m5 is one of the integers from 1 to 3.

[0111] When m5 is 2 or more, each R 41 may be the same as or different from each other.

[0112] The third compound has a structure in which at least one fluorene group is substituted on an amine core.

[0113] By substituting at least one fluorene group on the amine core, deterioration and decomposition due to reduction of the deposition temperature can be minimized due to steric hindrance, and thus the lifetime characteristics can be further improved.

[0114] As an example, the third compound is represented by any one of the following Chemical Formulas 5-1 to 5-4, depending on the substitution position of fluorene.

Chemical Formula

[0115] In the above Chemical Formulas 5-1 to 5-4, Ar 8 ~Ar11 , R 41 ~R 45 The definition of m5 is as described above.

[0116] As an example, the third compound is represented by the chemical formula 5-4.

[0117] In the aforementioned chemical formula 5, Ar 8 and Ar 9 Each of these groups can independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0118] As an example, the Ar 8 and Ar 9 Each of these can independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0119] In the aforementioned chemical formula 5, Ar 10 and Ar 11 Each of these can independently be a substituted or unsubstituted C1-C5 alkyl group or a substituted or unsubstituted C6-C12 aryl group.

[0120] As an example, the Ar 10 and Ar 11 Each of these can independently be a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0121] In the above chemical formula 5, R 41 ~R 45 Each of these can independently be hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0122] As an example, R41 ~R 45 Each of these can independently be hydrogen, deuterium, or a tert-butyl group.

[0123] The aforementioned Ar 8 and Ar 9 At least one of these is a substituted or unsubstituted fluorenyl group, represented, for example, by the chemical formula 5-4-1 below. [ka]

[0124] In the aforementioned chemical formula 5-4-1, Ar 9 ~Ar 11 , R 41 ~R 45 And the definition of m5 is as described above. Ar 12 and Ar 13 Each of these is 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 53 ~R 57 Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m13 is one of the integers between 1 and 3.

[0125] In the aforementioned chemical formula 5-4-1, if m13 is 2 or more, each R 53 They may be the same or different from one another.

[0126] In the aforementioned chemical formula 5-4-1, Ar 12 and Ar 13 Each of these can independently be a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0127] As an example, the Ar 12and Ar 13 Each of these can independently be a substituted or unsubstituted C1-C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0128] In the above chemical formula 5-4-1, R 53 ~R 57 Each of these can independently be hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0129] As an example, R 53 ~R 57 Each of these can independently be hydrogen, deuterium, or a tert-butyl group.

[0130] As a more specific example, the aforementioned chemical formula 5-4-1 is selected from the following chemical formulas 5-4-1a, 5-4-1b, 5-4-1c, and 5-4-1d. [ka]

[0131] In the aforementioned chemical formulas 5-4-1a, 5-4-1b, 5-4-1c, and 5-4-1d, Ar 9 ~Ar 13 , R 41 ~R 45 , R 53 ~R 57 The definitions of m5 and m13 are as described above.

[0132] As a most specific example, the third compound is represented by the chemical formula 5-4-1b.

[0133] As an example, R in the above chemical formula 5 42 ~R 45 At least two of these may be tert-butyl groups.

[0134] Heat resistance can be improved by introducing alkyl groups that can increase the glass transition temperature.

[0135] As a specific example, R in the chemical formula 5-4-1 42 ~R 45 At least two of the above or R 54 ~R 57 At least two of these may be tert-butyl groups.

[0136] For example, R in the chemical formula 5 43 and R 45 Each of these can be a tert-butyl group.

[0137] For example, R in the chemical formula 5-4-1 43 and R 45 Each of these can be a tert-butyl group.

[0138] For example, R in the chemical formula 5-4-1 54 and R 56 Each of these can be a tert-butyl group.

[0139] For example, the third compound may be, but is not limited to, one of the compounds listed in Group 3 below. [Group 3] [ka] [ka] [ka] [ka]

[0140] In one of the most specific embodiments of the present invention, the first compound is represented by chemical formula 1, the second compound is represented by chemical formula 2-8 or chemical formula 3C, and the third compound is represented by chemical formula 5-4-1b.

[0141] Furthermore, the organic layer 30 may further include an electron transport region.

[0142] The electron transport region can further enhance electron injection and / or electron mobility between the negative electrode 20 and the light-emitting layer 32, and can block holes.

[0143] Specifically, the electron transport region may include an electron transport layer between the negative electrode 20 and the light-emitting layer 32, and an electron transport auxiliary layer between the light-emitting layer 32 and the electron transport layer 34, and at least one of the compounds listed in Group B below may be included in at least one of the electron transport layer and the electron transport auxiliary layer. [Group B] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0144] On the other hand, an organic light-emitting device may also include, in addition to the light-emitting layer, an electron injection layer (not shown), a hole injection layer (not shown), and the like as the organic layers described above.

[0145] Organic light-emitting diodes can be manufactured by first forming a positive or negative electrode on a substrate, then forming an organic layer using a dry deposition method such as vacuum deposition, sputtering, plasma plating, or ion plating, and finally forming the negative or positive electrode on top of that.

[0146] The organic light-emitting element described above can be applied to an organic light-emitting display device.

[0147] The embodiments described above will be explained in more detail below through the examples provided. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0148] In the following examples and synthesis examples, the starting materials and reactants used were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods, unless otherwise specified.

[0149] As a more specific example of the compounds of the present invention, the compounds presented were synthesized in the following steps.

[0150] Synthesis of the first compound Synthesis Example 1: Synthesis of Compound A-43 [ka]

[0151] Step 1: Synthesis of intermediate Int-1 2,4-Dichloro-6-phenyl-1,3,5-triazine (20.0 g, 88.5 mmol), 3-dibenzofuranylboronic acid (17.8 g, 84.1 mmol), K2CO3 (24.5 g, 176.9 mmol), and Pd(dppf)Cl2 (3.6 g, 4.4 mmol) were placed in a round-bottom flask and dissolved in Toluene (250 ml) and distilled water (90 ml). The mixture was then stirred at 60°C for 6 hours. After the reaction was complete, the aqueous layer was separated using a fractionation funnel, and the organic layer was distilled under reduced pressure. The mixture was heated and dissolved in monochlorobenzene, and recrystallized through a silica filter to obtain 14.4 g (48%) of the intermediate Int-1.

[0152] Two steps: Synthesis of intermediate Int-2 Intermediate Int-1 (14.4 g, 40.2 mmol), 5-Chloro-2-fluorophenylboronic acid (6.8 g, 39.0 mmol), K2CO3 (10.8 g, 78.0 mmol), and Pd(PPh3)4 (2.25 g, 1.95 mmol) were placed in a round-bottom flask, dissolved in THF (180 ml) and distilled water (40 ml), and then stirred under reflux at 55°C for 6 hours. After the reaction was complete, the aqueous layer was removed, and 13.2 g (75%) of intermediate Int-2 was obtained by column chromatography (Hexane: DCM (30%)).

[0153] 3 steps: Synthesis of intermediate Int-3 Intermediate Int-2 (13.2 g, 29.2 mmol), phenylboronic acid (10.7 g, 86.6 mmol), Cs2CO3 (19.0 g, 58.4 mmol), tri-tert-butylphosphine (2.9 ml, 5.8 mmol), and Pd2(dba)3 (1.3 g, 1.5 mmol) were placed in a round-bottom flask and dissolved in 1,4-Dioxane (120 ml). The mixture was then stirred under reflux at 100°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reactants were poured into excess methanol to precipitate the solid. The solid was then filtered, and recrystallized with monochlorobenzene to obtain 10.8 g (75%) of intermediate Int-3.

[0154] Step 4: Synthesis of compound A-43 Intermediate Int-3 (10.8 g, 21.9 mmol), 2-Phenyl-9H-carbazole (6.4 g, 26.3 mmol), and K3PO4 (9.3 g, 43.8 mmol) were placed in a round-bottom flask, dissolved in DMF (100 ml), and then stirred under reflux at 150°C for 4 hours. After the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate the solid, and the resulting solid was filtered and recrystallized with Toluene to obtain 12.6 g (80%) of compound A-43.

[0155] Synthesis Example 2: Synthesis of Compound A-44 [ka]

[0156] Step 1: Synthesis of intermediate Int-5 Using 2,4-Dichloro-6-phenyl-1,3,5-triazine (30.0 g, 132.7 mmol), intermediate Int-4 (46.7 g, 126.1 mmol), K2CO3 (36.7 g, 265.4 mmol), and Pd(dppf)Cl2 (5.42 g, 6.64 mmol), intermediate Int-5 was synthesized in the same one-step manner as in Synthesis Example 1 to obtain 45.6 g (83%).

[0157] Two steps: Synthesis of intermediate Int-6 1-Bromo-3-chloro-2-fluorobenzene (25.0 g, 119.4 mmol), phenylboronic acid (16.0 g, 131.3 mmol), K2CO3 (33.0 g, 238.7 mmol), and Pd(PPh3)4 (6.9 g, 6.0 mmol) were placed in a round-bottom flask, dissolved in THF (350 ml) and distilled water (120 ml), and then stirred under reflux at 65°C for 6 hours. After the reaction was complete, the aqueous layer was removed, and 21.7 g (88%) of the intermediate Int-6 was obtained by column chromatography (Hexane: DCM (20%)).

[0158] 3 steps: Synthesis of intermediate Int-7 Intermediate Int-6 (21.7g, 105.0 mmol), Bis(pinacolato)diboron (32.0g, 126.0 mmol), Tricyclohexylphosphine (5.1g, 21.0 mmol), Potassium acetate (20.6g, 210.0 mmol), and Pd(dppf)Cl2 (4.29g, 5.25 mmol) were placed in a round-bottom flask and dissolved in 250 ml of DMF. The mixture was stirred under reflux at 140°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove the salts, and then extracted with excess DCM and distilled water. 25.1 g (80%) of intermediate Int-7 was obtained by column chromatography (Hexane:DCM (30% to 50%)).

[0159] 4 steps: Synthesis of intermediate Int-8 Intermediate Int-5 (14.5g, 33.4 mmol), intermediate Int-7 (11.0g, 36.8 mmol), K2CO3 (9.2g, 66.8 mmol), and Pd(PPh3)4 (1.93g, 1.67 mmol) were placed in a round-bottom flask, dissolved in THF (170 ml) and distilled water (40 ml), and then stirred under reflux at 70°C for 6 hours. After the reaction was complete, the aqueous layer was removed, and 13.3 g (70%) of intermediate Int-8 was obtained by column chromatography (Hexane: DCM (30%)).

[0160] Step 5: Synthesis of Compound A-44 The intermediates Int-8 (13.3 g, 23.4 mmol), 9H-Carbazole (4.7 g, 28.0 mmol), and K3PO4 (9.9 g, 46.7 mmol) were placed in a round-bottom flask, dissolved in DMF (100 ml), and then stirred under reflux at 150°C for 4 hours. After the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate the solid, and the resulting solid was filtered and recrystallized with monochlorobenzene to obtain 14.1 g (84%) of compound A-44.

[0161] Synthesis Example 3: Synthesis of Compound A-77 [ka]

[0162] Compound A-77 was synthesized using the intermediate Int-9 (CAS No. 1642330-72-0) and 2-Phenyl-9H-carbazole in the same four-step manner as in Synthesis Example 1.

[0163] Synthesis Example 4: Synthesis of Compound A-90 [ka]

[0164] Compound A-90 was synthesized using intermediate Int-10 (CAS No. 2745196-22-7) and intermediate Int-11 (CAS No. 1189047-28-6) in the same one-step manner as in Synthesis Example 1.

[0165] Comparative Synthesis Example 1: Synthesis of Compound Host-1 [ka]

[0166] Compound Host-1 was synthesized by referring to the synthesis method publicly known in publication WO2023 / 072977.

[0167] Synthesis of the second compound Synthesis Example 5: Synthesis of Compound B-136 [ka]

[0168] Compound B-136 was synthesized by referring to the synthesis method publicly known in US Patent 10476008 B2.

[0169] HRMS(70eV, EI+):m / z calcd for C42H28N2:560.2252, found:560. Elemental Analysis: C, 90%; H, 5%

[0170] Synthesis of the third compound Synthesis Example 6: Synthesis of Compound E-1 [ka]

[0171] 410 g (1.203 mol) of intermediate E-1-1 (CAS No. 2924473-03-8), 435 g (1.082 mol) of amine intermediate (CAS No. 897674-69-1), and 173 g (1.804 mol) of sodium t-butoxide were placed in a round-bottom flask and dissolved in 4000 ml of toluene. 355 g (0.06 mol) of Pd2 (dba) and 74 g (0.18 mol) of S-phos were added sequentially, and the mixture was stirred under reflux under a nitrogen atmosphere for 6 hours. After the reaction was complete, the toluene solvent was removed, and the mixture was extracted with toluene and distilled water. The organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was recrystallized and purified with n-hexane / methanol to obtain 600 g (71% yield) of compound E-1.

[0172] Synthesis Example 7: Synthesis of Compound E-21 [ka]

[0173] Compound E-21 was synthesized using intermediate E-1-1 and the amine intermediate (CAS NO. 500717-23-7) in the same manner as the synthesis method in Synthesis Example 6.

[0174] (Fabrication of organic light-emitting devices) Example 1 A glass substrate coated with a thin film of ITO (Indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After that, it was transferred to a plasma cleaning apparatus, where it was cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition apparatus. Using the ITO transparent electrode prepared in this way as the positive electrode, compound A doped with 3% NDP-9 (Novaled) was vacuum deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å. Compound A was then deposited on top of the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound E-21 obtained in Synthesis Example 8 was deposited on top of the hole transport layer to a thickness of 270 Å to form a first hole transport auxiliary layer, and compound B was deposited on top of the first hole transport auxiliary layer to a thickness of 50 Å to form a second hole transport auxiliary layer. A 380 Å thick light-emitting layer was formed by vacuum deposition on top of the second hole transport auxiliary layer using 85 wt% of compound A-43 (40%) synthesized in Synthesis Example 1 and compound B-136 (60%) synthesized in Synthesis Example 5 as hosts, and doping with 15 wt% of PtGD as a dopant. Next, compound C was deposited to a thickness of 50 Å on top of the light-emitting layer to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum-deposited in a 1:1 weight ratio to form an electron transport layer with a thickness of 310 Å. An organic light-emitting device was fabricated by sequentially vacuum-depositing Yb 15 Å and Al 1200 Å on top of the electron transport layer to form a negative electrode.

[0175] The device was fabricated with the following structure: ITO / Compound A (3% NDP-9 doping, 100 Å) / Compound A (1350 Å) / First hole transport auxiliary layer (270 Å) / Compound B (50 Å) / Emitting layer [Host (Compound A-43:Compound B-136=40:60):PtGD=85 wt%:15 wt%] (380 Å) / Compound C (50 Å) / Compound D:Liq (310 Å) / Yb (15 Å) / Al (1200 Å).

[0176] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine Compound B: 9,9-dimethyl-N-[3-(9-phenyl-9H-fouoren-9-yl)phenyl]-N-(4-phenylphenyl)-9H-fluoren-2-amine Compound C:4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-2-yl}phenyl)-4,6-diphenyl-1,3,5-triazine PtGD: [ka]

[0177] Examples 2-4 and Comparative Example 1 Except for changing the host as described in Table 1 below, the elements of Examples 2-4 and Comparative Example 1 were fabricated in the same manner as in Example 1.

[0178] evaluation The luminous efficiency characteristics of the organic light-emitting devices in Examples 1-4 and Comparative Example 1 were evaluated.

[0179] The specific measurement method is as follows, and the results are shown in Table 1. (1) Measurement of the change in current density in response to voltage changes For the manufactured organic light-emitting diodes, the voltage was increased from 0V to 10V while measuring the current flowing through each unit element using a current-voltmeter (Keithley 2400). The measured current values ​​were then divided by the area to obtain the results. (2) Measurement of brightness change in response to voltage change The brightness of the manufactured organic light-emitting diode was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained. (3) Measurement of luminous efficiency Using the brightness, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) was used. 2 The current efficiency (cd / A) was calculated.

[0180] The luminous efficiency values ​​for Examples 1-4 and Comparative Example 1 were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1 below. [Table 1]

[0181] Referring to Table 1, it can be confirmed that the organic light-emitting device to which the composition according to the embodiment of the present invention was applied showed a significant improvement in luminous efficiency compared to the organic light-emitting device according to the comparative example.

[0182] Although 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, utilizing the basic concepts of the present invention as defined in the claims, also fall within the scope of the present invention. [Explanation of Symbols]

[0183] 10 positive electrode 20 negative electrode 30 organic layer 31 Hole transport layer 32. Emitting layer 33 Hole transport auxiliary layer 34 Electron transport layer

Claims

1. The positive and negative poles facing each other, A light-emitting layer located between the positive electrode and the negative electrode, A hole transport layer located between the positive electrode and the light-emitting layer, and It includes a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, The light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2; or a combination of the following chemical formulas 3 and 4. The hole transport auxiliary layer comprises a third compound represented by the following chemical formula 5, in an organic optoelectronic device: 【Chemistry 1】 In the aforementioned chemical formula 1, Z １ ~Z ３ Each is independently N or CR ａ And, Z １ ~Z ３ At least two of them are N, R １ ~R ８ and R ａ Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. L １ to L ３ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, Ar １ and Ar ２ Each of these is independently 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; 【Chemistry 2】 In the aforementioned chemical formula 2, Ar ３ and Ar ４ Each of these is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. L ４ and L ５ Each of these is independently a single-bonded, substituted, or unsubstituted arylene group having 6 to 20 carbon atoms. R ９ ~R １９ Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m1 and m2 are each independently one of the integers from 1 to 3. m3 is one of the integers from 1 to 4. n is one of the integers between 0 and 2; 【Transformation 3】 In the aforementioned chemical formulas 3 and 4, Ar ５ and Ar ６ Each of these is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. a in chemical formula 3 １ ＊ ~a ４ ＊ Each of these is independently a bonded carbon (C) or C-L ａ -R ｂ And, In chemical formula 4 ＊ Each of these is independently a bonded carbon (C), a in chemical formula 3 １ ＊ ~a ４ ＊ Two of the adjacent ones are in chemical formula 4 ＊ It is combined with, L ａ , L ６ and L ７ Each of these is independently a single-bonded, substituted, or unsubstituted arylene group having 6 to 20 carbon atoms. R ｂ and R ２０ ~R ２７ Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group; 【Chemistry 4】 In the aforementioned chemical formula 5, Ar ８ and Ar ９ Each of these is independently 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. The Ar １０ and Ar １１ Each of these is 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 ４１ ~R ４５ Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m5 is one of the integers between 1 and 3.

2. Ar in the above chemical formula 1 １ and Ar ２ The organic optoelectronic device according to claim 1, wherein each of them is independently 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 phenantrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

3. L in the aforementioned chemical formula 1 １ -Ar １ and L ２ -Ar ２ Each of these substituents is independently selected from among the substituents listed in Group I below, the organic photoelectronic device according to claim 1: [Group I] 【Transformation 5】 Among the aforementioned group I, R ４６ ~R ４８ Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m6 is one of the integers from 1 to 5. m7 is one of the integers from 1 to 4. m8 is one of the integers from 1 to 3. ＊ represents the bonding site.

4. The first compound is one selected from the compounds listed in Group 1 below, according to claim 1, for the organic photoelectronic device: [Group 1] 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】

5. The organic photoelectronic device according to claim 1, wherein the aforementioned chemical formula 2 is represented by the following chemical formula 2-8. 【Chemistry 12】 In the aforementioned chemical formula 2-8, R ９ ~R １８ Each of these is independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. m1 and m2 are each independently one of the integers from 1 to 3. L ４ -Ar ３ and L ５ -Ar ４ Each of these is independently selected from among the substituents listed in Group II below, [Group II] 【Chemistry 13】 Among the aforementioned group II, R ４９ ~R ５２ Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m9 is one of the integers from 1 to 5. m10 is one of the integers from 1 to 4. m11 is one of the integers from 1 to 3. m12 is an integer of 1 or 2, ＊ represents the bonding site.

6. The combination of chemical formulas 3 and 4 is represented by the following chemical formula 3, which is the organic photoelectronic element according to claim 1: 【Chemistry 14】 In the aforementioned chemical formula 3C, L ａ３ and L ａ４ It is a single bond, R ２０ ~R ２７ , R ｂ３ and R ｂ４ Each of these is independently either hydrogen or an aryl group having 6 to 12 carbon atoms. L ６ -Ar ５ and L ７ -Ar ６ Each of these is independently selected from among the substituents listed in Group II below, [Group II] 【Chemistry 15】 Among the aforementioned group II, R ４９ ~R ５２ Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m9 is one of the integers from 1 to 5. m10 is one of the integers from 1 to 4. m11 is one of the integers from 1 to 3. m12 is an integer of 1 or 2, ＊ represents the bonding site.

7. The aforementioned chemical formula 5 is represented by the following chemical formula 5-4, and is the organic photoelectronic element according to claim 1: 【Chemistry 16】 In the aforementioned chemical formula 5-4, Ar ８ ~Ar １１ , R ４１ ~R ４５ And m5 is as defined in chemical formula 5.

8. The aforementioned chemical formula 5-4 is represented by the following chemical formula 5-4-1, the organic photoelectronic element according to claim 7: 【Chemistry 17】 In the aforementioned chemical formula 5-4-1, Ar ９ ~Ar １１ , R ４１ ~R ４５ And m5 is as defined in claim 1, Ar １２ and Ar １３ Each of these is 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 ５３ ~R ５７ Each of these is independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m13 is one of the integers between 1 and 3.

9. The aforementioned chemical formula 5-4-1 is represented by the following chemical formula 5-4-1b, the organic photoelectronic element according to claim 8: [Chemistry 18] In the aforementioned chemical formula 5-4-1b, Ar ９ ~Ar １３ 、R ４１ ~R ４５ 、R ５３ ~R ５７ 、m5 and m13 are as defined in Chemical Formula 5-4-1.

10. The third compound is one selected from the compounds listed in group 3 below, according to claim 1, for the organic photoelectronic device: [Group 3] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】

11. The aforementioned second compound is represented by the following chemical formula 2-8 or chemical formula 3C, The third compound is represented by the following chemical formula 5-4-1b, and is the organic photoelectronic device according to claim 1: 【Chemistry 23】 In the aforementioned chemical formula 2-8, R ９ ~R １８ Each of these is independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. m1 and m2 are each independently one of the integers from 1 to 3. L ４ -Ar ３ and L ５ -Ar ４ each independently is one selected from the substituents listed in Group II below, [Group II] 【Chemistry 24】 Among the aforementioned group II, R ４９ ~R ５２ Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m9 is one of the integers from 1 to 5. m10 is one of the integers from 1 to 4. m11 is one of the integers from 1 to 3. m12 is an integer of 1 or 2, ＊ is the binding site; 【Chemistry 25】 In the aforementioned chemical formula 3C, L ａ３ and L ａ４ It is a single bond, R ２０ ~R ２７ , R ｂ３ and R ｂ４ Each of these is independently either hydrogen or an aryl group having 6 to 12 carbon atoms. L ６ -Ar ５ and L ７ -Ar ６ Each of these is independently selected from among the substituents listed in Group II below, [Group II] 【Chemistry 26】 Among the aforementioned group II, R ４９ ~R ５２ Each of these is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. m9 is one of the integers from 1 to 5. m10 is one of the integers from 1 to 4. m11 is one of the integers from 1 to 3. m12 is an integer of 1 or 2, ＊ is the binding site; 【Chemistry 27】 In the aforementioned chemical formula 5-4-1b, Ar １０ and Ar １１ Each of these is independently a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. Ar １２ and Ar １３ Each of these is independently a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted C6-C12 aryl group. R ４１ ~R ４５ and R ５３ ~R ５７ Each of these is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. Ar ９ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. m5 and m13 are each independently one of the integers between 1 and 3.

12. A display device comprising an organic photoelectronic element according to any one of claims 1 to 11.

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