Organic optoelectronic elements and display devices
By structuring the organic optoelectronic element with specific compound compositions and dopants in the light-emitting layers, the device achieves high efficiency, low voltage, and extended lifespan, addressing the limitations of existing OLEDs in flat panel displays.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- SAMSUNG SDI CO LTD
- Filing Date
- 2024-04-24
- Publication Date
- 2026-06-30
Smart Images

Figure 2026521298000001_ABST
Abstract
Description
[Technical Field]
[0001] One embodiment of the present invention relates to an organic optoelectronic element and a display device. [Background technology]
[0002] Organic optoelectronic diodes are devices that can convert electrical energy and light energy into each other.
[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principle. One type is a photoelectric device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transmitted to separate electrodes, generating 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 recently attracted considerable attention due to the increasing demand for flat panel display devices. Organic light-emitting diodes are devices that convert electrical energy into light, and their performance is greatly influenced by the organic material located between the electrodes. [Overview of the Initiative] [Problems that the invention aims to solve]
[0006] One embodiment provides a highly efficient, low-drive-voltage, and long-life organic optoelectronic element. Another embodiment provides a display device including an organic optoelectronic element. [Means for solving the problem]
[0007] According to one embodiment, an organic photoelectronic element is provided that includes a positive electrode and a negative electrode facing each other, and an intermediate layer located between the positive electrode and the negative electrode, the intermediate layer comprising a first light-emitting layer and a second light-emitting layer, the first light-emitting layer located between the positive electrode and the second light-emitting layer and comprising a first host comprising a composition of a first compound and a second compound, and a first dopant, the second light-emitting layer located between the negative electrode and the first light-emitting layer and comprising a second host comprising a composition of a third compound and a fourth compound, the first dopant being an iridium complex and the second dopant being a platinum complex, satisfying the following formula 1.
[0008] [Formula 1] Hole trap index of the first luminescent layer > Hole trap index of the second luminescent layer
[0009] The hole trap index is calculated using the following formula 2. [Formula 2] Hole trap index = [1 - {(Current density measured at 7V after doping the light-emitting layer with a dopant in a HOD (Hole-Only Device)) / (Current density measured at 7V before doping the light-emitting layer with a dopant in a HOD (Hole-Only Device))}] × 100,
[0010] The structure of HOD is ITO / compound E (140 nm) / compound F (10 nm) doped with 1% NDP-9 / compound F (20 nm) / emissive layer (40 nm) / HAT-CN (10 nm) / Ag (5 nm) / Mg:Ag (9:1, 55 nm).
[0011] Compound E is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine.
[0012] Compound F is N-([1,1'-biphenyl]-4-yl)-N-(2-(9,9-diphenyl-9H-fluoren-4-yl)phenyl)-9,9-dimethyll-9H-fluoren-2-amine.
[0013] According to another embodiment, a display device including the aforementioned organic optoelectronic element is provided. [Effects of the Invention]
[0014] This enables the realization of highly efficient, low-drive-voltage, and long-life organic optoelectronic devices. [Brief explanation of the drawing]
[0015] [Figure 1] This is a cross-sectional view showing an organic light-emitting element according to various embodiments. [Figure 2] This is a cross-sectional view showing an organic light-emitting element according to various embodiments. [Figure 3] This is a cross-sectional view showing an organic light-emitting element according to various embodiments. [Figure 4] This is a cross-sectional view showing an organic light-emitting element according to various embodiments. [Figure 5] This is a cross-sectional view showing an organic light-emitting element according to various embodiments. [Modes for carrying out the invention]
[0016] The embodiments of the present invention will be described in detail below.
[0017] However, this is presented as an example only and does not limit the present invention; rather, the present invention is defined solely by the scope of the claims described below.
[0018] In this specification, "substituted" means, unless otherwise defined, that a substituent or at least one hydrogen atom in a 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.
[0019] In one example of the present invention, "substitution" means that at least one hydrogen atom in 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 in 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 in 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 a substituent or at least one hydrogen atom in the 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.
[0020] In this specification, "unsubstituted" means that the hydrogen atom remains as a hydrogen atom and is not substituted by other substituents.
[0021] In this specification, "hydrogen (-H)" may include "deuterium-substituted (-D)" or "tritium-substituted (-T)".
[0022] In this specification, unless otherwise defined, "hetero" means a functional group containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, with the remainder being carbon atoms.
[0023] In this specification, "aryl group" is a general concept encompassing a group having one or more hydrocarbon aromatic moieties, and includes forms in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals are conjugated, such as phenyl groups and naphthyl groups, and forms in which two or more hydrocarbon aromatic moieties are linked by sigma bonds, such as biphenyl groups, terphenyl groups and quarterphenyl groups, and may also include non-aromatic fusion rings in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as fluorenyl groups.
[0024] Aryl groups include monocyclic, polycyclic, or fusion-polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
[0025] In this specification, "heterocyclic group" is a broader concept that includes heteroaryl groups and means a ring compound containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C), such as an aryl group, a cycloalkyl group, a fusion ring thereof, or a combination thereof. If the heterocyclic group is a fusion ring, the heterocyclic group as a whole or each of its rings may contain one or more heteroatoms.
[0026] 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 linked by sigma bonds, or if a heteroaryl group contains two or more rings, the two or more rings can be fused together. If a heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.
[0027] More specifically, the substituted or unsubstituted C6-C30 aryl group 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 phenantrenyl 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 benzophenantrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted ferrylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.
[0028] More specifically, substituted or unsubstituted C2-C30 heterocyclic groups 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, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted indolyl groups, substituted or unsubstituted quinolinyl groups, substituted or Unsubstituted isoquinolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted naphthilidinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzothiadinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted phenazinyl groups, substituted or unsubstituted phenodiadinyl groups, substituted or unsubstituted phenoxazinyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted benzonaphthofuranyl groups, substituted or unsubstituted benzonaphthothiophenyl groups, substituted or unsubstituted benzofuranofurenyl groups, substituted or unsubstituted benzothiophenfluoroenyl groups, or combinations thereof, but are not limited thereto.
[0029] In this specification, hole properties refer to the property of being able to donate electrons and form holes when an electric field is applied, and have conductivity properties according to the HOMO level, and are properties that facilitate 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.
[0030] Furthermore, electronic properties refer to the ability to receive electrons when an electric field is applied, possessing conductivity properties 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.
[0031] In this specification, Dn means the number of deuterium substitutions and can be selected from any integer greater than or equal to 1.
[0032] Organic photoelectronic devices are not particularly limited as long as they are devices that can mutually convert electrical energy and light energy, and examples include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photoreceptor drums.
[0033] Here, we will explain using an organic light-emitting device, which is an example of an organic optoelectronic device, as an example, but the same principles apply to other organic optoelectronic devices without being limited to this example.
[0034] In the drawings, thicknesses are shown enlarged to clearly represent certain layers and regions. Similar parts are given the same reference numerals throughout the specification. When a layer, film, region, plate, or other part 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 one part is said to be "directly on top of" another part, it means that there is no other part in between.
[0035] Figures 1 to 5 are cross-sectional views illustrating various embodiments of organic light-emitting elements. Hereinafter, an embodiment of an organic light-emitting element will be described with reference to Figures 1 to 5.
[0036] Referring to Figure 1, an organic light-emitting element 100 according to one embodiment includes a positive electrode 10 and a negative electrode 20 facing each other, and an intermediate layer 30 located between the positive electrode 10 and the negative electrode 20.
[0037] The positive electrode 10 can be made of a conductor with a high work function to facilitate hole injection, for example, a metal, a metal oxide and / or a conductive polymer. Examples of positive electrodes 10 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 SnO2 and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.
[0038] The negative electrode 20 can be made of a conductor with a low work function to facilitate electron injection, for example, a metal, a metal oxide and / or a conductive polymer. Examples of negative electrodes 20 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 materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca.
[0039] The intermediate layer 30 includes a first light-emitting layer 1 and a second light-emitting layer 1', the first light-emitting layer 1 being located between the positive electrode 10 and the second light-emitting layer 1', and the second light-emitting layer 1' being located between the negative electrode 20 and the first light-emitting layer 1.
[0040] Furthermore, the intermediate layer 30 includes a hole transport region 3 located between the positive electrode 10 and the first light-emitting layer 1, and an electron transport region 4 located between the negative electrode 20 and the second light-emitting layer 1'.
[0041] Referring to Figure 2, the organic light-emitting element 200 according to another embodiment may include an intermediate layer 31 further comprising a charge generation layer 5 between the first light-emitting layer 1 and the second light-emitting layer 1'.
[0042] Referring to Figure 3, the organic light-emitting element 300 according to yet another embodiment may further include an intermediate layer 32 between the negative electrode 20 and the second light-emitting layer 1', which includes a charge generation layer 5 and a third light-emitting layer 1''.
[0043] Referring to Figure 4, an organic light-emitting element 400 according to yet another embodiment includes an intermediate layer 33 comprising a first stack 41 and a second stack 42, wherein the first stack 41 includes a first hole transport region 3 located between the positive electrode 10 and the first light-emitting layer 1, and a first electron transport region 4 located between the negative electrode 20 and the first light-emitting layer 1, and the second stack 42 may include a second hole transport region 3' located between the positive electrode 10 and the second light-emitting layer 1', and a second electron transport region 4' located between the negative electrode 20 and the second light-emitting layer 1'. In this case, a charge generation layer 5 is included between the first stack 41 and the second stack 42.
[0044] As shown in Figures 1 and 3, the first light-emitting layer 1 and the second light-emitting layer 1' can be positioned in contact with each other.
[0045] As shown in Figure 4, in a tandem structure containing two or more stacks, the first light-emitting layer 1 and the second light-emitting layer 1' can be located independently of each other within each stack, and a charge generation layer 5 may be further included between each stack.
[0046] The tandem structure may further include additional stacks, each of which may further include a hole transport region, an electron transport region, an emissive layer, and optionally a charge generation layer between the positive and negative electrodes.
[0047] As an example, referring to Figure 5, the organic light-emitting element 500 includes an intermediate layer 34 comprising a first stack 41, a second stack 42, and a third stack 43. The first stack 41 includes a first hole transport region 3 located between the positive electrode 10 and the first light-emitting layer 1, and a first electron transport region 4 located between the negative electrode 20 and the first light-emitting layer 1. The second stack 42 includes a second hole transport region 3' located between the positive electrode 10 and the second light-emitting layer 1', and a second electron transport region 4' located between the negative electrode 20 and the second light-emitting layer 1'. The third stack 43 may include a third hole transport region 3" located between the positive electrode 10 and the third light-emitting layer 1" and a third electron transport region 4" located between the negative electrode 20 and the third light-emitting layer 1". In this case, charge generation layers 5 and 5' may be included between the first stack 41, the second stack 42, and the third stack 43.
[0048] In an organic photoelectronic device according to one embodiment of the present invention, the first light-emitting layer 1 is located between the positive electrode 10 and the second light-emitting layer 1' and includes a first host containing a composition of the first compound and the second compound, as well as a first dopant; the second light-emitting layer 1' is located between the negative electrode 20 and the first light-emitting layer 1 and includes a second host containing a composition of the third compound and the fourth compound, as well as a second dopant; the first dopant is an iridium complex, and the second dopant is a platinum complex, satisfying the following formula 1. [Formula 1] Hole trap index of the first luminescent layer > Hole trap index of the second luminescent layer
[0049] The hole trap index is calculated using the following formula 2. [Formula 2] Hole trap index = [1 - {(Current density measured at 7V after doping the light-emitting layer with a dopant in a HOD (Hole-Only Device)) / (Current density measured at 7V before doping the light-emitting layer with a dopant in a HOD (Hole-Only Device))}] × 100
[0050] The HOD consists of ITO / compound E (140 nm) / compound F (10 nm) doped with 1% NDP-9 / compound F (20 nm) / emissive layer (40 nm) / HAT-CN (10 nm) / Ag (5 nm) / Mg:Ag (9:1, 55 nm).
[0051] Compound E is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine.
[0052] Compound F is N-([1,1'-biphenyl]-4-yl)-N-(2-(9,9-diphenyl-9H-fluoren-4-yl)phenyl)-9,9-dimethyll-9H-fluoren-2-amine.
[0053] The hole trap index is a numerical representation of the extent to which holes are trapped by a dopant. For example, a hole trap index of 100% means that no holes were trapped by the dopant, while a hole trap index of 0% means that all holes were trapped by the dopant.
[0054] The difference in HOMO energy levels between the dopant and the host allows the dopant to act as a hole trapping site for the host. This results in a difference in hole mobility in the luminescent layer between the host and the dopant contained within the luminescent layer, and this difference is quantified by the hole trapping index.
[0055] When the hole trap index satisfies the above range, the light-emitting zone is positioned relatively towards the positive electrode, resulting in a more advantageous effect on device performance.
[0056] On the other hand, although not limited to a specific concentration, when doping the luminescent layer in HOD with a dopant, the iridium complex (first dopant) can be doped at a concentration of approximately 1-10% by weight, for example, 5-10% by weight, and the platinum complex (second dopant) can be doped at a concentration of approximately 5-15% by weight, for example, 7-12% by weight.
[0057] The difference between the hole trap index of the first light-emitting layer and the hole trap index of the second light-emitting layer may be 30% or more.
[0058] The first compound may be an electron-transporting host and a compound that does not contain carbazole.
[0059] When the first light-emitting layer contains a non-carbazole-based compound with weak hole trap characteristics, the light-emitting zone is relatively arranged on the anode side, so the device performance can be optimized.
[0060] As an example, the first compound can be represented by the following Chemical Formula 1.
[0061]
Chemical Formula
[0062] In Chemical Formula 1, Z 1 ~Z 6 are each independently N or C-L a -R a and Z 1 ~Z 6 at least two of which are N, L a are each independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group, R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, R a each independently exist or adjacent groups are linked to form a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic monocyclic or polycyclic ring.
[0063] As a specific example, chemical formula 1 can be represented by any one of the following: chemical formula 1A, chemical formula 1B, or chemical formula 1C.
[0064] [ka]
[0065] In chemical formulas 1A, 1B, and 1C, Z 1 , Z 3 and Z 5 These are, independently, N or CL a -R a And, Z 1 , Z 3 and Z 5 At least two of them are N, Z 7 ~Z 9 These are, independently, N or CL b -R b And, X 1 is O, S or CR c R d And, L a , L b , and L 1 ~L 3 Each of these is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. Ar 1 and Ar 2 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R a , R b , R c , R d and R 1 ~R 7Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. m1, m2, and m4 are each independently one integer between 1 and 4. m3 and m5 are each independently one of the integers between 1 and 3.
[0066] If m1 is 2 or more, each R 1 They may be the same or different from each other.
[0067] If m2 is 2 or more, each R 2 They may be the same or different from each other.
[0068] If m3 is 2 or more, each R 3 They may be the same or different from each other.
[0069] If m4 is 2 or more, each R 4 They may be the same or different from each other.
[0070] If m5 is 2 or more, each R 5 They may be the same or different from each other.
[0071] As a specific example, chemical formula 1A can be represented by either chemical formula 1A-I or chemical formula 1A-II below. [ka]
[0072] In chemical formulas 1A-I and 1A-II, Z 1 , Z 3 , Z 5 , L 1 ~L 3 Ar1 Ar 2 , R 1 ~R 3 , and m1~m3 are as described above.
[0073] As a specific example, chemical formula 1B is represented by the following chemical formulas 1B-I to 1B-IV. [ka]
[0074] Chemical formula 1B-I~Chemical formula 1B-IV, X 1 , Z 1 , Z 3 , Z 5 , L 1 ~L 3 Ar 1 Ar 2 , R 4 , R 5 m4 and m5 are as described above.
[0075] As a specific example, chemical formula 1C is represented by the following chemical formulas 1C-I to 1C-VI. [ka]
[0076] In chemical formula 1C-I~chemical formula 1C-VI, Z 1 , Z 3 , Z 5 , L 1 ~L 3 Ar 1 Ar 2 , R 6 and R 7 As mentioned above, L b1 ~L b3 These are, independently of the aforementioned L b This is the same as the definition, R b1 ~R b3 These are each independently of the aforementioned R b This is the same as the definition of [the same thing].
[0077] For example, Z 1 and Z 3 are each N, and Z 5 is C-L a -R a may also be.
[0078] For example, Z 1 and Z 5 are each N, and Z 3 is C-L a -R a may also be.
[0079] For example, Z 1 , Z 3 and Z 5 may each be N.
[0080] For example, X 1 may be O or S.
[0081] <Each of these may 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 fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0084] R a , R b and R 1 ~R 7 Each of these may independently be hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.
[0085] R 4 and R 5 These groups may exist independently or adjacent groups may be linked to form a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. The first compound may be, for example, one selected from the compounds listed in Group 1 below.
[0086] [ka]
[0087] [ka]
[0088] [ka]
[0089] [ka]
[0090] [ka]
[0091] [ka]
[0092] [ka]
[0093] [ka]
[0094] [ka]
[0095] The third compound is an electron-transporting host and may be a compound comprising at least one of carbazole and indolocarbazole.
[0096] On the other hand, if the second light-emitting layer contains carbazole, which has excellent hole migration characteristics, as a host, the hole trapping index becomes relatively lower, the light-emitting zone is positioned relatively towards the positive electrode, and the device performance can be optimized.
[0097] The third compound is represented by the following chemical formula 2.
[0098] [ka]
[0099] In chemical formula 2, Z 10 ~Z 12 These are, independently, N or CL c -Re And, Z 10 ~Z 12 At least two of them are N, L c and L 4 ~L 6 Each of these is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof. Ar 3 and Ar 4 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof. R e and R 8 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. m6 is one of the integers from 1 to 4. Ring A can be represented by one of the chemical formulas I-1 to I-4.
[0100] [ka]
[0101] In chemical formula I-1 to chemical formula I-4, R 9 ~R 11 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. R 8 and R 9These groups either exist independently or are linked together to form substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C2-C30 heterocyclic groups. L 7 These are single bonds, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C2-C20 heterocyclic groups, or combinations thereof. Ar 5 These are substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heterocyclic groups, or combinations thereof. m7 and m11 are each independently one of the integers from 1 to 4. m8 is an integer of 1 or 2. * indicates a connection point.
[0102] If m6 is 2 or more, R 8 They may be the same or different from each other.
[0103] If m7 is 2 or greater, R 9 They may be the same or different from each other.
[0104] If m8 is 2 or greater, R 10 They may be the same or different from each other.
[0105] If m9 is 2 or greater, R 11 They may be the same or different from each other.
[0106] Chemical formula 2 can be represented by any one of the following chemical formulas 2A to 2G, depending on the specific structure of the carbazole and carbazole derivatives.
[0107] [ka]
[0108] In chemical formula 2A~chemical formula 2G, Z 10 ~Z 12 , L 4 ~L 7 , R8 ~R 10 Ar 3 ~Ar 5 The definitions of m6 to m8 are as described above.
[0109] Specifically, R in chemical formula 2A 8 and R 9 Each of these may independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0110] For example, R in chemical formula 2A 8 and R 9 Each of these may independently be hydrogen, deuterium, 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.
[0111] For example, R in chemical formulas 2B to 2G 8 , R 10 and R 11 Each of these may independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.
[0112] As a specific example, the third compound may be represented by chemical formula 2A or chemical formula 2B.
[0113] According to one specific embodiment of the present invention, in chemical formula 2A, L 4 ~L 6 Each of these is independently a single bond or a substituted or unsubstituted phenylene group, and Ar 3 and Ar 4Each of these is independently 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, R 8 and R 9 Each of these may independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, but is not limited thereto.
[0114] The third compound may be, for example, one selected from the compounds listed in Group 2 below. [ka]
[0115] [ka]
[0116] [ka]
[0117] [ka]
[0118] [ka]
[0119] [ka]
[0120] [ka]
[0121] [ka]
[0122]
Chem.
[0123]
Chem.
[0124]
Chem.
[0132] In chemical formula 3, Ar 6 and Ar 7 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. L 8 and L 9 Each of these is independently a single bond, or a substituted or unsubstituted C6-C20 arylene group. R 12 ~R 16 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 silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m10, m13, and m14 are each independently one of the integers from 1 to 4. m11 and m12 are each independently one of the integers between 1 and 3. n is one of the integers between 0 and 2.
[0133] [ka]
[0134] In chemical formulas 4 and 5, Ar 8 and Ar 9 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. In chemical formula 4, a1* to a4* are each independently linked carbon (C) or CL. d -R f And, Two adjacent a1* to a4* in chemical formula 4 are linked to the * in chemical formula 5. L d , L 10 and L 11Each of these is independently a single bond, or a substituted or unsubstituted C6-C20 arylene group. R f , R 17 and R 18 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 silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m15 and m16 are each independently one of the integers between 1 and 4.
[0135] In chemical formula 3, if m10 is 2 or more, each R 12 They may be the same or different from each other.
[0136] In chemical formula 2, if m11 is 2 or more, each R 13 They may be the same or different from each other.
[0137] In chemical formula 2, if m12 is 2 or more, each R 14 They may be the same or different from each other.
[0138] In chemical formula 2, if m13 is 2 or more, each R 15 They may be the same or different from each other.
[0139] In chemical formula 2, if m14 is 2 or more, each R 16 They may be the same or different from each other.
[0140] As an example, Ar 6 and Ar 7 Each of these may independently be a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.
[0141] As an example, Ar 6 and Ar 7may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.
[0142] As an example, R in Chemical Formula 3 12 ~R 16 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.
[0143] As a specific example, Ar in Chemical Formula 3 6 and Ar 7 may each independently be a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0144] In Chemical Formulas 4 and 5, when m15 is 2 or more, each R [[ID=2l]] 17 may be the same as or different from each other.
[0145] In Chemical Formulas 4 and 5, when m16 is 2 or more, each R 18 may be the same as or different from each other.
[0146] As an example, Ar in Chemical Formulas 4 and 5 8 and Ar 9 may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.
[0147] As an example, R in Chemical Formulas 4 and 5 f R 17 and R 18Each of these may independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.
[0148] As a specific example, Ar in chemical formulas 4 and 5 8 and Ar 9 Each of these may independently be a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0149] As a more specific example, consider Ar in chemical formula 3. 6 and Ar 7 Each of these 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 anthracenyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted triphenylene 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 of chemical formula 3 8 and L 9 Each of these is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthalenylene group. R in chemical formula 3 12 ~R 16 Each of these is independently hydrogen, deuterium, 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. n may be 0 or 1.
[0150] For example, the "substitution" in chemical formula 3 means that at least one hydrogen atom is substituted with deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group.
[0151] In one specific embodiment of the present invention, chemical formula 3 is represented by one of the following chemical formulas 3-1 to 3-15.
[0152] [ka]
[0153] In chemical formulas 3-1 to 3-15, R 12 ~R 16 Each of these is independently hydrogen, deuterium, 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, *-L 8 -Ar 6 and *-L 9 -Ar 7 Each of these substituents may independently be one of the substituents listed in Group I below.
[0154] [ka]
[0155] In Group I, R 59 ~R 62 These are, independently, hydrogen, deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group. m28 is one of the integers from 1 to 5. m29 is one of the integers from 1 to 4. m30 is one of the integers from 1 to 3. m31 is an integer of 1 or 2. * indicates a connection point.
[0156] In group I, if m28 is 2 or more, each R 59 They may be the same or different from each other.
[0157] In group I, if m29 is 2 or more, each R 60 They may be the same or different from each other.
[0158] In group I, if m30 is 2 or more, each R 61 They may be the same or different from each other.
[0159] In group I, if m31 is 2 or more, each R 62 They may be the same or different from each other.
[0160] In one embodiment, chemical formula 3 is represented by chemical formula 3-8.
[0161] Also, the *-L of chemical formula 3-8. 8 -Ar 6 and *-L 9 -Ar 7 Each of these can be independently selected from Group I, and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.
[0162] As an example, a compound represented by a combination of chemical formulas 4 and 5 can be represented by any one of the following chemical formulas: 4A, 4B, 4C, 4D, and 4E.
[0163] [ka]
[0164] In chemical formulas 4A to 4E, Ar 8 Ar 9 , L 10 , L 11 , R 17 and R 18 As mentioned above, Ld1 ~L d4 As mentioned above, L 10 and L 11 This is the same as the definition, R f1 ~R f4 This is the aforementioned R 17 and R 18 This is the same as the definition of [the same thing].
[0165] For example, Ar of chemical formulas 4 and 5 8 and Ar 9 Each of these is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R f1 ~R f4 , R 17 and R 18 Each of these may independently be hydrogen, deuterium, a cyano 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.
[0166] In a specific embodiment of the present invention, *-L of chemical formulas 4 and 5. 10 -Ar 8 and *-L 11 -Ar 9 Each substituent is independently selected from the substituents listed in Group I.
[0167] In one embodiment, R f1 ~R f4 , R 17 and R 18Each of these may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0168] For example, R f1 ~R f4 , R 17 and R 18 Each of these may independently be hydrogen, deuterium, 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.
[0169] In one specific embodiment, R f1 ~R f4 , R 17 and R 18 Each of these may independently be hydrogen, deuterium, a phenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
[0170] In one specific embodiment of the present invention, the second compound and the fourth compound are each independently represented by chemical formula 3-8, and the Ar of chemical formula 3-8 6 and Ar 7 Each of these 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 anthracenyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted triphenylene 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 8 and L 9 Each of these is independently a single bond, or a substituted or unsubstituted C6-C20 arylene group, and R12 ~R 15 Each of these may independently be hydrogen, deuterium, a cyano 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.
[0171] In another specific embodiment of the present invention, the second and fourth compounds are each independently represented by chemical formula 4C and L of chemical formula 4C. d1 and L d2 It is a single bond, L 10 and L 11 Each of these is independently a single bond, or a substituted or unsubstituted C6-C12 arylene group, and R f1 , R f2 , R 17 and R 18 These are, independently, hydrogen, deuterium, phenyl group, triphenylene group, carbazolyl group, dibenzofuranyl group, or dibenzothiophenyl group, and Ar 8 and Ar 9 Each of these may independently be 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.
[0172] For example, the second and fourth compounds may, but are not limited to, each be independently selected from the compounds listed in Group 3 below.
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[0187] A dopant is a substance that, when mixed in small amounts with a host, induces luminescence. Generally, substances such as metal complexes that emit light through multiple excitation (excitation to a triplet state or higher) are used. Dopant C-88 may be inorganic, organic, or an organic-inorganic compound, and may consist of one or more types.
[0188] Examples of primary dopants include organometallic compounds containing Ir.
[0189] For example, a compound represented by the following chemical formula Z can be used. Chemical formula Z L 12 IrX 2
[0190] In chemical formula Z, L 12 and X 2 These are ligands that are either the same as or different from each other and form complex compounds with Ir.
[0191] L 12 and X 2 This could be, for example, a bidentate ligand. L 12 and X 2 Examples of ligands represented by can be selected from, but are not limited to, the chemical formulas listed in Group A below.
[0192] [ka]
[0193] In Group A, R 300 ~R 302Each of these is independently a hydrogen atom, a deuterium atom, a halogen-substituted or unsubstituted C1-C30 alkyl group, a C1-C30 alkyl-substituted or unsubstituted C6-C30 aryl group, or a halogen. R 303 ~R 324 Each of these is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C1-C30 heteroaryl groups, substituted or unsubstituted C1-C30 amino groups, substituted or unsubstituted C6-C30 arylamino groups, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.
[0194] For example, the first dopant is represented by the following chemical formula V. [ka] chemistry
[0195] In chemical formula V, X 3 is O, S, or Se, CY1 is a substituted or unsubstituted C5-C30 carboncyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group. L 100This is a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group. a1 is one of the integers from 0 to 3. Ar 100 , R 101 , R 102 , R 103 , R 104 and R 105 Each of these independently represents hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C2-C60 alkenyl group, substituted or unsubstituted C2-C60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C1-C10 heterocycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted The C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), k1 is one of the integers from 1 to 8. b1 and b2 are each independently one of the integers from 1 to 4. b3 is one of the integers from 1 to 8. b4 is one of the integers from 1 to 6. m14 is an integer of 1 or 2. m15 is one of the integers from 1 to 3. Q1 to Q9 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C2-C60 alkenyl group, substituted or unsubstituted C2-C60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C1-C10 heterocycloalkyl group The group is a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.
[0196] On the other hand, an example of a second dopant is an organometallic compound containing Pt. For example, the dopant represented by the following chemical formula Z-1 can be cited.
[0197] [ka]
[0198] In chemical formula Z-1, Rings A, B, C, and D each independently represent a 5-membered or 6-membered carbon ring or heteroring. R A , R B , R C , and R D Each of these independently represents a mono-substitution, di-substitution, tri-substitution, or tetra-substitution, or a non-substitution. L B , L C , and L D Each of these is independently selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof. If nA is 1, L E The group is selected from the direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof, and if nA is 0, L E It does not exist. R A , R B , R C , R D R, and R' are, respectively, hydrogen, deuterium, halogen, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 heteroalkyl group, substituted or unsubstituted C6-C60 arylalkyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C6-C60 aryloxy group, amino group, silyl group, substituted or unsubstituted C2-C60 alkenyl group, substituted or unsubstituted Alternatively, any adjacent R is independently selected from the group consisting of unsubstituted C3-C10 cycloalkenyl groups, substituted or unsubstituted C1-C10 heteroalkenyl groups, substituted or unsubstituted C2-C60 alkynyl groups, substituted or unsubstituted C6-C60 aryl groups, C1-C60 heteroaryl groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, and any adjacent R A , R B , R C , R D R, and R' can be optionally connected to form a ring, X B , X C , XD , and X E Each is independently selected from the group consisting of carbon and nitrogen, Q 1 Q 2 Q 3 , and Q 4 These represent oxygen or a direct bond, respectively.
[0199] The second dopant according to one embodiment is represented by the following chemical formula VI. [ka]
[0200] In chemical formula VI, X 100 O, S and NR 131 Selected from, R 117 ~R 131 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, R 132 ~R 134 Each of these is independently a substituted or unsubstituted C1-C6 alkyl group. R 117 ~R 131 At least one of them is -SiR 132 R 133 R 134 , or tert-butyl group, R 132 ~R 134 Each of these is independently a substituted or unsubstituted C1-C6 alkyl group.
[0201] By positioning an Ir complex with relatively strong hole-trapping properties near the hole transport region, and a Pt complex with weak hole-trapping properties near the electron transport region, the position of the luminescence zone can be appropriately adjusted.
[0202] In one embodiment, the first light-emitting layer and the second light-emitting layer can be positioned in contact with each other.
[0203] In another embodiment, at least one of a hole transport region, an electron transport region, and a charge generation layer (CGL) may be further included between the first light-emitting layer and the second light-emitting layer.
[0204] The hole transport regions 3, 3', and 3'' can further enhance hole injection and / or hole mobility between the positive electrode 10 and the light-emitting layers 1, 1', and 1'', thereby blocking electrons.
[0205] Specifically, the hole transport regions 3, 3', and 3'' may include a hole transport layer between the positive electrode 10 and the light-emitting layers 1, 1', and 1'', and a hole transport auxiliary layer between the light-emitting layers 1, 1', and 1'' and the hole transport layer.
[0206] At least one of the compounds listed in Group B below may be included in at least one of the hole transport layer and hole transport auxiliary layer.
[0207] [ka]
[0208] [ka]
[0209] [ka]
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[0213] In addition to the compounds mentioned above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and compounds with similar structures can also be used in the hole transport regions 3, 3', and 3''.
[0214] The electron transport regions 4, 4', and 4'' can further enhance electron injection and / or electron mobility between the negative electrode 20 and the light-emitting layers 1, 1', and 1'' to block holes.
[0215] Specifically, the electron transport regions 4, 4', and 4'' may include an electron transport layer between the negative electrode 20 and the light-emitting layers 1, 1', and 1'', and an electron transport auxiliary layer between the light-emitting layers 1, 1', and 1'' and the electron transport layer, and at least one of the compounds listed in group C below is included in at least one of the electron transport layer and the electron transport auxiliary layer.
[0216] [ka]
[0217] [ka]
[0218] [ka]
[0219] On the other hand, the organic light-emitting device may also include an electron injection layer (not shown) in addition to the aforementioned intermediate layer.
[0220] Furthermore, a capping layer (not shown) may be further included on the positive and / or negative electrodes.
[0221] The capping layer is included to enhance thermal stability, increase environmental stability, and improve the performance of the organic light-emitting element. Examples of capping layers that can be used to improve the thermal stability of the organic light-emitting element include, but are not limited to, SiO, SiO2, amine compounds, or mixtures thereof.
[0222] Organic light-emitting diodes can be manufactured by first forming a positive or negative electrode on a substrate, then forming an intermediate 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 intermediate layer.
[0223] The organic light-emitting element described above can be applied to an organic light-emitting display device. [Examples]
[0224] 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.
[0225] Unless otherwise specified, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, or P&Htech, or synthesized by known methods.
[0226] (Synthesis of the first compound) Synthesis Example 1: Synthesis of Compound A-3
[0227] [ka]
[0228] Compound A-3 was synthesized by referring to the method publicly known in KR10-1649683B1.
[0229] Synthesis Example 2: Synthesis of Compound D-130
[0230] [ka]
[0231] Compound D-130 was synthesized by referring to the method publicly known in KR10-2193015B1.
[0232] Synthesis Example 3: Synthesis of Compound D-12
[0233] [ka]
[0234] Compound D-12 was synthesized by referring to the method publicly known in KR10-2430047B1.
[0235] Synthesis Example 4: Synthesis of Compound B-136
[0236] [ka]
[0237] Compound B-136 was synthesized by referring to the method publicly known in KR10-1649683B1.
[0238] Synthesis Example 5: Synthesis of Compound B-40
[0239] [ka]
[0240] Compound B-40 was synthesized by referring to the method publicly known in KR10-2023-0007931A.
[0241] Synthesis Example 6: Synthesis of Compound B-139
[0242] [ka]
[0243] Compound B-139 was synthesized by referring to the method publicly known in KR10-2023-0007931A.
[0244] Synthesis Example 7: Synthesis of IrGD
[0245] [ka]
[0246] IrGD was synthesized by referring to the method publicly known in KR10-2022-0125767A.
[0247] Synthesis Example 8: Synthesis of PtGD
[0248] [ka]
[0249] PtGD was synthesized by referring to the method publicly known in KR10-2022-0136951A.
[0250] Example 1 A glass substrate coated with a thin film of ITO (Indium tin oxide) was cleaned using distilled water ultrasonic cleaning. After the distilled water cleaning, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, the substrate was transferred to a plasma cleaning machine. After cleaning the substrate using oxygen plasma for 10 minutes, the substrate was transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as the positive electrode, a 10 nm thick hole injection layer was formed by vacuum deposition of compound A doped with 3% NDP-9 (commercially available from Novaled) onto the top of the ITO substrate. A hole transport layer was formed by depositing compound A to a thickness of 135 nm on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound B to a thickness of 35 nm on top of the hole transport auxiliary layer. A first light-emitting layer (EML1) was formed on top of the hole transport auxiliary layer, followed by a second light-emitting layer (EML2). The configurations of the first and second light-emitting layers are described separately in the Examples and Comparative Examples below. Next, compound C was deposited to a thickness of 5 nm 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 30 nm. Yb was deposited to a thickness of 15 Å on top of the electron transport layer to form an electron injection layer, Mg and Ag were simultaneously vacuum-deposited in a 1:9 weight ratio to a thickness of 1.5 nm to form a negative electrode, and compound E was deposited to a thickness of 30 nm on top of the negative electrode to form a capping layer.
[0251] The device structure consisted of compound A (10 nm) doped with ITO / 3%NDP-9, compound A (135 nm), compound B (35 nm), EML1, EML2, compound C (5 nm), compound D:LiQ (30 nm), Yb (1.5 nm), Mg:Ag (15 nm), and compound E (30 nm).
[0252] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine
[0253] Compound B: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine
[0254] Compound C: 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine
[0255] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)
[0256] Compound E: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine
[0257] [ka]
[0258] Examples 2-6 and Comparative Examples 1-6 An organic light-emitting element was fabricated in the same manner as in Example 1, except that the composition was changed as shown in Tables 1 and 2 below.
[0259] Method for manufacturing a Hole-Only Element (HOD) ITO / Compound E (140nm) / Compound F (10nm) doped with 1% NDP-9d / Compound F (20nm) / EML (host, 40nm) / HAT-CN (10nm) / Ag (5nm) / Mg:Ag (9:155nm)
[0260] Compound F:N-([1,1'-biphenyl]-4-yl)-N-(2-(9,9-diphenyl-9H-fluoren-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine
[0261] Hole Trap Index The hole trapping index due to the dopant in the light-emitting layer can be expressed by the following equation 2.
[0262] The rate of decrease in the current density of the HOD before and after doping the light-emitting layer with a dopant can be considered to represent the degree to which holes are trapped by the dopant, i.e., the hole trapping index. A hole trapping index of 100% means that no holes were trapped by the dopant, and a hole trapping index of 0% means that none of the holes were trapped.
[0263] [Formula 2] Hole trap index = [1 - {current density measured at 7V after doping the light-emitting layer with a dopant in HOD / current density measured at 7V before doping the light-emitting layer with a dopant in HOD}] × 100
[0264] The HOD is as described above, and the hole trap index is as shown in Table 1.
[0265] evaluation The compositions of the organic light-emitting devices in Examples 1-6 and Comparative Examples 1-6 are as shown in Table 2, and their luminous efficiency and lifetime characteristics were evaluated.
[0266] The specific measurement methods are as follows, and the results are shown in Tables 3 and 4.
[0267] (1) Measurement of change in current density due to voltage change For the fabricated 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.
[0268] (2) Measurement of brightness change due to voltage change The luminance of the fabricated 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.
[0269] (3) Measurement of luminous efficiency Using the brightness, current density, and voltage measured from (1) and (2), the same current density (10 mA / cm²) is used. 2 The current efficiency (cd / A) was calculated.
[0270] The luminous efficiency values for Examples 1-3 and Comparative Examples 1-3 were calculated as relative values based on Example 1 and are shown in Table 3 below.
[0271] (4) Lifespan measurement Brightness of 24,000 cd / m² 2 The results were obtained by maintaining the current level and measuring the time it took for the current efficiency (unit: cd / A) to decrease to 97%.
[0272] The life measurements for Examples 4-6 and Comparative Examples 4-6 were calculated as relative values based on Example 6 and are shown in Table 4 below.
[0273] [Table 1]
[0274] [Table 2]
[0275] [Table 3]
[0276] Referring to Table 3, it can be confirmed that the organic light-emitting devices of Examples 1 to 3 showed a significant improvement in luminous efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 3. Comparing Example 3 with Comparative Example 3, in Example 3, the hole trapping index due to the dopant of the first light-emitting layer was 76%, and the hole trapping index due to the dopant of the second light-emitting layer was 45%. By including a compound with strong hole-trapping properties in the first light-emitting layer, the light-emitting zone is formed to be relatively adjacent to the positive electrode, thereby exhibiting an efficiency improvement effect. Furthermore, Examples 1 to 3 showed that increasing the doping concentration in the first light-emitting layer optimized the hole-electron balance, resulting in improved luminous efficiency.
[0277] In contrast, in Comparative Example 1, the hole trapping index by the dopant in the first light-emitting layer was 45%, and the hole trapping index by the dopant in the second light-emitting layer was 76%. Because the light-emitting zone was formed relatively adjacent to the negative electrode, the light-emitting zone was not formed in the appropriate position, and in Comparative Examples 1 to 3, increasing the doping concentration of the second light-emitting layer actually resulted in a decrease in efficiency.
[0278] [Table 4]
[0279] Referring to Table 4, it can be confirmed that the organic light-emitting devices of Examples 4 to 6 have significantly improved lifetimes compared to the organic light-emitting devices of Comparative Examples 4 to 6. From Example 6 to Example 4, as the thickness of the first light-emitting layer decreases, the position of the light-emitting zone moves relatively towards the positive electrode, resulting in improved lifetimes. In the case of Comparative Example 4, the first light-emitting layer contains a carbazole compound with excellent hole transport capability, resulting in a weak hole trap index of 30% by the dopant. On the other hand, in Comparative Example 4, the hole trap index by the dopant of the second light-emitting layer is 45%, so the light-emitting zone is relatively located in the center, resulting in a decrease in lifetime characteristics. Furthermore, because the second light-emitting layer contains a compound with a weak hole trap index, no effect of improving lifetimes appeared even when the thickness changed. [Explanation of symbols]
[0280] 100, 200, 300, 400... Organic light-emitting elements 10...Positive electrode 20...Negative electrode 30, 31, 32, 33, 34... Middle class 41...First stack 42...Second stack 43 Third Stack 1, 1', 1"...Emitting layer 3, 3', 3''... Hole transport region 4, 4', 4”...electron transport region
Claims
1. The positive and negative poles facing each other, It includes an intermediate layer located between the positive electrode and the negative electrode, The intermediate layer includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer is located between the positive electrode and the second light-emitting layer and comprises a first host containing a composition of the first compound and the second compound, and a first dopant. The second light-emitting layer is located between the negative electrode and the first light-emitting layer and comprises a second host containing compositions of the third and fourth compounds, and a second dopant. The first dopant is an iridium complex, and the second dopant is a platinum complex. The following equation 1 is satisfied, [Formula 1] Hole trap index of the first luminescent layer > Hole trap index of the second luminescent layer The aforementioned hole trap index is calculated by the following formula 2. [Formula 2] Hole trap index = [1 - {(current density measured at 7V after doping the light-emitting layer with a dopant in a hole-only device) / (current density measured at 7V before doping the light-emitting layer with a dopant in a hole-only device)}] × 100 The structure of the aforementioned hole-only element is, The structure is ITO / compound E (140 nm) / compound F (10 nm) doped with 1% NDP-9 / compound F (20 nm) / emissive layer (40 nm) / HAT-CN (10 nm) / Ag (5 nm) / Mg:Ag (9:1, 55 nm), The compound E is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-ffluoren-2-amine, The compound F is N-([1,1'-biphenyl]-4-yl)-N-(2-[9,9-diphenyl-9H-fluoren-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, which is an organic optoelectronic device.
2. The organic optoelectronic element according to claim 1, wherein the difference between the hole trap index of the first light-emitting layer and the hole trap index of the second light-emitting layer is 30% or more.
3. The first compound is an electron-transporting host and does not contain carbazole, according to claim 1.
4. The first compound is represented by the following chemical formula 1, 【Chemistry 1】 In the aforementioned chemical formula 1, Z 1 ~Z 6 These are, independently, N or C-L a -R a And, Z 1 ~Z 6 At least two of them are N, L a Each of these is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. R a These are, independently, hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R a is, independently of each other, present or adjacent groups are linked to form a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic monocyclic or polycyclic ring, the organic optoelectronic device according to claim 3.
5. The aforementioned chemical formula 1 is represented by one of the following chemical formulas 1A, 1B, and 1C: 【Chemistry 2】 In the aforementioned chemical formulas 1A, 1B, and 1C, Z 1 Z 3 and Z 5 These are, independently, N or C-L a -R a And, Z 1 Z 3 and Z 5 At least two of them are N, Z 7 ~Z 9 These are, independently, N or C-L b -R b And, X 1 is O, S or CR c R d And, L a , L b , and L 1 ~L 3 Each of these is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. Ar 1 and Ar 2 These are, independently, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R a , R b , R c , R d and R 1 ~R 7 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. R 4 and R 5 These groups may exist independently, or adjacent groups may be linked to form substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C2-C30 heterocyclic groups. m1, m2, and m4 are each independently one of the integers from 1 to 4. m3 and m5 are each independently one of the integers from 1 to 3, as described in claim 4.
6. The organic optoelectronic device according to claim 1, wherein the third compound is an electron-transporting host and comprises at least one of carbazole and indrocarbazole.
7. The third compound described above is represented by the following chemical formula 2, 【Transformation 3】 In the aforementioned chemical formula 2, Z 10 ~Z 12 These are, independently, N or C-L c -R e And, Z 10 ~Z 12 At least two of them are N, L c and L 4 ~L 6 Each of these is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof. Ar 3 and Ar 4 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof. R e and R 8 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. m6 is one of the integers from 1 to 4. Ring A is represented by one of the chemical formulas I-1 to I-4. 【Chemistry 4】 In the aforementioned chemical formulas I-1 to I-4, R 9 ~R 11 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof. R 8 and R 9 These groups may exist independently, or adjacent groups may be linked to form substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C2-C30 heterocyclic groups. L 7 These are single bonds, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C2-C20 heterocyclic groups, or combinations thereof. Ar 5 These are substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heterocyclic groups, or combinations thereof. m7 and m9 are each independently one of the integers from 1 to 4. m8 is an integer of 1 or 2, * indicates a connection point, as described in claim 6.
8. The aforementioned chemical formula 2 is represented by any one of the following chemical formulas 2A, 2B, 2C, 2D, 2E, 2F, and 2G: 【Transformation 5】 【Transformation 6】 In the chemical formulas 2A to 2G, Z 10 ~Z 12 , L 4 ~L 6 Ar 3 Ar 4 , R 8 ~R 11 The organic optoelectronic element according to claim 7, wherein the definitions of m6 to m9 are as defined in claim 7.
9. The organic optoelectronic device according to claim 1, wherein the second compound and the fourth compound are hole-transporting hosts, are the same or different, and each independently comprises at least one of carbazole and indrocarbazole.
10. The second and fourth compounds are each independently represented by the following combination of chemical formula 3 or chemical formula 4 and chemical formula 5: 【Transformation 7】 In the aforementioned chemical formula 3, Ar 6 and Ar 7 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. L 8 and L 9 Each of these is independently a single bond, or a substituted or unsubstituted C6-C20 arylene group. R 12 ~R 16 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 silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. m10, m13, and m14 are each independently one of the integers from 1 to 4. m11 and m12 are each independently one of the integers from 1 to 3. n is one integer between 0 and 2. 【Transformation 8】 In the aforementioned chemical formulas 4 and 5, Ar 8 and Ar 9 Each of these is independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. Chemical formula 4a 1 *~ a 4 *Each of these independently represents linked carbon (C) or C-L d -R f And, Chemical formula 4a 1 *~ a 4 Two adjacent *s are linked to the * in chemical formula 5. L d , L 10 and L 11 Each of these is independently a single bond, or a substituted or unsubstituted C6-C20 arylene group. R f , R 17 and R 18 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 silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group. The organic optoelectronic element according to claim 9, wherein m15 and m16 are each independently one of the integers from 1 to 4.
11. The aforementioned chemical formula 3 is represented by one of the following chemical formulas 3-1 to 3-15: 【Chemistry 9】 【Chemistry 10】 Among the chemical formulas 3-1 to 3-15, R 12 ~R 16 Each of these is independently hydrogen, deuterium, 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. *-L 8 -Ar 6 and *-L 9 -Ar 5 is each independently one of the substituents listed in the following Group I, 【Chemistry 11】 Among the aforementioned group I, R 59 ~R 62 Each of these is independently hydrogen, deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group. m28 is one of the integers from 1 to 5. m29 is one of the integers from 1 to 4. m30 is one of the integers from 1 to 3. m31 is an integer of 1 or 2. * indicates a connection point, as described in claim 10.
12. The combination of chemical formula 4 and chemical formula 5 is represented by one of the following chemical formulas 4A to 4E: 【Chemistry 12】 In the chemical formulas 4A to 4E, R 17 and R 18 Each of these is independently hydrogen, deuterium, 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. * - L 10 - Ar 8 and * - L 11 - Ar 9 is each independently one of the substituents listed in the following Group I, 【Chemistry 13】 Among the aforementioned group I, R 59 ~R 62 Each of these is independently hydrogen, deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group. m28 is one of the integers from 1 to 5. m29 is one of the integers from 1 to 4. m30 is one of the integers from 1 to 3. m31 is an integer of 1 or 2. * indicates a connection point, as described in claim 10.
13. The iridium complex is represented by the following chemical formula V: 【Chemistry 14】 In the aforementioned chemical formula V, X 3 is O, S, or Se, CY 1 These are substituted or unsubstituted C5-C30 carboncyclic groups, or substituted or unsubstituted C1-C30 heterocyclic groups. L 100 This is a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group. a1 is one of the integers from 0 to 3. Ar 100 , R 101 , R 102 , R 103 , R 104 and R 105 Each of these independently represents hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C60 alkyl groups, substituted or unsubstituted C2-C60 alkenyl groups, substituted or unsubstituted C2-C60 alkynyl groups, substituted or unsubstituted C1-C60 alkoxy groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C1-C10 heterocycloalkyl groups, substituted or unsubstituted C3-C10 cycloalkenyl groups, substituted or unsubstituted The C2-C10 heterocycloalkenyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or substituted C6-C60 arylthio group, substituted or unsubstituted C1-C60 heteroaryl group, substituted or unsubstituted C1-C60 heteroaryloxy group, substituted or unsubstituted C1-C60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), k1 is one of the integers from 1 to 8. b1 and b2 are each independently one of the integers from 1 to 4. b3 is one of the integers from 1 to 8. b4 is one of the integers from 1 to 6. m14 is an integer of 1 or 2. m15 is one of the integers from 1 to 3. Each of the above Q1 to Q9 is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C2-C60 alkenyl group, substituted or unsubstituted C2-C60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C1-C10 heterocycloalkyl group, substituted or The organic optoelectronic device according to claim 1, wherein is an unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.
14. The aforementioned platinum complex is represented by the following chemical formula VI, 【Chemistry 15】 In the aforementioned chemical formula VI, X 100 O, S and NR 131 Selected from, R 117 ~R 131 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 134 Each of these is independently a substituted or unsubstituted C1-C6 alkyl group. R 117 ~R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl group, R 132 ~R 134 The organic photoelectronic element according to claim 1, wherein each of them is independently a substituted or unsubstituted C1-C6 alkyl group.
15. The organic photoelectronic element according to claim 1, wherein the first light-emitting layer and the second light-emitting layer are in contact with each other.
16. The organic optoelectronic device according to claim 1, further comprising at least one of a hole transport region, an electron transport region, and a charge generation layer between the first light-emitting layer and the second light-emitting layer.
17. A display device comprising an organic photoelectron element according to any one of claims 1 to 16.