Patent Application
20250160200
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0151077 filed in the Korean Intellectual Property Office on Nov. 3, 2023, the entire contents of which are incorporated herein by reference.
Embodiments relate to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device.
An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and optical energy to each other.
Organic optoelectronic devices may be largely divided into two types according to a principle of operation. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes, and transferring the electrons and holes to different electrodes, respectively and the other is light emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.
Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.
Among them, organic light emitting diodes (OLEDs) are attracting much attention in recent years due to increasing demands for flat panel display devices. The organic light emitting diode is a device that converts electrical energy into light, and the performance of the organic light emitting diode is greatly influenced by an organic material between electrodes.
The embodiments may be realized by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:
The embodiments may be realized by providing an organic optoelectronic device, including an anode and a cathode facing each other; and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the compound for an organic optoelectronic device.
The embodiments may be realized by providing a display device including the organic optoelectronic device.
Features will become apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawing in which:
The FIGURE is a cross-sectional view showing an organic light emitting diode according to some embodiments.
Example embodiments will now be described more fully hereinafter with reference to the accompanying drawing; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.
In the drawing FIGURE, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will be understood that when a layer is referred to as being “under” another layer, it can be directly under, and one or more intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout. As used herein, the term “or” is not necessarily an exclusive term, e.g., “A or B” would include A, B, or A and B.
As used herein, when a definition is not otherwise provided, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
In one example, the “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In a specific example, the “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In a specific example, the “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In a specific example, the “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by 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.
“Unsubstituted” refers to non-replacement of a hydrogen atom by another substituent and remaining of the hydrogen atom.
In the present specification, “hydrogen (—H)” may include “deuterium substitution (-D)” or “tritium substitution (-T).” For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).
As used herein, when a definition is not otherwise provided, “hetero” refers to one including one to three heteroatoms selected from N, O, S, P, and Si, and remaining carbons in one functional group.
As used herein, “an aryl group” refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals which form conjugation, for example a phenyl group, a naphthyl group, and the like, two or more hydrocarbon aromatic moieties may be linked by a sigma bond and may be, for example a biphenyl group, a terphenyl group, a quarterphenyl group, and the like, and two or more hydrocarbon aromatic moieties are fused directly or indirectly to provide a non-aromatic fused ring, for example a fluorenyl group.
The aryl group may include a monocyclic, polycyclic, or fused ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional group.
As used herein, “a heterocyclic group” is a generic concept of a heteroaryl group, and may include at least one heteroatom selected from N, O, S, P, and Si instead of carbon (C) in a cyclic compound such as aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. In an implementation, the heterocyclic group may be a fused ring, and the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.
For example, “a heteroaryl group” may refer to aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are linked by a sigma bond directly, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. In an implementation, the heteroaryl group may be a fused ring, and each ring may include one to three heteroatoms.
For example, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof.
For example, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, or a combination thereof.
As used herein, hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.
In addition, electron characteristics refer to an ability to accept an electron when an electric field is applied and that electron formed in the cathode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.
Hereinafter, a compound for an organic optoelectronic device according to some embodiments is described.
The compound for an organic optoelectronic device according to some embodiments may be represented by Chemical Formula 1.
In Chemical Formula 1, X1 may be O or S.
R1 and R2 may each independently be or include, e.g., a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
R3 to R6 may each independently be or include, e.g., hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof.
L1 may be or include, e.g., a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.
Ar1 may be or include, e.g., a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.
m1 may be, e.g., an integer of 1 or 2.
m2 and m3 may each independently be, e.g., an integer of 1 to 3.
m4 may be an integer of 1 to 4.
The compound represented by Chemical Formula 1 may have a structure in which dibenzofuran (or dibenzothiophene) is substituted with two tert-butyl groups and fluorene is substituted with amine, and has fast hole mobility to increase the charge balance, and accordingly, the driving voltage of the organic light emitting diode to which this is applied may be lowered and a longer life-span may be realized.
A compound in which one phenyl ring of the dibenzofuran (or dibenzothiophene) is simultaneously substituted with two tert-butyl groups may be a low refractive index material to increase the efficiency of organic light emitting diodes.
In an implementation, Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-6.
In Chemical Formula 1-1 to Chemical Formula 1-6, X), R1 to R6, L1, Ar), and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-1 may be represented by one of Chemical Formula 1-1A, Chemical Formula 1-1B, Chemical Formula 1-1C, or Chemical Formula 1-1D.
In Chemical Formula 1-1A, Chemical Formula 1-1B, Chemical Formula 1-1C, and Chemical Formula 1-1D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-2 may be represented by one of Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, or Chemical Formula 1-2D.
In Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, and Chemical Formula 1-2D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
Chemical Formula 1-3 may be represented by one of Chemical Formula 1-3A, Chemical Formula 1-3B, Chemical Formula 1-3C, or Chemical Formula 1-3D.
In Chemical Formula 1-3A, Chemical Formula 1-3B, Chemical Formula 1-3C, and Chemical Formula 1-3D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
Chemical Formula 1-4 may be represented by one of Chemical Formula 1-4A, Chemical Formula 1-4B, Chemical Formula 1-4C, or Chemical Formula 1-4D.
In Chemical Formula 1-4A, Chemical Formula 1-4B, Chemical Formula 1-4C, and Chemical Formula 1-4D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
Chemical Formula 1-5 may be represented by one of Chemical Formula 1-5A, Chemical Formula 1-5B, Chemical Formula 1-5C, or Chemical Formula 1-5D.
In Chemical Formula 1-5A, Chemical Formula 1-5B, Chemical Formula 1-5C and Chemical Formula 1-5D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
Chemical Formula 1-6 may be represented by one of Chemical Formula 1-6A, Chemical Formula 1-6B, Chemical Formula 1-6C, or Chemical Formula 1-6D.
In Chemical Formula 1-6A, Chemical Formula 1-6B, Chemical Formula 1-6C, and Chemical Formula 1-6D, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1 may be represented by one of Chemical Formula 1-1A, Chemical Formula 1-2A, Chemical Formula 1-3A, Chemical Formula 1-4A, Chemical Formula 1-5A, or Chemical Formula 1-6A.
In an implementation, Chemical Formula 1-1A may be represented by one of Chemical Formula 1-1A-1 to Chemical Formula 1-1A-4.
In Chemical Formula 1-1A-1 to Chemical Formula 1-1A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-2A may be represented by one of Chemical Formula 1-2A-1 to Chemical Formula 1-2A-4.
In Chemical Formula 1-2A-1 to Chemical Formula 1-2A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-3A may be represented by one of Chemical Formula 1-3A-1 to Chemical Formula 1-3A-4.
In Chemical Formula 1-3A-1 to Chemical Formula 1-3A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-4A may be represented by one of Chemical Formula 1-4A-1 to Chemical Formula 1-4A-4.
In Chemical Formula 1-4A-1 to Chemical Formula 1-4A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-5A may be represented by one of Chemical Formula 1-5A-1 to Chemical Formula 1-5A-4.
In Chemical Formula 1-5A-1 to Chemical Formula 1-5A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-6A may be represented by one of Chemical Formula 1-6A-1 to Chemical Formula 1-6A-4.
In Chemical Formula 1-6A-1 to Chemical Formula 1-6A-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-1B may be represented by one of Chemical Formula 1-1B-1 to Chemical Formula 1-1B-4.
In Chemical Formula 1-1B-1 to Chemical Formula 1-1B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-2B may be represented by one of Chemical Formula 1-2B-1 to Chemical Formula 1-2B-4.
In Chemical Formula 1-2B-1 to Chemical Formula 1-2B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-3B may be represented by one of Chemical Formula 1-3B-1 to Chemical Formula 1-3B-4.
In Chemical Formula 1-3B-1 to Chemical Formula 1-3B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-4B may be represented by one of Chemical Formula 1-4B-1 to Chemical Formula 1-4B-4.
In Chemical Formula 1-4B-1 to Chemical Formula 1-4B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-5B may be represented by one of Chemical Formula 1-5B-1 to Chemical Formula 1-5B-4.
In Chemical Formula 1-5B-1 to Chemical Formula 1-5B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-6B may be represented by one of Chemical Formula 1-6B-1 to Chemical Formula 1-6B-4.
In Chemical Formula 1-6B-1 to Chemical Formula 1-6B-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-1C may be represented by one of Chemical Formula 1-1C-1 to Chemical Formula 1-1C-4.
In Chemical Formula 1-1C-1 to Chemical Formula 1-1C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-2C may be represented by one of Chemical Formula 1-2C-1 to Chemical Formula 1-2C-4.
In Chemical Formula 1-2C-1 to Chemical Formula 1-2C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-3C may be represented by one of Chemical Formula 1-3C-1 to Chemical Formula 1-3C-4.
In Chemical Formula 1-3C-1 to Chemical Formula 1-3C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-4C may be represented by one of Chemical Formula 1-4C-1 to Chemical Formula 1-4C-4.
In Chemical Formula 1-4C-1 to Chemical Formula 1-4C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-5C may be represented by any of Chemical Formula 1-5C-1 to Chemical Formula 1-5C-4.
In Chemical Formula 1-5C-1 to Chemical Formula 1-5C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-6C may be represented by one of Chemical Formula 1-6C-1 to Chemical Formula 1-6C-4.
In Chemical Formula 1-6C-1 to Chemical Formula 1-6C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-1D may be represented by one of Chemical Formula 1-1D-1 to Chemical Formula 1-1D-4.
In Chemical Formula 1-1D-1 to Chemical Formula 1-1D-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-2D may be represented by one of Chemical Formula 1-2D-1 to Chemical Formula 1-2D-4.
In Chemical Formula 1-2D-1 to Chemical Formula 1-2D-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-3D may be represented by one of Chemical Formula 1-3D-1 to Chemical Formula 1-3D-4.
In Chemical Formula 1-3D-1 to Chemical Formula 1-3D-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-4D may be represented by one of Chemical Formula 1-4D-1 to Chemical Formula 1-4D-4.
In Chemical Formula 1-4D-1 to Chemical Formula 1-4D-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-5D may be represented by one of Chemical Formula 1-5D-1 to Chemical Formula 1-5D-4.
In Chemical Formula 1-5D-1 to Chemical Formula 1-5D-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1-6D may be represented by one of Chemical Formula 1-6D-1 to Chemical Formula 1-6D-4.
In Chemical Formula 1-6C-1 to Chemical Formula 1-6C-4, X1, R1 to R6, L1, Ar1, and m1 to m4 may be defined the same as those of Chemical Formula 1.
In an implementation, Chemical Formula 1 may be represented by, e.g., Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, Chemical Formula 1-5A, Chemical Formula 1-5B, or Chemical Formula 1-5C.
In an implementation, Chemical Formula 1 may be represented by, e.g., Chemical Formula 1-2A-2, Chemical Formula 1-2A-3, Chemical Formula 1-2B-2, Chemical Formula 1-2C-2, Chemical Formula 1-5A-2, or Chemical Formula 1-5C-2.
In an implementation, Ar1 may 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl 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, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.
In an implementation, L1 may be or include, e.g., a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
In an implementation, moiety -L1-Ar1 may be, e.g., a moiety of Group I.
In Group I, R9 to R12 may each independently be, e.g., hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.
R13 and R14 may each independently be, e.g., a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.
m5 may be, e.g., an integer of 1 to 5.
m6 may be, e.g., an integer of 1 to 4.
m7 may be, e.g., an integer of 1 to 3.
m8 may be, e.g., an integer of 1 or 2,
* is a linking point.
In an implementation, m5 may be 2, 3, 4, or 5, and each R9 may be the same or different from each other.
In an implementation, m6 may be 2, 3, or 4, and each R10 may be the same or different from each other.
In an implementation, m7 may be 2 or 3, and each R11 may be the same or different from each other.
In an implementation, m8 may be 2, and each R12 may be the same or different from each other.
In an implementation, R1 and R2 may each independently be, e.g., a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.
In an implementation, R3 to R6 may each independently be, e.g., hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C12 aryl group.
In an implementation, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be, e.g., a compound of Group 1.
In the compounds of Group 1, Dn (e.g., D26) means the number of deuterium atoms included, and represents a structure in which hydrogen (protium) substituted with one or more deuterium atoms.
In addition to the aforementioned compounds for organic optoelectronic devices, one or more compounds may be further included. In an implementation, a dopant may be further included. The dopant may be, e.g., a phosphorescent dopant, e.g., a red, green, or blue phosphorescent dopant, e.g., a red or green phosphorescent dopant.
The dopant may be a substance that emits light when mixed in a small amount in a compound or composition for an organic optoelectronic device and in general, may be, a material such as a metal complex that emits light by multiple excitation that excites the triplet state or higher is used. The dopant may be, e.g., an inorganic, organic, or organic/inorganic compound, and may be included in one or two or more types.
In an implementation, the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may use, e.g., a compound represented by Chemical Formula Z.
[Chemical Formula Z]
L2MX2
In Chemical Formula Z, M may be a metal, and L2 and X2 may each independently be ligands forming a complex with M.
M may be, e.g., Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L9 and X may be, e.g., a bidentate ligand.
Examples of the ligands represented by L2 and X2 may include ligands of Group A.
In Group A, R300 to R302 may each independently be, e.g., hydrogen, deuterium a C1 to C30 alkyl group that is substituted or unsubstituted with a halogen, a C6 to C30 aryl group that is substituted or unsubstituted with a C1 to C30 alkyl, or a halogen.
R303 to R324 may each independently be, e.g., hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SFs, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.
n1 may be, e.g., an integer of 1 to 5.
n2 may be, e.g., an integer of 1 to 4.
n3 may be, e.g., an integer 1 to 3.
n4 may be, e.g., an integer of 1 or 2.
n5 may be, e.g., an integer of 1 to 6.
In an implementation, n1 may be 2, 3, 4, or 5, and each substituent may be the same or different from each other.
In an implementation, n2 may be 2, 3, or 4, and each substituent may be the same or different from each other.
In an implementation, n3 may be 2 or 3, and each substituent may be the same or different from each other.
In an implementation, n4 may be 2, and each substituent may be the same or different from each other.
In an implementation, n5 may be 2, 3, 4, 5, 6, and each substituent may be the same or different from each other.
The dopant according to some embodiments may be an iridium complex, and may be represented by, e.g., Chemical Formula 6-1 or Chemical Formula 6-2.
In Chemical Formula 6-1, R101 to R116 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR132R133R134.
R132 to R134 may each independently be a substituted or unsubstituted C1 to C6 alkyl group.
In an implementation, at least one of R101 to R116 may be a functional group represented by Chemical Formula V-1.
L100 may be a bidentate ligand of a monovalent anion, and may be a ligand that coordinates to iridium through a lone pair of carbons or heteroatoms.
m19 and m20 may each independently be an integer of 0 to 3, and m19+m20 may be an integer of 1 to 3.
In Chemical Formula V-1, R135 to R139 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR132R133R134.
* indicates a portion linked to a carbon atom.
In Chemical Formula 6-2, R101 to R117 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR133R134R135.
R133 to R135 may each independently be a substituted or unsubstituted C1 to C6 alkyl group.
L100 may be a bidentate ligand of a monovalent anion, and may be a ligand that coordinates to iridium through a lone pair of carbons or heteroatoms.
n1 and n2 may each independently be an integer of 0 to 3 and n1+n2 may be an integer of 1 to 3.
In an implementation, it may include a dopant represented by Chemical Formula Z-1.
In Chemical Formula Z-1, rings A, B, C, and D may each independently be a 5-membered or 6-membered carbocyclic or heterocyclic ring.
RA, RB, RC, and RD may each independently be mono-, di-, tri-, or tetra-substitution, or unsubstitution.
LB, LC, and LD may each independently be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, and a combination thereof,
In an implementation, nA is 1, LE may be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, and a combination thereof. In an implementaiton, nA is 0, and LE does not exist.
RA, RB, RC, RD, R, and R′ may each independently be hydrogen, deuterium, a halogen, an alkyl group, a cycloalkyl group, a heteroalkyl group, an arylalkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, or a combination thereof. In an implementation, adjacent RA, RB, RC, RD, R, and R′ may be separate or may be linked to each other to provide a ring; XB, XC, XD, and XE may each independently be carbon or nitrogen; and Q1, Q2, Q3, and Q4 may each independently be oxygen or a direct bond.
The platinum complex may be represented, e.g., by Chemical Formula 7-1 or Chemical Formula 7-2.
In Chemical Formula 7-1 and Chemical Formula 7-2, X100 may be O, S, or NR132.
R118 to R132 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR133R134R135
R133 to R135 may each independently be a substituted or unsubstituted C1 to C6 alkyl group.
In an implementation, at least one of R118 to R132 may be —SiR133R134R135 or a tert-butyl group.
R133 to R135 may each independently be a substituted or unsubstituted C1 to C6 alkyl group.
Hereinafter, an organic optoelectronic device to which the aforementioned compound for an organic optoelectronic device may be applied will be described.
The organic optoelectronic device may be any suitable device to convert electrical energy into photoenergy and vice versa, and may be, e.g., an organic photoelectric device, an organic light emitting diode, an organic solar cell, or an organic photo-conductor drum.
Herein, an organic light emitting diode as one example of an organic optoelectronic device is described referring to the drawing.
The
Referring to the FIGURE, an organic light emitting diode 100 according to some embodiments may include an anode 120 and a cathode 110 facing each other and an organic layer 105 between the anode 120 and cathode 110.
The anode 120 may be made of a conductor having a large work function to help hole injection, and may be, e.g., a metal, a metal oxide and/or a conductive polymer. The anode 120 may be, e.g., a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like or an alloy thereof, a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.
The cathode 110 may be made of a conductor having a small work function to help electron injection, and may be, e.g., a metal, a metal oxide, and/or a conductive polymer. The cathode 110 may be, e.g., a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin, lead, cesium, barium, or the like, or an alloy thereof, a multi-layer structure material such as LiF/Al, LiO2/Al, LiF/Ca, or BaF2/Ca.
The organic layer 105 may include the aforementioned compound for an organic optoelectronic device. The organic layer 105 may include the light emitting layer 130, and the light emitting layer 130 may include the aforementioned compound for an organic optoelectronic device.
The light emitting layer 130 may include a composition for an organic optoelectronic device that further includes a dopant. The composition for an organic optoelectronic device may be, e.g., a green light emitting composition.
The light emitting layer 130 may include, e.g., the aforementioned compound for an organic optoelectronic device as a phosphorescent host. The organic layer may further include a charge transport region in addition to the light emitting layer.
The charge transport region may be, e.g., the hole transport region 140. The hole transport region 140 may help further increase hole injection or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
In an implementation, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, wherein the hole transport auxiliary layer may include the aforementioned compound for an organic optoelectronic device. In an implementation, the light emitting layer may include a host and a dopant, and the host may be, e.g., a phosphorescent host.
The phosphorescent host may facilitate the injection and transport of holes and electrons within the emitting layer, ultimately allowing holes and electrons to meet to form excitons, and should be able to transfer the formed exciton energy to the dopant. Examples of phosphorescent host may include an organic compound including, e.g., carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or a combination thereof. The phosphorescent host may be any suitable material. In an implementation, it may be a single host or a mixed host.
In an implementation, the aforementioned compound for an organic optoelectronic device may be included in the light emitting layer, and a compound of Group C may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.
(Dn means the number of deuterium substituted, and represents a structure substituted with one or more deuterium)
In the hole transport region 140, other suitable compounds may be included in addition to the aforementioned compounds.
In an implementation, the charge transport region may be, e.g., the electron transport region 150. The electron transport region 150 may further help increase electron injection or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.
In an implementation, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130, and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer and a compound of Group D may be included in at least one of the electron transport layer and the electron transport auxiliary layer.
Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.
Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.
Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.
The organic light emitting diode according to some embodiments may include a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130 as the organic layer 105, as shown in the FIGURE.
In an implementation, the organic light emitting diode according to some embodiments may further include an electron injection layer, a hole injection layer, or the like, in addition to the light emitting layer as the aforementioned organic layer.
The organic light emitting diode 100 may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film formation method such as a vacuum deposition method (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon. The aforementioned organic light emitting diode may be applied to an organic light emitting display device.
The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples.
Hereinafter, starting materials and reactants used in examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry, or P&H tech as far as there is no particular comment or were synthesized by suitable methods.
10.0 g (31.76 mmol) of an intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan, 13.78 g (38.11 mmol) of an intermediate of N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine, 6.01 g (63.52 mmol) of sodium t-butoxide, and 0.771 g (1.9 mmol) of tri-tert-butylphosphine were dissolved in 317 m1 of toluene, and 0.87 g (0.95 mmol) of Pd2(dba)3 was added thereto and then, stirred under reflux under a nitrogen atmosphere for 12 hours. After a reaction was completed, an organic layer, which was extracted therefrom with ethyl acetate and distilled water, was dried with anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure. A product therefrom was purified through silica gel column chromatography with normal hexane/dichloromethane (in a volume ratio of 3:1), obtaining a target compound, 16.8 g (a yield: 83%) of Compound 1-7 as a white solid.
Calculated value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Analysis value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Compound 1-11 (13.2 g, a yield: 81%) was synthesized in the same manner as in Synthesis Example 1 except that 8.0 g of an intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 11.02 g of an intermediate of N-([1,1′-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Analysis value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Compound 1-22 (16.7 g, a yield: 79%) was synthesized in the same manner as in Synthesis Example 1 except that 9.0 g of an intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 15.9 g of an intermediate of 9,9-dimethyl-N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 89.03; H, 6.93; N, 1.89; O, 2.16
Analysis value: C, 89.03; H, 6.93; N, 1.89; O, 2.16
Compound 1-29 (12.4 g, a yield: 82%) was synthesized in the same manner as in Synthesis Example 1 except that 7.0 g of an intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 10.71 g of an intermediate of bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.32; H, 7.26; N, 2.06; O, 2.35
Analysis value: C, 88.32; H, 7.26; N, 2.06; O, 2.35
Compound 1-37 (16.7 g, a yield: 82%) was synthesized in the same manner as in Synthesis Example 1 except that 10.0 g of an intermediate of 2,4-di-tert-butyl-8-chlorodibenzo[b,d]furan and 13.78 of an intermediate of N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Analysis value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Compound 1-54 (19.9 g, a yield: 78%) was synthesized in the same manner as in Synthesis Example 1 except that 10.0 g of an intermediate of 2,4-di-tert-butyl-8-chlorodibenzo[b,d]furan and 20.04 g of an intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 89.62; H, 6.64; N, 1.74; O, 1.99
Analysis value: C, 89.62; H, 6.64; N, 1.74; O, 1.99
Compound 1-80 (14.5 g, a yield: 81%) was synthesized in the same manner as in Synthesis Example 1 except that 8.0 g of an intermediate of 2,4-di-tert-butyl-7-chlorodibenzo[b,d]furan and 12.98 g of an intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)naphtho[1,2-b]benzofuran-7-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 87.02; H, 6.44; N, 1.99; O, 4.55
Analysis value: C, 87.02; H, 6.44; N, 1.99; O, 4.55
Compound 1-129 (12.3 g, a yield: 76%) was synthesized in the same manner as in Synthesis Example 1 except that 8.0 g of an intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 11.02 g of an intermediate of N-([1,1′-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-3-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Analysis value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Compound 1-205 (18.4 g, a yield: 82%) was synthesized in the same manner as in Synthesis Example 1 except that 10.0 g of an intermediate of 1,3-di-tert-butyl-9-chlorodibenzo[b,d]furan and 15.16 g of an intermediate of N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Analysis value: C, 88.22; H, 7.09; N, 2.19; O, 2.50
Compound 1-223 (17.0 g, a yield: 82%) was synthesized in the same manner as in Synthesis Example 1 except that 10.0 g of an intermediate of 1,3-di-tert-butyl-9-chlorodibenzo[b,d]furan and 14.31 g of an intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 86.34; H, 6.63; N, 2.14; O, 4.89
Analysis value: C, 86.34; H, 6.62; N, 2.14; O, 4.89
Compound 1-269 (14.9 g, a yield: 80%) was synthesized in the same manner as in Synthesis Example 1 except that 8.0 g of an intermediate of 1,3-di-tert-butyl-7-chlorodibenzo[b,d]furan and 13.77 g of an intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)-4-phenyldibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 87.21; H, 6.49; N, 1.92; O, 4.38
Analysis value: C, 87.21; H, 6.49; N, 1.92; O, 4.38
Compound R-1 (27.6 g, a yield: 76%) was synthesized in the same manner as in Synthesis Example 1 except that 15.0 g of an intermediate of 7-(tert-butyl)-1-chlorodibenzo[b,d]furan and 27.93 g of an intermediate of bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 88.57; H, 6.62; N, 2.25; O, 2.56
Analysis value: C, 88.57; H, 6.62; N, 2.25; O, 2.56
Compound R-2 (13.4 g, a yield: 72%) was synthesized in the same manner as in Synthesis Example 1 except that 10.0 g of an intermediate of 1,3-di-tert-butyl-6-(3-chlorophenyl)dibenzo[b,d]furan and 11.4 g of an intermediate of N-([1,1′-biphenyl]-4-yl)-8,10-dihydropyren-4-amine were used in an equivalent ratio of 1:1.2.
Calculated value: C, 89.34; H, 6.53; N, 1.93; O, 2.20
Analysis value: C, 89.34; H, 6.53; N, 1.93; O, 2.20
A glass substrate coated with ITO/Ag/ITO was ultrasonically washed with distilled water. After washing with the distilled water, the glass substrate was ultrasonically washed with acetone or isopropyl alcohol, and dried and then, moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO/Ag/ITO (reflecting electrode) was used as an anode, Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum-deposited on the ITO/Ag/ITO substrate to form a 100 Å-thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1,240 Å to form a hole transport layer. Compound 1-7 obtained in Synthesis Example 1 was deposited on the hole transport layer to a thickness of 320 Å to form a hole transport auxiliary layer. 85 wt % of Host H1 (40%) and Host H2 (60%) were used as a host on the hole transport auxiliary layer, and 15 wt % of PtGD was doped as a dopant to form a 350 Å-thick light emitting layer by vacuum deposition. Subsequently, Compound C was deposited to form a 50 Å-thick electron transport auxiliary layer on the light emitting layer, and Compound D and Liq were simultaneously vacuum-deposited in a ratio of 1:1 to form a 310 Å-thick electron transport layer. On the electron transport layer, Yb and AgMg were sequentially vacuum-deposited, manufacturing an organic light emitting diode.
The structure was ITO/Ag/ITO/Compound A (3% NDP-9 doping, 100 Å)/Compound A (1,240 Å)/hole transport auxiliary layer (320 Å)/light emitting layer [Host (Host H1, Host H2): GD=85 wt %:15 wt %](350 Å)/Compound C (50 Å)/Compound D: Liq (310 Å0/Yb/AgMg.
The diodes of Examples 2 to 11 and Comparative Examples 1 to 2 were manufactured in the same manner as Example 1, except that the compositions of the hole transport auxiliary layer were changed as shown in Table 1.
The obtained organic light emitting diodes were measured regarding a current value flowing in the unit device, while increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by area to provide the results.
Luminance was measured by using a luminance meter (Minolta Cs-1000A), while the voltage of the organic light emitting diodes was increased from 0 V to 10 V.
Using the luminance and current density measured from (1) and (2) above, the luminous efficiency (cd/A) at the same current density (10 mA/cm2) was calculated.
Relative values based on the luminous efficiency of Comparative Example 1 are shown in Table 1.
The results were obtained by maintaining the luminance (cd/m2) at 24,000 cd/m2 and measuring the time for the current efficiency (cd/A) to decrease to 97%.
Relative values based on the life-span measurements of Comparative Example 1 are shown in Table 1.
Referring to Table 1, the efficiency characteristics and life-span characteristics of the organic light emitting diodes to which the compounds according to the Examples were applied were significantly improved compared to the organic light emitting diodes according to the Comparative Examples.
Some embodiments may provide a compound for an organic optoelectronic device that can implement a low-driving, high-efficiency, and long life-span organic optoelectronic device.
Some embodiments may provide an organic optoelectronic device including the compound for an organic optoelectronic device.
Some embodiments may provide a display device including the organic optoelectronic device.
An organic optoelectronic device having high efficiency and a long life-span may be realized.
Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope of the present invention as set forth in the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0151077 | Nov 2023 | KR | national |
