CN108463535B - Organic light emitting element - Google Patents
Organic light emitting element Download PDFInfo
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- CN108463535B CN108463535B CN201780002448.9A CN201780002448A CN108463535B CN 108463535 B CN108463535 B CN 108463535B CN 201780002448 A CN201780002448 A CN 201780002448A CN 108463535 B CN108463535 B CN 108463535B
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- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000000126 substance Substances 0.000 claims description 74
- -1 cyano, nitro, amino Chemical group 0.000 claims description 69
- 239000000463 material Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000002019 doping agent Substances 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- DXJPAROGPFPUHR-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)c1ccccc1-c1ccccc1.OB(O)c1ccccc1-c1ccccc1 DXJPAROGPFPUHR-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
The present invention relates to an organic light-emitting element free from distortion of a light emission spectrum.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2016-.
The invention relates to the distortion of the luminescence spectrum
The organic light-emitting device of (1).
Background
In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research has been conducted.
An organic light emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting element, the organic layer is often formed of a multilayer structure, and the multilayer structure is formed of different materials, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.
As for organic materials used for the organic light emitting element as described above, development of new materials is continuously demanded.
In addition, the light-emitting layer of the organic light-emitting element is composed of one or more host substances and a light-emitting dopant substance that actually emits light. Therefore, each substance of the light-emitting dopant exhibits an inherent light emission spectrum, but depending on the kind or combination of the host substance used, shift (spectral shift) of the light emission spectrum often occurs, and a desired color cannot be obtained. As a result, in the organic light emitting element using a color filter (color filter), the light transmission range of the color filter is not satisfied, and thus the problem of the final efficiency decrease occurs. In addition, in an organic light-emitting element not using a color filter, a color different from the color of the light-emitting dopant actually required is generated, and a problem arises in color and luminance expression.
Therefore, as described later, the present inventors have identified an organic light emitting element capable of solving the above-described problems, and have confirmed the present invention.
Documents of the prior art
Patent document
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
The present invention aims to provide an organic light-emitting element free from distortion of an emission spectrum.
In order to solve the above problem, the present invention provides an organic light emitting device, including: an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer contains a compound having a dipole moment (dipole moment) value of 4.5 or less as a first host material.
The organic light-emitting element according to the present invention can provide an organic light-emitting element free from distortion of an emission spectrum by using a host material and a dopant that satisfy a specific dipole moment value.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, and a cathode 4.
Fig. 3 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, an electron injection layer 8, and a cathode 4.
Fig. 4 shows the luminescence spectra of the examples of the present invention and the comparative examples.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
Definition of terms
In the context of the present specification,
and
represents a bond to another substituent.
The term "substituted or unsubstituted" as used herein means a compound selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group(s) ((R))
Alkyl thio), arylthio(s) ((R)
Aryl thio), alkyl sulfoxide group(s) ((s)
Alkyl sulfonyl), aryl sulfoxide group(s) ((s)
Aryl sufoxy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, or a heterocyclic group containing at least one of N, O and S atoms, or a substituent formed by connecting at least 2 of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
The number of carbon atoms of the carbonyl group in the present specification is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the ester group, the oxygen atom of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be represented by the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine, or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadiene, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Azolyl group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
Luminescent layer
The present invention provides an organic light emitting element, including: an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer contains a compound having a dipole moment (dipole moment) value of 4.5 or less as a host material.
Depending on the type or combination of host materials included in a light-emitting layer of an organic light-emitting element, shift (spectrum shift) of the emission spectrum of a dopant may occur. This is caused by a solid state solvation effect (solid state solvation effect) due to dipole moment of the host material, and a desired emission spectrum cannot be obtained, which causes problems such as a defect and a decrease in efficiency.
Thus, the present invention is characterized in that a compound having a dipole moment (dipole moment) value of 4.5 or less is used as a host material of a light-emitting layer so as to minimize shift (spread shift) of an emission spectrum of the light-emitting layer of the organic light-emitting element.
The term "dipole moment (dipole moment)" used in the present specification is a physical quantity indicating the magnitude of the polarity, and can be calculated by the following equation 3.
[ mathematical formula 3]
·ρ(r0): molecular Density (molecular Density)
V: volume (volume)
R: observation point (the point of observation)
·d3r0Per unit of unitVolume (an elementary volume)
In the above equation 3, the value of the dipole moment can be obtained by calculating the Molecular density (Molecular density). For example, the molecular density can be obtained by obtaining each atomic Charge (Charge) and Dipole (Dipole) by using a herschifeld Charge Analysis (Hirshfeld Charge Analysis) method, calculating the molecular density from the following equation, and obtaining the Dipole Moment (Dipole Moment) by substituting the calculation result into the above equation 3.
·ρα(r-Rα): spherical mean ground state density
(spherically averaged ground-state amomic density)
·
: density of quasi-molecule
(promolecule density)
ρ (r): molecular Density (molecular Density)
·ρα(r-Rα): at the coordinate RαDensity of free atoms alpha of
(density of the free atomαlocated at coordinates Rα)
q(α)＝-∫ρd(r)Wα(r)d3r
·Wα(r): weight function (weight function)
As described above, in the case of using a compound having a dipole moment (dipole moment) value of 4.5 or less as a host material of the light-emitting layer, a solid state solvation effect hardly occurs, and thus the shift (spread shift) of the emission spectrum can be minimized.
Preferably, the light-emitting layer contains a light-emitting dopant, and the host material and the light-emitting dopant satisfy the following formula 1:
[ mathematical formula 1]
[ fh × DM (host material) + fd × DM (luminescent dopant) ] < 4.5
In the above-mentioned mathematical formula 1,
DM (host material) and DM (light emitting dopant) are dipole moment values of the host material and the light emitting dopant, respectively,
fh represents a value obtained by dividing the weight of the host material by the total weight of the host material and the light-emitting dopant,
fd represents a value obtained by dividing the weight of the light-emitting dopant by the total weight of the host material and the light-emitting dopant.
In addition, it is preferable that the light emitting layer contains n kinds of substances different from each other, where n is an integer of 2 or more, at least one of the n kinds of substances is a light emitting dopant, and the n kinds of substances satisfy the following formula 2:
[ mathematical formula 2]
In the above-mentioned mathematical formula 2,
DMirepresenting the values of the dipole moments of the respective substances,
Aithe weight of each substance is divided by the total weight of the n substances.
Preferably, n is 2,3 or 4.
That is, the light-emitting layer of the organic light-emitting element according to the present invention may contain a compound having a dipole moment value of more than 4.5 in addition to a compound having a dipole moment value of 4.5 or less, but depending on the concentration thereof, the dipole moment value as a whole must be 4.5 or less.
As the host material, a compound having a dipole moment (dipole moment) value of 4.5 or less can be used, and as an example, a compound represented by the following chemical formula 1 or a compound represented by the following chemical formula 2 can be used:
[ chemical formula 1]
In the chemical formula 1 described above,
Ar11and Ar12Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing at least one heteroatom selected from N, O and S2-60(ii) a heteroaryl group, wherein,
L11and L12Each independently is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
R1each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl radical, C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group,
h and i are each independently 1 or 2,
x is an integer of 0 to 8,
[ chemical formula 2]
In the chemical formula 2 described above, the,
Ar21、Ar22and Ar23Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing at least one heteroatom selected from N, O and S2-60(ii) a heteroaryl group, wherein,
L21、L22and L23Each independently is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
R2each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group,
m, n and o are each independently 1 or 2,
y is an integer of 0 to 8.
Preferably, the light emitting layer includes both the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 as host materials.
The compound represented by the above chemical formula 1 has the following characteristics: having an anthracene structure, the 9 th and 10 th positions of anthracene are substituted with an aromatic or heteroaromatic ring to have a small dipole moment value.
Preferably, Ar11And Ar12Each independently selected from phenyl, naphthyl, biphenyl, or the group Ar11And Ar12Unsubstituted or substituted by methyl or trimethylsilyl:
in the above, X1Is S or O.
Preferably, L11And L12Each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene.
Preferably, the compound represented by the above chemical formula 1 is any one compound selected from the following compounds:
the compound represented by the above chemical formula 1 can be produced by a production method as shown in the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, the definitions other than X are the same as those described above, and X is a halogen, more preferably bromine. The above-mentioned production method is a suzuki coupling reaction, which is a reaction for introducing a substituent at the 9-or 10-position of anthracene, and can be further embodied in the production examples described below.
The compound represented by the above chemical formula 2 has the following characteristics: having an anthracene structure, the 1 and 8 positions of anthracene are substituted with an aromatic ring or a heteroaromatic ring, and the 10 position is substituted with an aromatic ring or a heteroaromatic ring, thereby having a small dipole moment value.
Preferably, Ar21、Ar22And Ar23Each independently is selected from phenyl, dimethylphenyl, naphthyl, biphenyl, terphenyl, or any of the following groups:
in the above-mentioned groups, the compounds of formula,
X2is S, O, N (R)3) Or C (R)4)(R5)，
R3To R5Each independently is substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C6-60Aryl, or R4And R5Together form a substituted or unsubstituted C6-60And (4) an aryl group.
Preferably, Ar21And Ar22Are identical to each other.
Preferably, L21、L22And L23Each independently a single bond, phenylene, or naphthylene
Preferably, the compound represented by the above chemical formula 2 is any one compound selected from the following compounds:
the compound represented by the above chemical formula 2 can be produced by a production method as shown in the following reaction formula 2. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 2]
In the above reaction formula 2, the definitions other than X are the same as those described above, and X is a halogen, more preferably bromine. The above-mentioned production method is a suzuki coupling reaction, which is a reaction for introducing a substituent into the 1-, 8-or 10-position of anthracene, and can be further embodied in the production examples described later.
The organic light-emitting element other than the host material is not particularly limited as long as it can be used in an organic light-emitting element, and the respective configurations will be described below.
An anode and a cathode
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO Al or SNO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as PEDOT, polypyrrole, and polyaniline,but is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multi-layer structure material such as Al, but not limited thereto.
Hole injection layer
The organic light-emitting element according to the present invention may include a hole injection layer that injects holes from the electrode.
As the hole injecting substance, the following compounds are preferable: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer.
Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
Hole transport layer
The organic light-emitting element according to the present invention may further include a hole-transporting layer that receives holes from the anode or the hole-injecting layer and transports the holes to the light-emitting layer.
The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
Luminescent layer
The light-emitting layer of the organic light-emitting element according to the present invention may contain a dopant in addition to the host material.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,
And diindenopyrene (Periflanthene), and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
Preferably, as the above dopant, a compound represented by the following chemical formula 3 may be used:
[ chemical formula 3]
In the chemical formula 3 above, the first and second,
R1to R8Each independently hydrogen, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-10Cycloalkyl, substituted or unsubstituted silyl, cyano, or substituted or unsubstituted C6-30An aryl group, a heteroaryl group,
Ar1to Ar4Each independently is substituted or unsubstituted C6-30Aryl, or substituted or unsubstituted C containing more than one of O, N, Si and S2-60Heterocyclic group, but Ar1To Ar4Is represented by the following chemical formula 4:
[ chemical formula 4]
In the chemical formula 4 above, the first and second,
x is O or S, and X is O or S,
R9and R10Each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group.
Preferably, R1To R8Is hydrogen.
Preferably, Ar1And Ar3Is phenyl, Ar2And Ar4Is dibenzofuranyl.
Examples of the compound represented by the above chemical formula 3 are as follows:
electron transport layer
The organic light-emitting element according to the present invention may include an electron transport layer that receives electrons from the cathode or the electron injection layer and transports the electrons to the light-emitting layer.
The electron-transporting substance is a substance capable of receiving electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electronsIn (1). Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the usual substances having a low work function and accompanying an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are included in each of the substances, and are associated with an aluminum layer or a silver layer.
Electron injection layer
The organic light-emitting element according to the present invention may include an electron injection layer that injects electrons from the electrode.
As the electron-injecting substance, the following compounds are preferred: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability.
Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like thereof, but are not limited thereto. Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), and bis (10-hydroxybenzo [ h ] s]Quinoline) beryllium, bis (10-hydroxybenzo [ h ]]Quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but is not limited thereto.
Organic light emitting element
Fig. 1 to 3 show examples of the structure of the organic light-emitting device according to the present invention. Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, and a cathode 4.
Fig. 3 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, an electron injection layer 8, and a cathode 4.
The organic light-emitting device according to the present invention can be manufactured by sequentially stacking the above-described structures. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as sputtering or electron beam evaporation (e-beam evaporation) to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element. The light-emitting layer can be formed not only by a vacuum deposition method using a host material and a dopant but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to this method, an organic light-emitting element may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
The organic light-emitting element according to the present invention may be of a top emission type, a bottom emission type, or a bidirectional emission type, depending on the material used.
In the following, preferred embodiments are suggested to aid in understanding the present invention. However, the following examples are provided only for easier understanding of the present invention, and the contents of the present invention are not limited thereto.
Production example 1: production of Compound represented by chemical formula 1
Production examples 1 to 8
9-bromo-10-phenylanthracene (9-bromo-10-phenylanthracene) (A,10g,30.1mmol) and (4-phenylnaphthalen-1-yl) boronic acid ((4-phenylnaphthalen-1-yl) boronic acid) (B,9g,36.1mmol), Pd (t-Bu)3P)2(0.8g,0.15mmol) of K in 2M2CO3The aqueous solution (30mL) was stirred with THF (100mL) under reflux for about 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, dried over magnesium sulfate, distilled under reduced pressure, and recrystallized by Tol (toluene)/EA (ethyl acetate), whereby the compounds of production examples 1 to 8 (12.8g, 93%) were produced.
MS[M+]Measured (found)456.32, calculated (calc) 456.19
Production examples 1 to 18
The compounds of production examples 1 to 18 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-1-yl) anthracene (9-bromo-10- (naphthalene-1-yl) anthracene) was used in place of compound A and (4-phenylnaphthalene-2-yl) boronic acid was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.98
Production examples 1 to 20
The compounds of production examples 1 to 20 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-1-yl) anthracene (9-bromo-10- (naphthalene-1-yl) anthracene) was used in place of compound A and (4-phenylnaphthalene-1-yl) boronic acid ((4-phenylnaphthalene-1-yl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.22
Production examples 1 to 26
The compounds of production examples 1 to 26 were produced in the same manner as in production examples 1 to 8 except that 9-bromo-10- (naphthalene-1-yl) anthracene (9-bromo-10- (naphthalene-1-yl) anthracene) was used in place of compound A and (1,1 '-binaphthyl) -4-ylboronic acid ((1,1' -binapththalen) -4-ylboronic acid) was used in place of compound B.
MS[M+]Calculated value 556.22, measured value 556.09
Production examples 1 to 33
The compounds of production examples 1 to 33 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (4-phenylnaphthalene-2-yl) boronic acid was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.94
Production examples 1 to 34
The compounds of production examples 1 to 34 were produced in the same manner as in production examples 1 to 8 except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (1,1 '-binaphthyl) -4-ylboronic acid ((1,1' -binapththalen) -4-ylboronic acid) was used in place of compound B.
MS[M+]Calculated value 456.19, measured value 456.32
Production examples 1 to 35
The compounds of production examples 1 to 35 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (4- (naphthalene-1-yl) phenyl) boronic acid ((4- (naphthalene-1-yl) phenyl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.75
Production examples 1 to 36
The compounds of production examples 1 to 36 were produced in the same manner as in production examples 1 to 8 except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (6-phenylnaphthalene-2-yl) boronic acid was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.98
Production examples 1 to 38
The compounds of production examples 1 to 38 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (8-phenylnaphthalene-2-yl) boronic acid ((8-phenylnaphthalene-2-yl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.88
Production examples 1 to 43
The compounds of production examples 1 to 43 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (5-phenylnaphthalene-2-yl) boronic acid ((5-phenylnaphthalene-2-yl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 506.20, measured value 506.91
Production examples 1 to 73
The compounds of production examples 1 to 72 were produced in the same manner as in production examples 1 to 8 except that 9-bromo-10- (naphthalene-1-yl) anthracene (9-bromoo-10- (naphthalene-1-yl) anthracene) was used in place of compound A and indolo [3,2,1-jk ] carbazol-6-ylboronic acid (indolo [3,2,1-jk ] carbazol-6-ylboronic acid) was used in place of compound B.
MS[M+]Calculated value 543.20, measured value 543.69
Production examples 1 to 79
The compounds of production examples 1 to 79 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalen-1-yl) anthracene (9-bromo-10- (naphthalene-1-yl) anthracene) was used in place of compound A and (3- (5-phenylthiophen-2-yl) phenyl) boronic acid ((3- (5-phenylthiophen-2-yl) phenyl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 538.18, measured value 538.88
Production examples 1 to 81
The compounds of production examples 1 to 81 were produced in the same manner as in production examples 1 to 8, except that 9-bromo-10- (naphthalene-2-yl) anthracene (9-bromo-10- (naphthalene-2-yl) anthracene) was used in place of compound A and (3- (5-phenylthiophen-2-yl) phenyl) boronic acid ((3- (5-phenylthiophen-2-yl) phenyl) boronic acid) was used in place of compound B.
MS[M+]Calculated value 538.18, measured value 538.85
Production examples 1 to 86
The compounds of production examples 1 to 86 were produced by the same method as in production examples 1 to 8, except that 9- ([1,1'-biphenyl ] -4-yl) -10-bromoanthracene) (9- ([1,1' -biphenyl ] -4-yl) -10-bromoanthrene)) was used instead of compound a.
MS[M+]Calculated value 532.22, measured value 532.18
Production examples 1 to 87
The compounds of production examples 1 to 87 were produced in the same manner as in production examples 1 to 8 except that 9-bromo-10- (4- (naphthalen-1-yl) phenyl) anthracene (9-bromo-10- (4- (naphthalene-1-yl) phenyl) anthrylene) was used in place of compound A.
MS[M+]Calculated value 582.23, measured value 582.65
Production example 2: production of Compound represented by chemical formula 2
Production example 2-1
(step 1)
1, 8-dichloroanthraquinone (A',100g,360mmol) was dissolved in aqueous ammonia (4000L), and Zn powder (3000g) was added thereto, followed by stirring under reflux. After the reaction was completed, the reaction mixture was cooled to normal temperature, and after filtration, the organic layer was separated from the reaction filtrate, dried over magnesium sulfate, and after distillation under reduced pressure, recrystallized from hexane, the obtained solid was dissolved in isopropanol, and concentrated hydrochloric acid was added thereto, followed by stirring under reflux for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered, washed with water, and dried to obtain 1,8-dichloroanthracene (1,8-dichloroanthracene) (B',55.6g, 63%).
MS[M+]Calculated value 246.00, measured value 246.33
(step 2)
1,8-dichloroanthracene (1,8-dichloroanthracene) (B',10g,40.5mmol), dibenzo [ B, d ] and water are mixed together]Furan-4-ylboronic acid (dibenzo [ b, d ]]furan-4-ylboronic acid)(15.3g,89mmol)、Pd(dba)2(0.7g,1.22mmol)、PCy3(tricyclohexylphosphine, 0.67g,2.43mmol) was added to 2M K3PO4Aqueous solution (50mL) and THF (250mL) were stirred at reflux for about 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, dried over magnesium sulfate, distilled under reduced pressure, and recrystallized from THF/EtOH to obtain 1,8-bis (dibenzo [ b, d ]]Furan-4-yl) anthracene (1,8-bis (dibenzo [ b, d)]furan-4-yl)anthracene)(C',14g,68％)。
MS[M+]Calculated value 510.16, measured value 510.09
(step 3)
1,8-bis (dibenzo [ b, d ] furan-4-yl) anthracene (1,8-bis (dibenzo [ b, d ] furan-4-yl) anthracene) (C',14g,27.5mmol) was dissolved in chloroform (250mL), NBS (5.4g,30.3mmol) was added thereto at 0 ℃ and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solid produced in the reaction was filtered, washed with distilled water, and dried to obtain 4,4' - (10-bromoanthracene-1,8-diyl) dibenzo [ b, D ] furan (4,4' - (10-bromoanthracene-1,8-diyl) dibenzo [ b, D ] furan) (D ',13.0g, 85%).
MS[M+]Calculated value 588.07, measured value 588.21
(step 4)
4,4' - (10-bromoanthracene-1,8-diyl) di (dibenzo [ b, d)]Furan) (4,4' - (10-bromoantrhacene-1, 8-diyl) dibenzo [ b, d]furan) (D',10.0g,17.0mmol), naphthalen-1-ylboronic acid (3.22g,18.7mmol), Pd (t-Bu3) P2(0.43g,0.09mmol) were added to 2M K2CO3The aqueous solution (50mL) and THF (150mL) were stirred at reflux for about 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, dried over magnesium sulfate, distilled under reduced pressure, and recrystallized by Tol/EA to obtain Compound 2-1(10.1g, 93%) of production example.
MS[M+]Calculated value 636.21, measured value 635.52
Production example 2-2
In step 2 of production example 2-1, naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) was used in place of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid), and in step 4, dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) was used in place of naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid), thereby obtaining the compound of production example 2-2.
MS[M+]Calculated value 596.21, measured value 596.25
Production examples 2 to 3
In step 4 of production example 2-1, dibenzo [ b, d ] furan-4-yl boronic acid (dibenzo [ b, d ] furan-4-yl boronic acid) was used instead of naphthalene-1-yl boronic acid (naphthalene-1-yl boronic acid), thereby producing the compound of production example 2-3.
MS[M+]Calculated value 676.20, measured value 676.51
Production examples 2 to 10
In step 4 of production example 2-1, phenyl boronic acid (phenylboronic acid) was used instead of naphthalen-1-ylboronic acid (naphthalene-1-ylboronic acid), thereby obtaining the compound of production example 2-10.
MS[M+]Calculated value 586.19, measured value 586.33
Production examples 2 to 45
Production example 2-45 was produced by using naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) in place of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 of production example 2-1 and phenylboronic acid (phenylboronic acid) in place of naphthalene-1-ylboronic acid in step 4.
MS[M+]Calculated value 506.20, measured value 506.88
Production examples 2 to 46
Production example 2-46 was produced by using naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) in place of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 and (1,1'-biphenyl) -2-ylboronic acid ((1,1' -biphenyl)2-ylboronic acid) in place of naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) in step 4.
MS[M+]Calculated value 582.23, measured value 582.51
Production examples 2 to 47
Production example 2-47 was produced by using (3,5-dimethylphenyl) boronic acid ((3,5-dimethylphenyl) boronic acid) instead of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 of production example 2-1 and phenylboronic acid (phenylboronic acid) instead of naphthalene-1-ylboronic acid in step 4.
MS[M+]Calculated value 462.23, measured value 462.38
Production examples 2 to 48
Production example 2-48 was produced by using (3,5-dimethylphenyl) boronic acid ((3,5-dimethylphenyl) boronic acid) instead of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 of production example 2-1 and (1,1'-biphenyl)2-ylboronic acid ((1,1' -biphenyl)2-ylboronic acid) instead of naphthalene-1-ylboronic acid in step 4.
MS[M+]Calculated value 538.27, measured value 538.30
Production examples 2 to 49
In step 4 of production example 2-1, (1,1'-biphenyl)2-ylboronic acid ((1,1' -biphenyl)2-ylboronic acid) was used in place of naphthalen-1-ylboronic acid, thereby obtaining the compounds of production examples 2-49.
MS[M+]Calculated value 662.22, measured value 662.42
Production examples 2 to 50
Production example 2-50 was prepared using naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) instead of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 of production example 2-1.
MS[M+]Calculated value 556.22, measured value 556.63
Production examples 2 to 51
Production example 2-51 was produced by using (9,9-diphenyl-9H-fluoren-4-yl) boronic acid ((9, 9-diphenyl-9H-fluoro-4-yl) boronic acid) instead of dibenzo [ b, d ] furan-4-ylboronic acid (dibenzo [ b, d ] furan-4-ylboronic acid) in step 2 of production example 2-1 and phenyl boronic acid 5(phenylboronic acid) instead of naphthalene-1-ylboronic acid (naphthalene-1-ylboronic acid) in step 4.
MS[M+]Calculated value 886.36, measured value 886.11
Production examples 2 to 52
Production example 2-52 was produced by using (9,9-diphenyl-9H-fluoren-4-yl) boronic acid ((9, 9-diphenyl-9H-fluoro-4-yl) boronic acid) instead of dibenzo [ b, d ] furan-4-yl boronic acid in step 2 of production example 2-1 and dibenzo [ b, d ] furan-4-yl boronic acid in step 4 instead of naphthalene-1-yl boronic acid in step 1.
MS[M+]Calculated value 976.37, measured value 976.22
Production examples 2 to 53
Production example 2-53 was prepared by using dibenzo [ b, d ] furan-1-yl boronic acid (dibenzo [ b, d ] furan-1-yl boronic acid) instead of dibenzo [ b, d ] furan-4-yl boronic acid (dibenzo [ b, d ] furan-4-yl boronic acid) in step 2 of production example 2-1.
MS[M+]Calculated value 636.21, measured value 636.31
Production examples 2 to 54
In step 2 of production example 2-1, (3- (dibenzo [ b, d ] furan-4-yl) phenyl) boronic acid was used instead of dibenzo [ b, d ] furan-4-yl boronic acid (3- (dibenzo [ b, d ] furan-4-yl) phenyl) boronic acid, thereby producing the compound of production example 2-54.
MS[M+]780.30 found, calculated 788.27
In addition to the compounds produced in the above production examples, the structures of the compounds used in the following examples are as follows.
Example 1
A glass substrate coated with ITO (indium tin oxide) in a thin film of 150nm thickness was placed in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, a product of fisher (Fischer Co.) was used as the lotion, and distilled water was filtered twice with a Filter (Filter) manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated 2 times with distilled water for 10 minutes. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with nitrogen plasma for 5 minutes, the substrate was transported to a vacuum evaporator. The following HAT-CN compound was thermally vacuum-deposited on the ITO transparent electrode prepared as described above to a thickness of 5nm to form a hole injection layer. Next, HTL1 was thermally vacuum-evaporated at a thickness of 100nm, and HTL2 was thermally vacuum-evaporated at a thickness of 10nm, thereby forming a hole transporting layer. Next, BH1 as a host material and BD (weight ratio 95:5) as a dopant were simultaneously vacuum-evaporated to form a light-emitting layer with a thickness of 20 nm. Next, ETL was vacuum-evaporated to a thickness of 20nm to form an electron transport layer. Then, LiF was deposited in a vacuum with a thickness of 0.5nm to form an electron injection layer. Next, aluminum was deposited to a thickness of 100nm to form a cathode, thereby manufacturing an organic light emitting element.
Examples 2 to 63 and comparative examples 1 to 7
Organic light-emitting elements were produced by the same method as in example 1 above, but using the substances and contents shown in tables 1 and 2 below as host materials and dopants. 1-13, 2-1, etc. of substances corresponding to tables 1 and 2 below indicate that the compounds produced in the respective production examples were used, and the EML total DM was calculated by summing values obtained by multiplying dipole moment values of the respective host materials and dopants by contents.
[ TABLE 1]
[ TABLE 2]
Examples of the experiments
The characteristics of the organic light emitting elements produced in the above examples and comparative examples were evaluated, and the results are shown in tables 3 and 4.
[ TABLE 3]
[ TABLE 4]
Fig. 3 shows emission spectra of the organic light-emitting devices of example 1, example 2, and comparative example 1.
As shown in fig. 4, the total DM of the light emitting layers of example 1 and example 2 were 0.09 and 4.47, respectively, and the total DM of the light emitting layer of comparative example 1 was 4.93. The maximum peak positions of the respective spectra were 458nm, 464nm, 476nm in the order of example 1, example 2, and comparative example 1, respectively, and as the DM of the entire light emitting layer increased, the spectra shifted to the long wavelength side, and the FWHM sharply increased when the dipole moment value of the host material exceeded 4.5. When the colors of the above spectra are expressed by (CIE _ x, CIE _ y) using the CIE 1931 color space (CIE 1931 color space), example 1, example 2 and comparative example 1 are (0.137,0.092), (0.131,0.152) and (0.156,0.22), respectively, and it can be confirmed that, when the dipole moment value of the host material exceeds 4.5, the spectrum shifts to a long wavelength and the color purity is rapidly deteriorated by an increase in FWHM.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole transport layer 6: electron transport layer
7: hole injection layer 8: electron injection layer
Claims (9)
1. An organic light-emitting element comprising: an anode, a cathode, and a light-emitting layer between the anode and the cathode,
the light-emitting layer contains n kinds of substances different from each other,
wherein n is 4, at least one of the n species is a light emitting dopant,
the n substances satisfy the following mathematical formula 2:
mathematical formula 2
In the above-mentioned mathematical formula 2,
DMirepresenting the values of the dipole moments of the respective substances,
Airepresents a value obtained by dividing the weight of each substance by the total weight of the n substances,
the light-emitting layer contains, as host materials, both a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
Ar11and Ar12Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing at least one heteroatom selected from N, O and S2-60(ii) a heteroaryl group, wherein,
L11and L12Each independently is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
R1each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group,
h and i are each independently 1 or 2,
x is an integer of 0 to 8,
chemical formula 2
In the chemical formula 2, the first and second organic solvents,
Ar21、Ar22and Ar23Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing at least one heteroatom selected from N, O and S2-60(ii) a heteroaryl group, wherein,
L21、L22and L23Each independently is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
R2each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group,
m, n and o are each independently 1 or 2,
y is an integer from 0 to 8, excluding 8.
2. The organic light-emitting element according to claim 1, wherein Ar11And Ar12Each independently selected from phenyl, naphthyl, biphenyl, or the group Ar11And Ar12Unsubstituted or substituted by methyl or trimethylsilyl,
in the group, X1Is S or O.
3. The organic light-emitting element according to claim 1, wherein L11And L12Each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene.
4. The organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 1 is any one compound selected from the following compounds:
5. the organic light-emitting element according to claim 1, wherein Ar21、Ar22And Ar23Each independently is selected from phenyl, dimethylphenyl, naphthyl, biphenyl, terphenyl, or any of the following groups:
in the said group, the said group is,
X2is S, O, N (R)3) Or C (R)4)(R5)，
R3To R5Each independently is substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C6-60Aryl, or R4And R5Together form a substituted or unsubstituted C6-60And (4) an aryl group.
6. The organic light-emitting element according to claim 1, wherein Ar21And Ar22Are identical to each other.
7. The organic light-emitting element according to claim 1, wherein L21、L22And L23Each independently a single bond, phenylene, or naphthylene.
8. The organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 2 is any one compound selected from the following compounds:
9. the organic light-emitting element according to claim 1, wherein the light-emitting layer contains a compound represented by the following chemical formula 3 as a dopant,
chemical formula 3
In the chemical formula 3, the first and second organic solvents,
R1to R8Each independently hydrogen, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-10Cycloalkyl, substituted or unsubstituted silyl, cyano, or substituted or unsubstituted C6-30An aryl group, a heteroaryl group,
Ar1to Ar4Each independently is substituted or unsubstituted C6-30Aryl, or substituted or unsubstituted C containing more than one of O, N, Si and S2-60Heterocyclic group, but Ar1To Ar4Is represented by the following chemical formula 4:
chemical formula 4
In the chemical formula 4, the first and second organic solvents,
x is O or S, and X is O or S,
R9and R10Each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryloxy, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted amine, substituted or unsubstituted silyl, or substituted or unsubstituted C comprising more than one of O, N, Si and S2-60A heterocyclic group.
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| KR1020160174931A KR102145024B1 (en) | 2016-12-20 | 2016-12-20 | Organic light emitting device |
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| PCT/KR2017/009096 WO2018117369A1 (en) | 2016-12-20 | 2017-08-21 | Organic light emitting element |
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| CN108997345A (en) * | 2018-08-20 | 2018-12-14 | 上海大学 | A kind of azaspiro compounds, their and the organic electro-optic device containing the compound |
| WO2020075759A1 (en) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Organic electroluminescence element and electronic device using same |
| WO2020080714A1 (en) | 2018-10-16 | 2020-04-23 | 주식회사 엘지화학 | Organic compound and organic light-emitting device comprising same |
| JP7187095B2 (en) * | 2019-02-20 | 2022-12-12 | エルジー・ケム・リミテッド | Anthracene derivative having dibenzofuran-1-yl or dibenzothiophen-1-yl group and organic electronic device using the same |
| WO2020209293A1 (en) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Organic electroluminescent element and electronic device including same |
| WO2020209309A1 (en) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Organic electroluminescent element, and electronic device comprising same |
| CN113631547A (en) * | 2019-04-08 | 2021-11-09 | 出光兴产株式会社 | Organic electroluminescent element and electronic device using the same |
| US20220165965A1 (en) * | 2019-04-08 | 2022-05-26 | Idemitsu Kosan Co.,Ltd. | Organic electroluminescence device and electronic apparatus provided with the same |
| US20220173335A1 (en) * | 2019-04-08 | 2022-06-02 | Idemitsu Kosan Co.,Ltd. | Organic electroluminescence device and electronic apparatus equipped with the same |
| KR102427162B1 (en) * | 2019-11-11 | 2022-07-29 | 주식회사 엘지화학 | Organic light emitting device |
| US20220393110A1 (en) * | 2019-12-26 | 2022-12-08 | Idemitsu Kosan Co.,Ltd. | Organic electroluminescence element, composition, powder, electronic equipment, and novel compound |
| US20240122063A1 (en) * | 2021-01-26 | 2024-04-11 | Idemitsu Kosan Co.,Ltd. | Composition, powder, organic electroluminescent element, method for manufacturing organic electroluminescent element, and electronic device |
| CN113666929B (en) * | 2021-09-08 | 2023-04-07 | 南京高光半导体材料有限公司 | Carbazole fluorene spiro-compound and organic electroluminescent device |
| CN115611873A (en) * | 2022-12-20 | 2023-01-17 | 吉林省元合电子材料有限公司 | Organic photoelectric functional material containing benzimidazole and anthracene combined structure and application thereof |
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