CN110050357B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN110050357B CN110050357B CN201880004821.9A CN201880004821A CN110050357B CN 110050357 B CN110050357 B CN 110050357B CN 201880004821 A CN201880004821 A CN 201880004821A CN 110050357 B CN110050357 B CN 110050357B
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- emitting device
- organic light
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- UPIADLCYNMJMKP-UHFFFAOYSA-N spiro[1-azapentacyclo[10.7.1.02,7.08,20.014,19]icosa-2,4,6,8(20),9,11,14,16,18-nonaene-13,9'-fluorene]-2'-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC3=C2N1C1=CC=CC=C1C31C2=CC=CC=C2C2=CC=C(B(O)O)C=C21 UPIADLCYNMJMKP-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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Abstract
The present invention relates to an organic light emitting device excellent in driving voltage, light emitting efficiency, and lifetime.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2017-0153332, 11/16/2017, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to an organic light emitting device excellent in driving voltage, light emitting efficiency, and lifetime.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of 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 device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Problem to be solved
The invention provides an organic light emitting device with excellent driving voltage, light emitting efficiency and service life.
Means for solving the problems
In order to solve the above problems, the present invention provides an organic light emitting device, comprising: an anode, a light-emitting layer, a hole blocking layer, and a cathode, wherein the hole blocking layer contains a compound represented by the following chemical formula 1, and the light-emitting layer contains a compound represented by the following chemical formula 2:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 and L 2 Bonding with the positions 1 and 2 of naphthalene or bonding with the positions 2 and 1 of naphthalene respectively,
L 1 is substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heteroarylene group,
L 2 is a bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heteroarylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heteroaryl group, which is a group,
Ar 3 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heteroaryl group, which is a group,
wherein Ar is 3 Does not have pyridine, quinoline, isoquinoline, phenanthridine, benzo [ f ]]Quinoline, benzo [ f]Isoquinoline, benzo [ h ]]Quinoline, or benzo [ h ]]An isoquinoline structure of the present invention,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
Ar' 1 and Ar' 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heteroaryl group, which is a group,
R' 1 and R'. 2 Each independently is hydrogen; deuterium; halogen; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising a heteroatom selected from any one or more of N, O and S 2-60 A heteroaryl group, which is a group,
a and b are each independently integers from 0 to 4.
ADVANTAGEOUS EFFECTS OF INVENTION
The organic light emitting device according to the present invention can achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in the organic light emitting device by using the compound represented by chemical formula 1 and the compound represented by chemical formula 2 described above.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, a hole blocking layer 4, and a cathode 5.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, a light-emitting layer 3, a hole blocking layer 4, an electron transport layer 8, an electron injection layer 9, and a cathode 5.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,represents a bond to other substituents.
As used herein, the term "substituted or unsubstituted" refers to a substituted or unsubstituted radical selected from deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthioAlkylthio) aryl groupThio (/ -> Aryl thio), alkylsulfonylAlkylsulfoxy), arylsulfonyl (++>Aryl sulfoxy), silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, or 1 or more substituents in a heterocyclic group containing 1 or more of N, O and S atoms, or a substituent bonded with 2 or more substituents among the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen 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 a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, 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 above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are 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, but the present invention is not limited thereto.
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 phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the fluorenyl group may be substituted,the 2 substituents may combine with each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be thatEtc. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, si and S as a hetero atom, 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, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, or alkylamino group is the same as the above-mentioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the examples of alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In the present specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
The present invention provides an organic light-emitting device comprising an anode, a light-emitting layer, a hole blocking layer, and a cathode, wherein the hole blocking layer comprises a compound represented by the above chemical formula 1, and the light-emitting layer comprises a compound represented by the above chemical formula 2.
The organic light emitting device according to the present invention is characterized in that the material contained in the hole blocking layer and the light emitting layer is adjusted to adjust the energy level between the respective layers, thereby enabling to improve the driving voltage, efficiency, and lifetime.
The present invention will be described in detail below with respect to each component, and the order from anode to cathode will be described.
Anode
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected 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), indium Zinc Oxide (IZO), and the like; such as ZnO, al or SnO 2 A combination of metals such as Sb and oxides; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene)]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
Hole injection layer
The organic light emitting device according to the present invention may further include a hole injection layer on the anode. The hole injection layer is composed of a hole injection substance, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability.
The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
Hole transport layer
The organic light emitting device according to the present invention may further include a hole transport layer on the anode or the hole injection layer. The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transport the holes to the light-emitting layer, and a substance having a large hole mobility is suitable.
Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
Light-emitting layer
The organic light emitting device according to the present invention includes a light emitting layer on the anode, the hole injection layer, or the hole transport layer.
The light-emitting layer may include a host and a dopant, and in the present invention, the compound represented by the chemical formula 2 is used as the host.
In the above chemical formula 2, ar 'is preferably' 1 Is naphthyl, phenanthryl, dibenzofuranyl, or a substituent represented by the following formula:
in the above chemical formula, a is a benzene ring condensed with two adjacent rings.
Preferably, ar 'as described above' 1 Is naphthyl, phenanthryl, dibenzofuranyl, or a substituent represented by the following formula:
preferably Ar' 2 Is biphenyl, terphenyl, naphthylphenyl, or phenanthrylphenyl.
Preferably, R' 1 And R'. 2 Is hydrogen.
Preferably, the compound represented by the above chemical formula 2 is any one selected from the following compounds:
the compound represented by the above chemical formula 2 can be produced by the following production method of the reaction formula 2.
[ reaction type 2]
In the above reaction formula 2, the definitions other than X '"are the same as those described above, and X'" represents a substituent for suzuki coupling reaction, preferably halogen, more preferably bromine or chlorine. The reaction represents a suzuki coupling reaction, and the production method can be more specifically described in the production examples described below.
Examples of the dopant include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. In particular, in the present invention, as the dopant, a compound represented by the following chemical formula 3 may be used.
[ chemical formula 3]
In the above-mentioned chemical formula 3,
l' is substituted or unsubstituted C 6-60 An arylene group,
Ar" 1 to Ar' 4 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 Heteroaryl groups.
Preferably, L "is any one selected from the following groups:
of the above-mentioned groups, the group,
r' are each independently hydrogen, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 3-60 Cycloalkyl groups. More preferably, R' are the same as each other and are hydrogen, isopropyl, or cyclopentyl.
Preferably Ar' 1 And Ar' 4 Is dibenzofuranyl.
Preferably Ar' 2 And Ar' 3 Phenyl group, which is unsubstituted or substituted by C 1-60 Alkyl, tri (C) 1-60 ) Alkylsilyl, or phenyl substitution.
Preferably, the compound represented by the above chemical formula 3 is any one selected from the following compounds:
/>
hole blocking layer
The organic light emitting device according to the present invention includes a hole blocking layer on the above light emitting layer. The hole blocking layer prevents holes injected from the anode from being transferred to the electron transport layer without being recombined in the light emitting layer.
In particular, in the present invention, the compound represented by the above chemical formula 1 is used in the above hole blocking layer.
In the above chemical formula 1, L 1 And L 2 Bonding to positions 1 and 2 of naphthalene, or bonding to positions 2 and 1 of naphthalene, respectively, and accordingly, may be represented by the following chemical formula 1-1 or 1-2:
[ chemical formula 1-1]
[ chemical formulas 1-2]
Preferably L 1 Is phenylene. More preferably L 1 Is 1, 3-phenylene or 1, 4-phenylene.
Preferably L 2 Is a bond or phenylene. More preferably L 2 Is a bond, 1, 3-phenylene, or 1, 4-phenylene.
Preferably Ar 1 Is phenyl.
Preferably Ar 2 Is phenyl or biphenyl.
Preferably Ar 3 Is any one selected from the following groups:
of the above-mentioned groups, the group,
x is NR 1 、CR 2 R 3 、SiR 4 R 5 S, or O,
R 1 to R 8 Each independently is hydrogen; deuterium; halogen; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one of O, N, si and S 2-60 A heterocyclic group,
n, m and l are each independently integers from 0 to 4.
More preferably Ar 3 Is any one selected from the following groups:
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more preferably Ar 3 L is the above (a), (b), or (c) 2 Is a bond; or Ar 3 L is the above (d), (f), (g), or (h) 2 Is 1, 4-phenylene; or Ar 3 In the above (e), L 2 Is a bond, 1, 3-phenylene, or 1, 4-phenylene.
The compound represented by the above chemical formula 1 may be selected from the following compounds.
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The compound represented by the above chemical formula 1 can be produced by the following production method of the chemical formula 1.
[ reaction type 1]
In the above reaction scheme 1, L 1 、L 2 、Ar 1 、Ar 2 And Ar is a group 3 As defined above, X' and X "represent substituents for the bell wood coupling reaction. The step 1 or the step 1' represents a suzuki coupling reaction, and the production method may be more specifically described in the production examples described later.
Electron transport layer
The organic light emitting device according to the present invention may include an electron transport layer on the hole blocking layer. The electron transporting layer is a layer that receives electrons from the cathode or an electron injecting layer formed on the cathode and transports the electrons to the light emitting layer, and as an electron transporting substance, a substance that can well inject electrons from the cathode and transfer the electrons to the light emitting layer is preferable, and a substance having a large electron mobility is preferable.
As a specific example of the electron transporting substance, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular the number of the active ingredients,examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium are each accompanied by an aluminum layer or a silver layer.
Electron injection layer
The organic light emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the cathode. The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect 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 has an excellent thin film forming ability.
Specific examples of the substance that can be used as the electron injection layer include fluorenone, anthraquinone dimethane (anthraquinone), diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives. />
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
Cathode electrode
As the cathode material, a material having a small work function is generally preferred in order to facilitate electron injection into the organic layer. As a means ofSpecific 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; such as LiF/Al or LiO 2 And/or Al, but is not limited thereto.
Organic light emitting device
The organic light emitting device according to the present invention can be manufactured by sequentially laminating the above-described constitution. At this time, it can be manufactured as follows: a PVD (Physical Vapor Deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The host and the dopant of the light-emitting layer may be formed not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
On the other hand, the organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In the following, preferred embodiments are presented to aid in understanding the present invention. However, the following examples are provided for easier understanding of the present invention, and the present invention is not limited thereto.
Production example
Production example 1: production of Compound 1
(step 1)
1-bromonaphthalen-2-ol (20.0 g,89.7 mmol), 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine (50.0 g,94.1 mmol) and potassium carbonate (24.8 g,179.3 mmol) were added and stirred with heating. After refluxing, tetrakis (triphenylphosphine) palladium (0) (1.2 g,1.0 mmol) was added and stirred for a further 5 hours with heating. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the resultant was washed with ethanol to give compound 1-a (39 g, yield 96%).
MS:[M+H] + ＝452
(step 2)
Compound 1-A (39 g,86.4 mmol) and potassium carbonate (23.9 g,172.7 mmol) were added to 300mL of acetonitrile solvent and heated to 50 ℃. After stirring for 30 minutes, 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride (39.1 g,129.6 mmol) was added, and the temperature was lowered to room temperature and further stirred for 1 hour. After the reaction was completed, the mixture was filtered 1 time to remove impurities. Compound 1-B was then produced by ethanol slurry (60 g, yield 95%).
MS:[M+H] + ＝734
(step 3)
Compound 1-B (50 g,68.2 mmol), (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid (25.9 g,71.6 mmol) and potassium carbonate (18.8 g,136.3 mmol) were added to 400mL of tetrahydrofuran solvent and heated with stirring. After refluxing, tetrakis (triphenylphosphine) palladium (0) (2.4 g,2.0 mmol) was added and stirred with heating for 6 hours. The reaction solution was cooled and filtered, and then purified by EtOH slurry to give compound 1 (47 g, yield 91.7%).
MS:[M+H] + ＝752
Production example 2: production of Compound 3
Compound 3 was produced by the same method as that for compound 1, except that 9,9' -spirodi [ fluoren ] -2-ylboronic acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝750
Production example 3: production of Compound 5
Compound 5 was produced by the same method as that for compound 1, except that spiro [ fluorene-9, 8' -indolo [3,2,1-de ] acridin ] -2-yl boronic acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝839
Production example 4: production of Compound 7
Compound 7 was produced by the same method as the production method of compound 1, except that triphenylene-2-yl boric acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boric acid.
MS:[M+H] + ＝662
Production example 5: production of Compound 9
(step 1)
1-bromonaphthalen-2-ol (20.0 g,89.7 mmol) and (4- (triphenylen-2-yl) phenyl) boronic acid (31.2 g,89.7 mmol) were added and potassium carbonate (24.8 g,179.3 mmol) was heated with stirring. After refluxing, tetrakis (triphenylphosphine) palladium (0) (3.1 g,2.6 mmol) was added and stirred for 3 hours with further heating. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, washing with ethanol, compound 9-a was produced (38 g, yield 95%).
MS:[M+H] + ＝447
(step 2)
Compound 9-B was produced by the same method as that for compound 1-B except that compound 9-a was used instead of compound 1-a.
MS:[M+H] + ＝729
(step 3)
/>
Compound 9 was produced by the same method as the production method of compound 1, except that compound 9-B was used instead of compound 1-B, and 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝738
Production example 6: production of Compound 11
(step 1)
1-bromonaphthalen-2-ol (20.0 g,89.7 mmol), triphenylen-2-ylboronic acid (24.4 g,89.7 mmol) and potassium carbonate (24.8 g,179.3 mmol) were added and stirred with heating. After refluxing, tetrakis (triphenylphosphine) palladium (0) (3.1 g,2.6 mmol) was added and stirred for 3 hours with further heating. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the compound 11-A was produced by washing with ethanol (30 g, yield 91%).
MS:[M+H] + ＝371
(step 2)
Compound 11-B was produced by the same method as that of Compound 1-B, except that Compound 11-A was used instead of Compound 1-A.
MS:[M+H] + ＝653
(step 3)
/>
Compound 11-B (50 g,76.6 mmol), 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine (33.4 g,76.6 mmol), potassium carbonate (20.3 g,153.2 mmol) and tetrakis (triphenylphosphine) palladium (0) (2.7 g,2.3 mmol) were added and heated and stirred for 4 hours. After the completion of the reaction, the reaction solution was cooled and filtered, followed by purification by EtOH slurry, whereby compound 11 (47 g, yield 93%) was obtained.
MS:[M+H] + ＝662
Production example 7: production of Compound 13
(step 1)
Compound 13-a was produced by the same method as compound 1-a except that 2, 4-diphenyl-6- (3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine was used instead of 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine.
MS:[M+H] + ＝452
(step 2)
Compound 13-B was produced by the same method as that of Compound 1-B, except that Compound 13-A was used instead of Compound 1-A.
MS:[M+H] + ＝734
(step 3)
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Compound 13 was produced by the same method as that of compound 1 except that compound 13-B was used instead of compound 1-B, and (9, 9-diphenyl-9H-fluoren-4-yl) boric acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boric acid.
MS:[M+H] + ＝752
Production example 8: production of Compound 14
Compound 14 was produced by the same method as compound 13, except that 9,9' -spirodi [ fluoren ] -2-yl boronic acid was used instead of (9, 9-diphenyl-9H-fluoren-4-yl) boronic acid.
MS:[M+H] + ＝750
Production example 9: production of Compound 18
Compound 18 was produced by the same method as compound 13, except that [1,1' -biphenyl ] -4-ylboronic acid was used instead of (9, 9-diphenyl-9H-fluoren-4-yl) boronic acid.
MS:[M+H] + ＝588
Production example 10: production of Compound 19
Compound 19 was produced by the same method as compound 7, except that compound 13-B was used instead of compound 1-B.
MS:[M+H] + ＝662
Production example 11: production of Compound 50
(step 1)
Use of 2- ([ 1,1' -biphenyl ] -3-yl) -4-phenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine instead of 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine, except for this, compound 50-A was produced by the same method as that of compound 1-A.
MS:[M+H] + ＝528
(step 2)
Compound 50-B was produced by the same method as compound 1-B except that compound 50-a was used instead of compound 1-a.
MS:[M+H] + ＝810
(step 3)
Compound 50 was produced by the same method as compound 1, except that (4- (9H-carbazol-9-yl) phenyl) boronic acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝753
Production example 12: production of Compound 66
Compound 66 was produced by the same method as compound 1 except that 4, 5-tetramethyl-2- (4- (7-phenyl-7H-benzo [ c ] fluoren-7-yl) phenyl) -1,3, 2-dioxaborolan was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝802
Production example 13: production of Compound 82
Compound 82 was produced by the same method as compound 1, except that (4- (phenanthryl-2-yl) phenyl) boronic acid was used instead of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid.
MS:[M+H] + ＝688
Production example 14: production of Compound A
2-bromodibenzofuran (15 g,60.7 mmol), (10-phenylanthracen-9-yl) boric acid (18.1 g,60.7 mmol) and potassium carbonate (25.1 g,182.1 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (2.1 g,3 mol%) was added, and further heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed, whereby compound a (19.9 g, yield 78%) was produced.
MS:[M+H] + ＝421
Production example 15: production of Compound B
3-bromodibenzofuran (15 g,60.7 mmol), (10-phenylanthracen-9-yl) boric acid (18.1 g,60.7 mmol) and potassium carbonate (25.1 g,182.1 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (2.1 g,3 mol%) was added and stirred for 7 hours with further heating. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above compound B was produced by recrystallization from ethanol (18.1 g, yield 71%).
MS:[M+H] + ＝421
Production example 16: production of Compound C
2-Bromonaphtho [2,3-b ] benzofuran (15 g,50.5 mmol), (10-phenylanthracen-9-yl) boronic acid (15.1 g,50.5 mmol) and potassium carbonate (20.9 g,151.4 mmol) are added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (1.7 g,3 mol%) was added, heated and stirred for a further 8 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was added to water, and the organic layer was extracted with chloroform to obtain an organic layer, which was then dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed, whereby the above-mentioned compound C (16.3 g, yield 69%) was produced.
MS:[M+H] + ＝471
Production example 17: production of Compound D
3-bromodibenzofuran (15 g,60.7 mmol), (10-phenylanthracen-9-yl) boric acid (18.1 g,60.7 mmol) and potassium carbonate (25.1 g,182.1 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (2.1 g,3 mol%) was added, heated and stirred for a further 5 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above compound D was produced by recrystallization from ethanol (20.2 g, yield 79%).
MS:[M+H] + ＝421
Production example 18: production of Compound E
4-bromo-1, 1' -biphenyl (10 g,42.9 mmol), (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (14.9 g,42.9 mmol) and potassium carbonate (17.8 g,128.7 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (1.4 g,3 mol%) was added, and further heated and stirred for 5 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above compound E was produced (16.1 g, yield 82%) by recrystallization from ethanol.
MS:[M+H] + ＝457
Production example 19: production of Compound F
2- (4-bromophenyl) naphthalene (10 g,35.3 mmol), (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (12.3 g,35.3 mmol) and potassium carbonate (14.6 g,105.9 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (1.2 g,3 mol%) was added, and further heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above compound F was produced (14.3 g, yield 80%) by recrystallization from ethanol.
MS:[M+H] + ＝507
Production example 20: production of Compound G
5' -bromo-1, 1':3',1 "-terphenyl (15 g,48.5 mmol), (10- (naphthalen-2-yl) anthracen-9-yl) boronic acid (16.9 g,48.5 mmol) and potassium carbonate (20.1 g,145.5 mmol) were added, heated and stirred. After refluxing, tetrakis (triphenylphosphine) palladium (0) (1.7 g,3 mol%) was added, heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then filtered 1 time to remove impurities. The filtrate was taken in water, extracted with chloroform to obtain an organic layer, which was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above compound G was produced by recrystallization from ethanol (17.1G, yield 66%).
MS:[M+H] + ＝533
Examples (example)
Example 1
Will be as followsThe glass substrate coated with ITO (indium tin oxide) was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. At this time, the detergent was prepared by using a fisher co product, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, it was subjected to ultrasonic washing with distilled water twice for 10 minutes. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. In addition, the oxygen plasma is utilized to carry outAfter the substrate was cleaned for 5 minutes, the substrate was transferred to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following compound HI-A was usedVacuum vapor deposition to form a hole injection layer. The following compounds HAT-CN +.>And the following compound HT-AVacuum evaporation is performed to form a hole transport layer. Next, the compound a manufactured previously and the compound BD described below were put on the above hole transport layer at a weight ratio of 25:1 by film thickness +.>Vacuum vapor deposition is performed to form a light-emitting layer. On the above-mentioned light-emitting layer, the previously produced compound 1 was used as +.>Vacuum vapor deposition to form a hole blocking layer. The following compounds ET-A and LiQ (8-hydroxyquinoline lithium ) were combined in a weight ratio of 2:1 on the above hole blocking layer to>An electron transport layer is formed by the thickness of (a). Lithium fluoride (LiF) is sequentially added to the electron transport layer>Is made of aluminum +.>The thickness was evaporated to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 Up to 5X 10 -8 The support is thus fabricated into an organic light emitting device.
Examples 2 to 26
An organic light-emitting device was manufactured in the same manner as in example 1 above, using the compounds described in table 1 below instead of the compound a and the compound 1, respectively.
Comparative examples 1 to 7
An organic light-emitting device was manufactured in the same manner as in example 1 above, using the compounds described in table 1 below instead of the compound a and the compound 1, respectively. In table 1 below, the compounds ET1, ET2, ET3, ET4, ET5 and ET6 are as follows, respectively.
Experimental example
The organic light-emitting device manufactured by the method was manufactured at 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 Is measured at a current density of 90% relative to the initial luminance (T 90 ). The results are shown in table 1 below.
[ Table 1]
| BH | HBL | Voltage (V) | Efficiency (cd/A) | Color coordinates (x, y) | T 90 (hr) | |
| Example 1 | Compound A | Compound 1 | 3.68 | 7.32 | (0.130,0.147) | 181 |
| Example 2 | Compound A | Compound 3 | 3.69 | 7.53 | (0.131,0.147) | 160 |
| Example 3 | Compound A | Compound 5 | 3.81 | 7.25 | (0.130,0.146) | 201 |
| Example 4 | Compound A | Compound 7 | 3.88 | 7.35 | (0.131,0.147) | 210 |
| Example 5 | Compound A | Compound 9 | 3.92 | 7.16 | (0.130,0.146) | 221 |
| Example 6 | Compound A | Compound 11 | 3.88 | 7.35 | (0.130,0.147) | 217 |
| Example 7 | Compound A | Compound 13 | 3.68 | 7.44 | (0.130,0.147) | 195 |
| Example 8 | Compound A | Compound 14 | 3.77 | 7.52 | (0.131,0.147) | 162 |
| Example 9 | Compound A | Compound 18 | 3.72 | 7.48 | (0.130,0.147) | 172 |
| Example 10 | Compound B | Compound 19 | 3.92 | 7.45 | (0.130,0.148) | 165 |
| Example 11 | Compound B | Compound 50 | 3.96 | 7.64 | (0.130,0.147) | 153 |
| Example 12 | Compound B | Compound 66 | 3.86 | 7.78 | (0.131,0.147) | 157 |
| Example 13 | Compound B | Compound 82 | 3.83 | 7.65 | (0.130,0.147) | 167 |
| Example 14 | Compound C | Compound 1 | 3.25 | 7.77 | (0.130,0.148) | 162 |
| Example 15 | Compound C | Compound 7 | 3.19 | 7.95 | (0.130,0.147) | 145 |
| Example 16 | Compound C | Compound 11 | 3.20 | 7.68 | (0.131,0.147) | 177 |
| Example 17 | Compound D | Compound 50 | 3.54 | 7.13 | (0.130,0.146) | 162 |
| Example 18 | Compound D | Compound 66 | 3.65 | 7.01 | (0.130,0.147) | 185 |
| Example 19 | Compound E | Compound 82 | 3.69 | 7.88 | (0.130,0.147) | 199 |
| Example 20 | Compound E | Compound 18 | 3.88 | 7.68 | (0.131,0.147) | 201 |
| Example 21 | Compound E | Compound 19 | 3.91 | 7.53 | (0.130,0.147) | 186 |
| Example 22 | Compound F | Compound 1 | 3.52 | 8.24 | (0.130,0.148) | 160 |
| Example 23 | Compound F | Compound 3 | 3.57 | 8.16 | (0.130,0.147) | 153 |
| Example 24 | Compound F | Compound 5 | 3.61 | 8.36 | (0.131,0.147) | 158 |
| Example 25 | Compound G | Compound 19 | 3.88 | 7.46 | (0.130,0.148) | 186 |
| Example 26 | Compound G | Compound 50 | 3.73 | 7.56 | (0.130,0.147) | 170 |
| Comparative example 1 | Compound A | ET1 | 4.21 | 6.25 | (0.130,0.147) | 132 |
| Comparative example 2 | Compound A | ET2 | 4.38 | 6.12 | (0.130,0.147) | 145 |
| Comparative example 3 | Compound A | ET3 | 3.92 | 6.01 | (0.131,0.147) | 112 |
| Comparative example 4 | Compound F | ET1 | 4.12 | 6.72 | (0.130,0.147) | 95 |
| Comparative example 5 | Compound F | ET4 | 4.42 | 6.35 | (0.130,0.148) | 120 |
| Comparative example 6 | Compound F | ET5 | 4.51 | 6.29 | (0.130,0.147) | 160 |
| Comparative example 7 | Compound F | ET6 | 4.20 | 6.51 | (0.130,0.147) | 135 |
Symbol description
1: substrate 2: anode
3: light emitting layer 4: hole blocking layer
5: cathode 6: hole injection layer
7: hole transport layer 8: electron transport layer
9: an electron injection layer.
Claims (11)
1. An organic light emitting device comprising:
an anode;
a light emitting layer;
a hole blocking layer; and
a cathode electrode, which is arranged on the surface of the cathode,
wherein the hole blocking layer comprises a compound represented by the following chemical formula 1, and
the light emitting layer includes a compound represented by the following chemical formula 2:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 and L 2 Bonding with the positions 1 and 2 of naphthalene respectively or bonding with the positions 2 and 1 of naphthalene respectively,
L 1 is C 6-60 An arylene group,
L 2 is a bond; or C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C 6-60 An aryl group,
Ar 3 is C 6-60 An aryl group; or C containing at least one of O, N, si and S 2-60 A heteroaryl group, which is a group,
provided that Ar is 3 Does not have pyridine, quinoline, isoquinoline, phenanthridine, benzo [ f ]]Quinoline, benzo [ f]Isoquinoline, benzo [ h ]]Quinoline, or benzo [ h ]]An isoquinoline structure of the present invention,
[ chemical formula 2]
In the chemical formula 2 described above, a compound having a structure of,
Ar' 1 is C 6-60 An aryl group; or C containing at least one of O, N, si and S 2-60 A heteroaryl group, which is a group,
Ar' 2 is C 6-60 An aryl group,
R' 1 and R'. 2 Each independently is hydrogen; or deuterium, or both,
a and b are each independently integers from 0 to 4.
2. The organic light-emitting device of claim 1, wherein L 1 Is phenylene.
3. The organic light-emitting device of claim 1, wherein L 2 Is a bond or phenylene.
4. The organic light-emitting device of claim 1, wherein Ar 1 Is phenyl.
5. The organic light-emitting device of claim 1, wherein Ar 2 Is phenyl or biphenyl.
6. The organic light-emitting device of claim 1, wherein Ar 3 Is any one selected from the following groups:
7. the organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
8. the organic light-emitting device of claim 1, wherein Ar' 1 Is naphthyl, phenanthryl, dibenzofuranyl, or a substituent represented by the following formula:
in the above chemical formula, a is a benzene ring condensed with two adjacent rings.
9. The organic light-emitting device of claim 1, wherein Ar' 2 Is biphenyl, triBiphenyl, naphthylphenyl, or phenanthrylphenyl.
10. The organic light-emitting device of claim 1, wherein R' 1 And R'. 2 Is hydrogen.
11. The organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 2 is any one selected from the group consisting of:
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| PCT/KR2018/014128 WO2019098766A1 (en) | 2017-11-16 | 2018-11-16 | Organic light-emitting device |
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| KR102568228B1 (en) * | 2019-11-05 | 2023-08-18 | 주식회사 엘지화학 | Organic light emitting device |
| WO2021091165A1 (en) * | 2019-11-05 | 2021-05-14 | 주식회사 엘지화학 | Organic light-emitting device |
| EP3828161A3 (en) | 2019-11-27 | 2021-07-07 | Samsung Display Co., Ltd. | Organic electroluminescence device and diamine compound for organic electroluminescence device |
| CN110963876A (en) * | 2019-12-20 | 2020-04-07 | 西安瑞联新材料股份有限公司 | Preparation and purification method of 9, 10-substituted anthracene |
| US20220109112A1 (en) * | 2020-05-29 | 2022-04-07 | Lg Display Co., Ltd. | Organic light emitting device |
| US20210384437A1 (en) * | 2020-05-29 | 2021-12-09 | Lg Display Co., Ltd. | Organic light emitting device |
| US20230165140A1 (en) * | 2020-06-03 | 2023-05-25 | Lg Chem, Ltd. | Compound and organic light-emitting device comprising same |
| CN112321585B (en) * | 2020-10-30 | 2022-04-22 | 华南理工大学 | Asymmetric substituted diphenyl pyridine compound and preparation and application thereof |
| KR102441537B1 (en) * | 2021-05-24 | 2022-09-07 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN116023344B (en) * | 2021-12-30 | 2024-03-08 | 江苏三月科技股份有限公司 | Compound containing triazine and spirofluorene structures and application of compound in organic electroluminescent device |
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