CN113454803B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN113454803B CN113454803B CN202080015228.1A CN202080015228A CN113454803B CN 113454803 B CN113454803 B CN 113454803B CN 202080015228 A CN202080015228 A CN 202080015228A CN 113454803 B CN113454803 B CN 113454803B
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- emitting device
- organic light
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
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- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- BKJULDLPGWGCHY-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-4-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(Br)C=C1 BKJULDLPGWGCHY-UHFFFAOYSA-N 0.000 description 1
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- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition 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
- 125000004434 sulfur atom Chemical group 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 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
- 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The present invention provides an organic light emitting device, including: an anode; a cathode provided opposite to the anode; a light-emitting layer provided between the anode and the cathode; an electron transport region provided between the anode and the light-emitting layer; and a hole transport region provided between the light-emitting layer and the cathode, wherein the hole transport region includes a first compound containing a tertiary amine, and the light-emitting layer includes a second compound containing a phenanthryl group.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2019-0055231, 5.10 a.2019, 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 having low driving voltage, high light emitting efficiency, and excellent lifetime.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy 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. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exciton) are formed, 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 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to an organic light emitting device having low driving voltage, high light emitting efficiency, and excellent lifetime.
Solution to the problem
In order to solve the above problems, the present invention provides the following organic light emitting device.
The organic light emitting device according to the present invention, wherein it comprises:
An anode;
A cathode provided opposite to the anode;
A light-emitting layer provided between the anode and the cathode;
A hole transport region provided between the anode and the light-emitting layer; and
An electron transport region is provided between the light-emitting layer and the cathode,
The hole transport region contains a first compound represented by the following chemical formula 1,
The light emitting layer includes a second compound represented by the following chemical formula 2,
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 to L 3 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
Ar 1 is substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
R 1 and R 2 are each independently hydrogen; deuterium; halogen; cyano group; a nitro group; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 1-60 haloalkyl; substituted or unsubstituted C 1-60 haloalkoxy; substituted or unsubstituted C 3-60 cycloalkyl; a substituted or unsubstituted C 2-60 alkenyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
A and b are each integers of 0 to 9,
[ Chemical formula 2]
In the above-mentioned chemical formula 2,
L 4 and L 5 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
Ar 2 and Ar 3 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
R 3 is substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
Effects of the invention
The above-described organic light emitting device includes a compound of a specific structure in each of the light emitting layer and the hole transport region, respectively, so that it can exhibit low driving voltage, high light emitting efficiency, and long life characteristics.
Drawings
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60.
Fig. 2 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole-transporting region 30, a light-emitting layer 40, an electron-transporting region 50, and a cathode 60, wherein the hole-transporting region 30 includes a hole-injecting layer 31, a hole-transporting layer 33, and an electron-blocking layer 35 laminated in this order from the anode 20, and the electron-transporting region 50 includes a hole-blocking layer 51, an electron-transporting layer 53, and an electron-injecting layer 55 laminated in this order from the light-emitting layer 40.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
And/>Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano 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; alkylthio group [ ]Alkyl thioxy) of the formula (i); arylthio (/ >) Aryl thioxy) of the formula (i); alkylsulfonyl [ ]Alkyl sulfoxy) of the formula (i); arylsulfonyl (/ >)Aryl sulfoxy) of the formula (i); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom, or a substituent linked with 2 or more substituents in 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 is preferably 1 to 40. Specifically, the group 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 group may be a group 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 is preferably 1 to 25. Specifically, the group 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 a 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 this specification, a fluorenyl group may be substituted, and 2 substituents may be combined 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 heteroaryl group is a heteroaryl group containing 1 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 heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl,/>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, 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 exemplified for the aryl group described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In this specification, alkenyl groups in aralkenyl groups are the same as those exemplified for the alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this 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, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
The present invention provides an organic light emitting device having the following structure:
An anode;
A cathode provided opposite to the anode;
A light-emitting layer provided between the anode and the cathode and containing the second compound;
a hole transport region including the first compound and provided between the anode and the light-emitting layer; and
An electron transport region is provided between the light-emitting layer and the cathode.
The present invention will be described in detail with reference to the following configurations.
Anode and cathode
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), and Indium Zinc Oxide (IZO); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of 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; a multilayer structure such as LiF/Al or LiO 2/Al, but not limited thereto.
Hole transport region
An organic light-emitting device according to the present invention includes a hole transport region that receives holes from an anode provided between the anode and a light-emitting layer and transports the holes to the light-emitting layer, the hole transport region including a first compound represented by chemical formula 1.
The above-described first compound has a tertiary amine structure substituted with 2 phenanthrene-9-groups, so that hole injection characteristics and migration characteristics of holes to the light emitting layer are excellent, and thus an organic light emitting device using the above-described first compound can exhibit low driving voltage and high efficiency.
Preferably, in the above chemical formula 1, L 1 to L 3 may each independently be a single bond, or any one selected from the following groups:
Of the above-mentioned groups, the group,
X 1 is O, S, N (C 6-20 aryl), C (C 1-4 alkyl) 2, or C (C 6-20 aryl) 2.
For example, X 1 is O, S, N (phenyl), C (methyl) 2, or C (phenyl) 2.
More preferably, each of L 1 to L 3 is independently a single bond, or any one selected from the following groups:
preferably, L 1 and L 2 may not be single bonds. Specifically, when L 1 is a single bond, L 2 is any one selected from the following groups, and when L 2 is a single bond, L 1 is any one selected from the following groups:
Preferably Ar 1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl or spirobifluorenyl,
Here, ar 1 may be unsubstituted; or substituted with 1 to 5 substituents each independently selected from deuterium, C 1-10 alkyl, and C 6-20 aryl.
Preferably, ar 1 is any one selected from the following groups:
Preferably, a and b are each 0, 1 or 2. In this case, when a and b are 2 or more, the structures in brackets are the same or different. More preferably, a and b are each 0 or 1.
More preferably, R 1 and R 2 are the same as each other, in which case R 1 and R 2 may both be hydrogen or may both be phenyl.
Preferably, the above first compound is represented by the following chemical formula 1-1:
[ chemical formula 1-1]
In the above-mentioned chemical formula 1-1,
L 1 to L 3、Ar1、R1 and R 2 are as defined in chemical formula 1 above.
Representative examples of the above first compounds are shown below:
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/>
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In this case, as an example, when R 1 and R 2 are the same as each other and a and b are the same as each other, the first compound can be produced by the production method shown in the following reaction formula 1.
[ Reaction type 1]
/>
In the above reaction formula 1, T is each independently halogen, preferably bromine or chlorine, and the definition of the other substituents is the same as the above description.
Specifically, the compound represented by the above chemical formula 1 is produced by a suzuki coupling reaction in combination with a starting material. Such a suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be varied according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
On the other hand, the hole transport region may be composed of a hole injection layer, a hole transport layer, and an electron blocking layer, which are stacked in this order from the anode. Preferably, the electron blocking layer is located at a position in contact with the light emitting layer, and the first compound is contained in the hole transporting layer or the electron blocking layer. More preferably, the first compound is contained in the electron blocking layer.
The organic layers will be described in detail below.
(Hole injection layer)
The hole injection layer is a layer that is located on the anode and injects holes from the anode, and contains a hole injection substance. As such a hole injection substance, the following compounds are preferable: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. In particular, it is suitable that the HOMO (highest occupied molecular orbital) of the hole-injecting substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer.
Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
(Hole transporting layer)
The hole transport layer is formed on the hole injection layer and functions to receive holes from the hole injection layer and transport the holes to the light emitting layer. The hole-transporting layer contains a hole-transporting substance, and as such a hole-transporting substance, a substance having a large mobility to holes, which can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer, is suitable.
Preferably, as the hole transporting substance, a first compound represented by the above chemical formula 1 is used. Alternatively, as the hole transporting material, an arylamine-based organic material, a conductive polymer, a block copolymer having both conjugated and unconjugated portions, or the like can be used, but the hole transporting material is not limited thereto.
(Electron blocking layer)
The electron blocking layer is preferably formed on the hole transport layer and is preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and increasing the probability of hole-electron bonding. The electron blocking layer contains an electron blocking substance, and as such an electron blocking substance, a substance having a stable structure such that electrons cannot flow out of the light emitting layer is preferable.
Preferably, as the electron blocking substance, a first compound represented by the above chemical formula 1 is used. Alternatively, an arylamine-based organic substance or the like may be used as the electron blocking material, but the electron blocking material is not limited thereto.
Light-emitting layer
The organic light-emitting device according to the present invention includes, as a host substance, an anthracene compound substituted at positions No.2, 9, and 10 as a second compound represented by the above chemical formula 2. In particular, the second compound has a structure in which the same or different substituents are introduced at positions 9 and 10 and the substituent is introduced at position 2, and is excellent in material stability as compared with a compound in which the substituent is not introduced at position 2, and therefore can contribute to improvement in lifetime characteristics when used in an organic light-emitting device.
Preferably, in the above chemical formula 2, L 4 and L 5 may each independently be a single bond, or any one selected from the following groups:
Of the above-mentioned groups, the group,
Y 1 is O, S, N (C 6-20 aryl), C (C 1-4 alkyl) 2, or C (C 6-20 aryl) 2.
For example, Y 1 is O, S, N (phenyl), C (methyl) 2, or C (phenyl) 2.
More preferably, L 4 and L 5 are each independently a single bond or phenylene.
Preferably, ar 2 and Ar 3 are each independently C 6-20 aryl, or C 2-60 heteroaryl comprising O or S. More preferably, ar 2 and Ar 3 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothiophenyl.
More preferably, ar 2 and Ar 3 are each independently phenyl, biphenyl, naphthyl or dibenzofuranyl.
Preferably, R 3 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl,
Wherein R 3 may be unsubstituted; or may be substituted with 1 to 5 substituents each independently selected from deuterium, C 1-10 alkyl, tri (C 1-4 alkyl) silyl, and C 6-20 aryl.
More preferably, R 3 is any one selected from the following groups:
Of the above-mentioned groups, the group,
Q is hydrogen, C 1-10 alkyl, si (C 1-4 alkyl) 3, or C 6-20 aryl,
Y 2 is O, S, N (C 6-20 aryl), C (C 1-4 alkyl) 2, or C (C 6-20 aryl) 2. For example, Q is hydrogen, tert-butyl, si (methyl) 3, phenyl, or naphthyl,
Y 2 is O, S, N (phenyl), C (methyl) 2, or C (phenyl) 2.
Preferably, the above second compound is represented by the following chemical formula 2-1 or 2-2:
[ chemical formula 2-1]
[ Chemical formula 2-2]
In the above chemical formulas 2-1 and 2-2,
L 5、Ar3 and R 3 are as defined above for chemical formula 2.
Representative examples of the above second compounds are shown below:
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In this case, the second compound may be produced by a production method shown in the following reaction scheme 2, as an example.
[ Reaction type 2]
In the above reaction formula 2, T is halogen, preferably bromine or chlorine, and the definition of other substituents is the same as the above description.
Specifically, the compound represented by the above chemical formula 2 is produced by introducing an R 3 substituent into a starting material by suzuki coupling reaction. Such a suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be varied according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
On the other hand, the light emitting layer may further include a dopant material. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like. Preferably, the light emitting layer may include iridium complex as a dopant material.
An organic light emitting device provided with a light emitting layer including the host material and the dopant material described above may exhibit a maximum wavelength (λ max) in an emission spectrum at about 400nm to about 500 nm. Therefore, the above organic light emitting device is a blue light emitting organic light emitting device.
Electron transport region
An organic light-emitting device according to the present invention includes an electron transport region provided between the light-emitting layer and a cathode. The electron transport region is a region for transporting electrons from the cathode to the light emitting layer, and generally includes an electron transport layer. Preferably, the electron transport region includes a hole blocking layer and an electron transport layer laminated in this order from the light emitting layer; a hole blocking layer, and an electron injection and transport layer; or a hole blocking layer, an electron transport layer, and an electron injection layer.
(Hole blocking layer)
The hole blocking layer is formed on the light emitting layer, and specifically, the hole blocking layer is provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by preventing excessive migration of holes and thereby increasing the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance, and as such a hole blocking substance, a substance having a stable structure such that holes cannot flow out from the light emitting layer is preferable.
As the hole blocking material, azine derivatives including triazines, triazole derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto. /(I)
(Electron transport layer)
The electron transport layer is formed between the light emitting layer and the cathode, preferably between the hole blocking layer and an electron injection layer described later, and functions to receive electrons from the electron injection layer and transport the electrons to the light emitting layer. The electron transporting layer contains an electron transporting substance, and such an electron transporting substance is preferably a substance that can satisfactorily receive electrons from the cathode and transfer them to the light emitting layer, and has a large mobility for electrons.
Specific examples of the electron-transporting substance include, but are not limited to, pyridine derivatives, pyrimidine derivatives, triazole derivatives, triazine derivatives, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, and the like.
The electron transport layer may contain the electron transport material and the metal complex. 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).
(Electron injection layer)
The electron injection layer is located between the electron transport layer and the cathode, and functions to inject electrons from the cathode. The electron injection layer contains an electron injection substance, and as such an electron injection substance, the following are suitable: a substance having an electron-transporting ability and an excellent electron-injecting effect to the light-emitting layer or the light-emitting material, and having an excellent thin film-forming ability.
As specific examples of the electron-injecting substance, liF, naCl, csF, li 2 O, baO, fluorenone, anthraquinone-dimethane, diphenoquinone, thiopyran dioxide,Azole,/>The diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Organic light emitting device
The structure of the organic light emitting device according to the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60. In the above-described structure, the first compound may be included in the hole transport region 30, and the second compound may be included in the light emitting layer 40.
Fig. 2 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole-transporting region 30, a light-emitting layer 40, an electron-transporting region 50, and a cathode 60, wherein the hole-transporting region 30 includes a hole-injecting layer 31, a hole-transporting layer 33, and an electron-blocking layer 35 laminated in this order from the anode 20, and the electron-transporting region 50 includes a hole-blocking layer 51, an electron-transporting layer 53, and an electron-injecting layer 55 laminated in this order from the light-emitting layer 40. In the above-described structure, the first compound may be contained in the hole transport layer 33 or the electron blocking layer 35, and the second compound may be contained in the light emitting layer 40.
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: the anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition: physical vapor deposition) such as sputtering or electron beam evaporation (e-beam evaporation), and the above layers are formed on the anode, and then a substance which can be used as a cathode is deposited on the 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. In addition, the host and the dopant may be formed into the light-emitting layer 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 may 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.
The fabrication of the above-described organic light emitting device is specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Production example 1: production of Compound 1-1
After the compound N, N-bis (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (9.50 g,19.96 mmol) and phenanthrene-9-ylboronic acid (9.30 g,41.91 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.69 g,0.60 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 250ml of ethyl acetate, whereby compound 1-1 (8.46 g, 63%) was produced.
MS[M+H]+＝674
Production example 2: production of Compounds 1-2
After the compound 4 '-bromo-N- (4-bromophenyl) -N-phenyl- [1,1' -biphenyl ] -4-amine (10.50 g,22.06 mmol), phenanthrene-9-ylboronic acid (10.28 g,46.32 mmol) was completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.76 g,0.66 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 220ml of ethyl acetate, whereby compound 1-2 (8.95 g, 60%) was produced.
MS[M+H]+＝674
Production example 3: production of Compounds 1-3
After the compound N- (3-bromophenyl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (10.50 g,22.06 mmol), phenanthrene-9-ylboronic acid (10.28 g,46.32 mmol) was completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.76 g,0.66 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 210ml of ethyl acetate, whereby compounds 1 to 3 (9.24 g, 62%) were produced.
MS[M+H]+＝674
Production example 4: production of Compound 2-1
After the compound 2-bromo-10- (naphthalen-1-yl) -9-phenylanthracene (15.50 g,33.84 mmol) and naphthalen-2-ylboronic acid (6.40 g,37.23 mmol) were completely dissolved in 260ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (130 ml) was added and tetrakis (triphenylphosphine) palladium (1.17 g,1.02 mmol) was added and heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 250ml of ethyl acetate, whereby compound 2-1 (8.64 g, 50%) was produced.
MS[M+H]+＝507
Production example 5: production of Compound 2-2
/>
2M aqueous potassium carbonate (120 ml) was added to the mixture of 2-bromo-10- (naphthalen-9-yl) -9-phenylanthracene (9.50 g,18.70 mmol) and dibenzo [ b, d ] furan-2-ylboronic acid (4.36 g,20.57 mmol) in 240ml of tetrahydrofuran in a 500ml round-bottomed flask under nitrogen atmosphere, and tetrakis (triphenylphosphine) palladium (0.65 g,0.56 mmol) was added thereto and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 240ml of ethyl acetate, whereby compound 2-2 (6.44 g, 58%) was produced.
MS[M+H]+＝597
Production example 6: production of Compounds 2-3
The compound 3- (3-bromo-10-phenylanthracen-9-yl) dibenzo [ b, d ] thiophene (7.50 g,14.59 mmol), [1,1' -biphenyl ] -3-ylboronic acid (3.18 g,16.05 mmol) was completely dissolved in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (90 ml) was added, tetrakis (triphenylphosphine) palladium (0.51 g,0.44 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 270ml of ethyl acetate, whereby compound 2-3 (5.11 g, 89%) was produced.
MS[M+H]+＝589
Example 1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. 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. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HI-1 and the following compound HI-2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer.
On the hole injection layer, the following compound HT-1 as a hole transporting substance is preparedVacuum evaporation is performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe compound 1-1 produced in production example 1 was vacuum-evaporated to form an electron blocking layer. /(I)
Then, on the electron blocking layer, the film thickness is set to beThe compound 2-1 (host) produced in production example 4 and the compound BD-1 (dopant) described below were vacuum-evaporated at a weight ratio of 40:1 to form a light-emitting layer.
On the light-emitting layer, the film thickness is set toThe compound HB-1 was subjected to vacuum evaporation to form a hole blocking layer.
Next, on the hole blocking layer, the following compound ET-1 and the following compound LiQ (Lithium Quinolate, 8-hydroxyquinoline lithium) were vacuum-evaporated at a weight ratio of 1:1 to obtain a filmAn electron transport layer is formed by the thickness of (a). On the electron transport layer, lithium fluoride (LiF) is sequentially added as/>To aluminium/>And the electron injection layer and the cathode are formed by vapor deposition.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride sustain of cathode/sec ]Vapor deposition rate per second, aluminum maintenance/>The vapor deposition rate per second was maintained at 2×10 -7～5×10-6 torr in the vacuum during vapor deposition, and an organic light-emitting device was fabricated.
The compounds used in example 1 above are shown below.
Examples 2 to 9 and comparative examples 1 to 10
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that in example 1 above, the compound described in table 1 below was used instead of the host compound 2-1 and the compound 1-1 of the electron blocking layer, respectively. The compounds used in the above examples and comparative examples are shown below.
Experimental example
When a current of 20mA/cm 2 was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the driving voltage, the light emitting efficiency, and the color coordinates were measured at a current density of 20mA/cm 2, and a time (T95) at which the initial luminance was 95% was measured at a current density of 20mA/cm 2. The results are shown in table 1 below. At this time, T95 means a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device of the example in which the compound represented by the above chemical formula 1 was used as an electron blocking layer material and the compound represented by the above chemical formula 2 was used as a host material of the light emitting layer, exhibited excellent characteristics in terms of driving voltage, light emitting efficiency, and lifetime, as compared with the organic light emitting device of the comparative example in which only one of the compounds represented by the above chemical formulas 1 and 2, or neither of them was used.
Specifically, from comparative examples 1 to 3 and 8 to 10, it is understood that the compound represented by the above chemical formula 1 is superior in hole injection property and hole transport property to the light emitting layer as compared with the compound EB-1 in which the positions 1, 2 and 4 of triphenylene group are substituted with phenyl groups and the tertiary amine compound EB-2 in which no 2 phenanthryl groups are substituted, and thus contributes to improvement in efficiency of the device. From comparative examples 4 to 7, comparative example 9 and comparative example 10, it is found that the compound represented by the above chemical formula 2 contributes to the long life characteristics of the device because the compound has excellent material stability as compared with the comparative example compounds BH-1 and BH-2 having no substituent at the 2-position of anthracene.
In addition, it was confirmed that the efficiency and life characteristics of the organic light emitting device according to the embodiment of the present invention, in which the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 were all employed, were simultaneously improved, unlike the organic light emitting devices of comparative examples 9 and 10 in which the efficiency and life characteristics were not simultaneously improved even though EB-2 and BH-2 and EB-1 and BH-1 were combined with each other. In contrast, when considering that the light-emitting efficiency and lifetime characteristics of an organic light-emitting device normally have a Trade-off relationship with each other, it is known that an organic light-emitting device employing a combination between compounds of the present invention exhibits significantly improved device characteristics compared to a comparative example device.
[ Description of the symbols ]
10: Substrate 20: anode
30: Hole transport region 31: hole injection layer
33: Hole transport layer 35: electron blocking layer
40: Light emitting layer 50: electron transport region
51: Hole blocking layer 53: electron transport layer
55: Electron injection layer 60: and a cathode.
Claims (11)
1. An organic light emitting device, comprising:
An anode;
A cathode provided opposite to the anode;
a light-emitting layer provided between the anode and the cathode;
A hole transport region provided between the anode and the light-emitting layer; and
An electron transport region is provided between the light-emitting layer and the cathode,
The hole transport region includes a first compound represented by the following chemical formula 1, and
The light emitting layer includes a second compound represented by the following chemical formula 2:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 is a single bond or any one selected from the following groups:
Wherein the method comprises the steps of
X 1 is O, S, N (C 6-20 aryl), C (C 1-4 alkyl) 2, or C (C 6-20 aryl) 2,
L 2 and L 3 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
Ar 1 is any one selected from the following groups:
R 1 and R 2 are each independently hydrogen; deuterium; halogen; cyano group; a nitro group; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 1-60 haloalkyl; substituted or unsubstituted C 1-60 haloalkoxy; substituted or unsubstituted C 3-60 cycloalkyl; a substituted or unsubstituted C 2-60 alkenyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S, and
A and b are each integers of 0 to 9,
Chemical formula 2
In the chemical formula 2 described above, the chemical formula,
L 4 and L 5 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
Ar 2 and Ar 3 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S, and
R 3 is substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
2. The organic light-emitting device of claim 1, wherein each of L 1 to L 3 is independently a single bond, or any one selected from the following groups:
3. The organic light-emitting device of claim 1, wherein R 1 and R 2 are each independently hydrogen or phenyl.
4. The organic light-emitting device according to claim 1, wherein the first compound is represented by the following chemical formula 1-1:
Chemical formula 1-1
In the chemical formula 1-1 described above,
L 1 to L 3、Ar1、R1 and R 2 are as defined in claim 1.
5. The organic light-emitting device according to claim 1, wherein the first compound is any one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
6. The organic light-emitting device of claim 1, wherein L 4 and L 5 are each independently a single bond or a phenylene group.
7. An organic light emitting device according to claim 1 wherein Ar 2 and Ar 3 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothiophenyl.
8. An organic light-emitting device according to claim 1 wherein R 3 is any one selected from the group consisting of:
Among the groups of the radicals in which the radicals are formed,
Q is hydrogen, C 1-10 alkyl, si (C 1-4 alkyl) 3 or C 6-20 aryl, and
Y 2 is O, S, N (C 6-20 aryl), C (C 1-4 alkyl) 2, or C (C 6-20 aryl) 2.
9. The organic light-emitting device according to claim 1, wherein the second compound is represented by the following chemical formula 2-1 or 2-2:
Chemical formula 2-1
Chemical formula 2-2
In the chemical formulas 2-1 and 2-2,
L 5、Ar3 and R 3 are as defined in claim 1.
10. The organic light-emitting device according to claim 1, wherein the second compound is any one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
11. The organic light-emitting device of claim 1, wherein the hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer,
The electron blocking layer is positioned in contact with the light emitting layer,
The first compound is contained in the hole transport layer or the electron blocking layer.
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