CN111512458B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN111512458B CN111512458B CN201980006391.9A CN201980006391A CN111512458B CN 111512458 B CN111512458 B CN 111512458B CN 201980006391 A CN201980006391 A CN 201980006391A CN 111512458 B CN111512458 B CN 111512458B
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- 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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Abstract
The present application provides an organic light emitting device, including: an anode, a cathode, a light emitting layer between the anode and the cathode, and an electron transporting layer between the cathode and the light emitting layer, the electron transporting layer exhibiting a current density of 0.1mA/cm in a current density-efficiency graph of the organic light emitting device by including a compound represented by chemical formula 1 2 To 10mA/cm 2 Maximum efficiency value (Eff max ) And a minimum efficiency value (Eff min ) The ratio of (2) is 1.5 or less.
Description
Technical Field
Related applicationPlease refer to each other
The present application claims priority based on korean patent application No. 10-2018-0101609 at 28 of 8.2018 and korean patent application No. 10-2019-0103965 at 23 of 8.2019, the entire contents of the disclosures of which are incorporated as part of the present specification.
The present application 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 from an anode to an organic layer, electrons are injected from a cathode to the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons re-transition to a 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.
An organic light emitting device according to the present invention includes:
an anode electrode,
A cathode electrode,
A light-emitting layer between the anode and the cathode, and
an electron transport layer between the cathode and the light emitting layer,
in the current density-efficiency graph of the above organic light emitting device, the current density was 0.1mA/cm 2 To 10mA/cm 2 Maximum efficiency value (Eff max ) And a minimum efficiency value (Eff min ) The following formula 1 is satisfied,
the electron transport layer contains a compound represented by the following chemical formula 1:
[ mathematics 1]
Eff max /Eff min ≤1.5
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 to L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene 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 1 to 3 heteroatoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
a is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the above chemical formula 2 or 3,
w is O, S, CR 9 R 10 Or SiR 11 R 12 ，
T is benzene, naphthalene or phenanthrene ring condensed with adjacent five-membered ring,
R 1 to R 8 Each independently is hydrogen, deuterium, or cyano, or adjacent R 6 And R is 7 Can be combined with each other to form a spiro structure,
R 9 to R 12 Each independently is hydrogen; deuterium; cyano group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising 1 to 3 heteroatoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
a1 is an integer of 0 to 3,
a2 to a6 and a8 are each independently integers of 0 to 4,
a7 is an integer of 0 to 5,
when a1 to a8 are each 2 or more, structures in parentheses of 2 or more are the same or different from each other,
* L represents the same as the above formula 1 3 The position of the connection is determined by the position of the connection,
however, L 1 To L 3 、Ar 1 、Ar 2 And at least one of A is substituted with cyano. Effects of the invention
The organic light emitting device described above uses the compound represented by chemical formula 1 described later as a material of the electron transport layer, has small change in efficiency due to change in current density, and has small change in color sense due to driving environment, and thus can significantly reduce the defective rate of a panel to which it is applied. In addition, the above organic light emitting device may exhibit characteristics of low voltage, high efficiency, and long life.
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, an electron transport 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, an electron transport layer 4, an electron injection layer 8, and a cathode 5.
Fig. 3 is a graph showing a comparison of efficiency charts of current densities of the organic light emitting devices according to example 16 and comparative example 7.
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,refers to a bond to other substituent groups, and a single bond refers to a bond formed by L 1 To L 3 The indicated portion is free of other atoms.
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 [ ]Alkylthio) is described; arylthio (/ -> Aryl thio xy); alkylsulfonyl [ ]Alkylsulfoxy); arylsulfonyl (+)>Aryl sulfoxy); 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 1 or more substituents in heteroaryl groups containing N, O and 1 or more of S atoms, or 2 of the above exemplified substituentsThe substituent groups formed by connecting the above substituent groups are substituted or unsubstituted. 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 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 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, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, 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. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the 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 heteroatom, 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, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl A group, 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 heteroaryl 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 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 thereto. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and in addition, the above description of heteroaryl groups can be applied.
On the other hand, the organic light emitting device according to the present invention has a current density (mA/cm) in the x-axis 2 ) And the y-axis is the current density-efficiency graph of the efficiency (cd/A) representing the change in efficiency based on current density, at a current density of 0.1mA/cm 2 To 10mA/cm 2 Of the efficiency values measured in the range, the maximum efficiency value (Eff max ) And a minimum efficiency value (Eff min ) The ratio of (2) is 1.5 or less.
In the organic light emitting device satisfying the above equation 1, even if the current density is increased, the efficiency is relatively constant, and the color change based on the driving environment is small, whereby the panel defect rate can be significantly reduced. In contrast, in the organic light emitting device which does not satisfy the above range, the efficiency change based on the current density change is large, and thus, a panel failure may occur. Further, since the change in efficiency based on the change in current density is small, the above-described organic light emitting device can also exhibit characteristics of low driving voltage, high efficiency, and long life.
Such an organic light emitting device satisfying the above formula 1 can be realized by using a compound having a specific structure substituted with one or more cyano groups as a material of an electron transport layer of the above organic light emitting device, and will be described in detail below.
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); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but 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; or LiO 2 And/or Al, but is not limited thereto.
In addition, a hole injection layer may be further included 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: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect on 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.
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 hole-transporting layer used in the present invention is a layer that receives holes from the anode or a hole-injecting layer formed on the anode and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer is suitable, and a substance having a large mobility to the holes 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 light-emitting substance included in the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The main material is aromatic condensed ring derivative, heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
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 one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 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.
Electron transport layer
The organic light emitting device according to the present invention may include an electron transport layer between the above-described light emitting layer and the electron injection layer. The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons.
In particular, in the present invention, a compound represented by the following chemical formula 1 is used as a material of the electron transport layer:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 to L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene 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 1 to 3 heteroatoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
a is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the above chemical formula 2 or 3,
w is O, S, CR 9 R 10 Or SiR 11 R 12 ，
T is benzene, naphthalene or phenanthrene ring condensed with adjacent five-membered ring,
R 1 to R 8 Each independently is hydrogen, deuterium, or cyano, or adjacent R 6 And R is 7 Can be combined with each other to form a spiro structure,
R 9 to R 12 Each independently is hydrogen; deuterium; cyano group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising 1 to 3 heteroatoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
a1 is an integer of 0 to 3,
a2 to a6 and a8 are each independently integers of 0 to 4,
a7 is an integer of 0 to 5,
when a1 to a8 are each 2 or more, structures in parentheses of 2 or more are the same or different from each other,
* L represents the same as the above formula 1 3 The position of the connection is determined by the position of the connection,
however, L 1 To L 3 、Ar 1 、Ar 2 And at least one of A is substituted with cyano.
At this time, "L" of the above chemical formula 1 1 To L 3 、Ar 1 、Ar 2 And at least one of A is substituted by cyano means L 1 Substituent of (L) 2 Substituent of (L) 3 Substituent of (1), ar 1 Substituent of (1), ar 2 Substituent of (a), substituent of a (R 1 To R 12 ) At least one of which is cyano. At this time, L 1 To L 3 By cyano is meant L 1 To L 3 Is C 6-60 Arylene radicals.
By including such a compound having a cyano group represented by the above chemical formula 1 in the electron transport layer, an organic light emitting device satisfying the above chemical formula 1 can be realized.
Specifically, L of the above chemical formula 1 1 Substituent of (L) 2 Substituent of (L) 3 Substituent of (1), ar 1 Substituent of (1), ar 2 Substituent of (a), substituent of a (R 1 To R 12 ) From 1 to 3 of which may be cyano groups.
Preferably L 1 To L 3 、Ar 1 、Ar 2 And one of A is substituted with cyano. In other words, L of the above chemical formula 1 1 Substituent of (L) 2 Substituent of (L) 3 Substituent of (1), ar 1 Substituent of (1), ar 2 Substituent of (a), substituent of a (R 1 To R 12 ) May be cyano groups for 1 or 2 of them.
In the present specification, the term "substituted with cyano" in the definition of a substituent means that 1 or more hydrogen, preferably 1 or 2 hydrogen, among the hydrogens contained in the substituent are substituted with cyano.
The compound represented by the above chemical formula 1 may be represented by the following chemical formula 1A, 1B or 1C:
[ chemical formula 1A ]
In the above-mentioned chemical formula 1A,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
w is O or S, and the R is H,
R 1 to R 4 Each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene groups; or alternatively
Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or alternatively
R 1 To R 4 At least one of which is a cyano group,
[ chemical formula 1B ]
In the above-mentioned chemical formula 1B,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
t is benzene, naphthalene or phenanthrene ring condensed with adjacent five-membered ring,
R 5 to R 8 Each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene radicalsA base; or alternatively
Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or alternatively
R 1 To R 4 At least one of which is a cyano group,
[ chemical formula 1C ]
In the above-mentioned chemical formula 1C,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
R 5 to R 8 、R 6 ' and R 7 ' each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene groups; or alternatively
Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or alternatively
R 5 To R 8 、R 6 ' and R 7 At least one of' is cyano.
In addition, in the present specification, in the definition of a substituent, "C which is unsubstituted or substituted with methyl or cyano 6-20 The term "aryl" refers to unsubstituted C 6-20 Aryl, C substituted by more than 1 methyl group 6-20 Aryl, C substituted by more than 1 cyano group 6-20 Aryl, or C substituted by more than 1 cyano group and more than 1 methyl group 6-20 Aryl groups.
In addition, L 1 To L 3 May each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene groupA base.
For example, L 1 To L 3 Each independently may be a single bond, a phenylene group which is unsubstituted or substituted with a cyano group, or a biphenylene group which is unsubstituted or substituted with a cyano group.
Specifically, for example, L 1 To L 3 Each independently may be a single bond, a phenylene group which is unsubstituted or substituted with a cyano group, a biphenylene group which is unsubstituted or substituted with a cyano group, or a terphenylene group which is unsubstituted or substituted with a cyano group.
In addition, ar 1 And Ar is a group 2 May each independently be C which is unsubstituted or substituted by methyl or cyano 6-20 Aryl groups.
For example, ar 1 And Ar is a group 2 Each independently may be phenyl unsubstituted or substituted with cyano, biphenyl unsubstituted or substituted with cyano, or terphenyl unsubstituted or substituted with cyano, or 9, 9-dimethylfluorene unsubstituted or substituted with cyano.
Specifically, for example, ar 1 And Ar is a group 2 Each independently is phenyl unsubstituted or substituted with 1 or 2 cyano groups, biphenyl unsubstituted or substituted with 1 or 2 cyano groups, or terphenyl unsubstituted or substituted with 1 or 2 cyano groups, or 9, 9-dimethylfluorene unsubstituted or substituted with 1 or 2 cyano groups.
In the chemical formula 2, W may be O or S.
In the above chemical formula 2 or 3, R 1 To R 8 May each independently be hydrogen or cyano. In addition, R 9 To R 12 May each independently be hydrogen; deuterium; cyano group; c unsubstituted or substituted by cyano 6-20 An aryl group; or C containing 1 to 3 hetero atoms selected from N, O and S, which is unsubstituted or substituted by cyano 2-60 Heteroaryl groups. For example, R 9 To R 12 May each independently be hydrogen or cyano.
At this time, a1 to a8 each represent R 1 To R 8 When the number of a1 to a8 is 2 or more, 2 or more R 1 To R 8 May be the same or different from each other. For example, a1 to a8 may each independently be 0 or 1.
In addition, a represented by the above chemical formula 3 may be represented by the following chemical formulas 3-1 to 3-10 according to T. In the case where T is a benzene ring, it can be represented by the following chemical formula 3-1; in the case where T is a naphthalene ring, it can be represented by the following chemical formulas 3-2 to 3-4; in the case where T is a phenanthrene ring, it can be represented by the following chemical formulas 3-5 to 3-10.
In the above chemical formulas 3-1 to 3-10, R 5 To R 8 And a5 to a8 are as defined in formula 3 above, and represents L as defined in formula 1 above 3 The location of the connection.
In addition, R is adjacent to 6 And R is 7 In the case of forming a spiro structure by bonding with each other, a represented by the above chemical formula 3 may have a structure in which one carbon atom is a junction with other compound structures. Specifically, adjacent R of the above chemical formula 3 6 And R is 7 Can be combined with each other to form a spiro structure connected with the fluorene structure by using one carbon atom as a junction, which can be represented by the following chemical formulas 3-11.
In the above chemical formulas 3 to 11, R 5 To R 8 And a5 to a8 are as defined in the above chemical formula 3, R 6 '、R 7 Reference is made to pair R ' respectively to', a6' and a7 6 、R 7 Description of a6 and a7, represents L as defined in formula 1 above 3 The location of the connection.
Specifically, a may be any one selected from the following chemical formulas 4a to 4 e:
in the above chemical formulas 4a to 4e,
w is O or S, and the R is H,
R 1 to R 8 As defined in the above chemical formulas 2 and 3,
R 6 ' and R 7 Reference pair R respectively 6 And R is 7 In the description of (a),
* L represents the same as the above formula 1 3 The location of the connection.
More specifically, in the above chemical formulas 4a to 4e, R 1 To R 8 、R 6 ' and R 7 ' may each independently be hydrogen or cyano.
For example, in the above chemical formula 4a, R 1 To R 4 Is hydrogen or R 1 To R 4 One of which is cyano, the remainder being hydrogen,
in the above chemical formulas 4b to 4d, R 5 To R 8 Is hydrogen or R 5 To R 8 One of which is cyano, the remainder being hydrogen,
in the above chemical formula 4e, R 5 To R 8 、R 6 ' and R 7 ' may be hydrogen, or R 5 To R 8 、R 6 ' and R 7 One of the' groups may be cyano and the remainder hydrogen.
On the other hand, the compound represented by the above chemical formula 1 may be any one selected from the following chemical formulas 1-1 to 1-9:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
In the above chemical formulas 1-1 to 1-9,
w is O or S, and the R is H,
L 1 to L 3 、Ar 1 、Ar 2 And R is 1 To R 8 R is as defined in the above chemical formulas 1 to 3 6 ' and R 7 Reference pair R respectively 6 And R is 7 Is described in (2).
Specifically, the compound represented by the above chemical formula 1 may be any one selected from the following structures:
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on the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1.
[ reaction type 1]
In the above reaction scheme 1, the reaction scheme is as follows 1 To L 3 、Ar 1 、Ar 2 And A is as defined in chemical formula 1 above, X is halogen, preferably bromine or chlorine. The reaction is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst, and the reactive groups for the suzuki coupling reaction may be modified as known in the art. The above-described production method can be more specifically described in the production example described later.
The electron-transporting layer may further contain a known substance as a usual electron-transporting substance, and as a specific example thereof, an Al complex of 8-hydroxyquinoline and Alq may be contained 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, 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, in each case accompanied by an aluminum layer or a silver layer.
Electron injection layer
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound having 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, and an excellent thin film-forming ability. In addition, the electron injection layer may also function as the electron transport layer.
As a specific example of the electron injection material, liF, naCl, csF, li is given 2 O, baO fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, 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.
Organic light emitting device
A structure of an organic light emitting device according to the present invention is illustrated in fig. 1. Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, an electron transport layer 4, and a cathode 5. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron transport layer.
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, an electron transport layer 4, an electron injection layer 8, and a cathode 5. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron transport layer. In this case, the electron transport layer and the electron injection layer may be provided as one layer such as the electron injection and transport layer.
The organic light emitting device according to the present invention may be manufactured by sequentially laminating the above-described structures. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition: physical vapor deposition) methods such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) are used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then the layers are formed on the anode, and then a substance that can be used as a cathode is deposited on the layers. 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 light-emitting layer may be formed using a host and a dopant, and may be formed by a vacuum evaporation method or 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
Compound A1 (10 g,25.2 mmol) and compound B1 (11.6 g,25.2 mmol) were added to tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 1 (13.4 g, yield 82%) was produced.
MS:[M+H] + ＝651
Production example 2: production of Compound 2
Compound A2 (10 g,21.2 mmol) and compound B2 (9.2 g,21.2 mmol) were added to tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100mL)、Pd(dba) 2 (0.5 g), PCy 3 (0.5 g) and stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2 (10.5 g, yield 71%) was produced.
MS:[M+H] + ＝701
Production example 3: production of Compound 3
Compound A3 (10 g,24.3 mmol) and compound B3 (11.2 g,24.3 mmol) were added to tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100mL)、Pd(dba) 2 (0.6 g), PCy 3 (0.6 g) and stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 3 (12.6 g, yield 78%) was produced.
MS:[M+H] + ＝665
Production example 4: production of Compound 4
Compound A4 (10 g,22.9 mmol) and compound B2 (10 g,22.9 mmol) were added to tetrahydrofuran (150 mL). Adding 2M K 2 CO 3 (100mL)、Pd(dba) 2 (0.6 g), PCy 3 (0.6 g) and stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 4 (10.4 g, yield 68%) was produced.
MS:[M+H] + ＝665
Production example 5: production of Compound 5
Compound A5 (10 g,17.9 mmol) and compound B4 (9.6 g,17.9 mmol) were added to tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100mL)、Pd(dba) 2 (0.5 g), PCy 3 (0.5 g) and stirred and refluxed for 5 hours. After cooling to room temperature, filtration was carried out, and the resulting solid was recrystallized from chloroform and ethanol to give the above-mentioned compound 5 (9.9 g, recoveredRate 62%).
MS:[M+H] + ＝890
Production example 6: production of Compound 6
Compound A3 (10 g,24.3 mmol) and compound B5 (11.2 g,24.3 mmol) were added to tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100mL)、Pd(dba) 2 (0.6 g), PCy 3 (0.6 g) and stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 6 (12.9 g, yield 80%) was produced.
MS:[M+H] + ＝665
Production example 7: production of Compound 7
In production example 1, compound 7 was produced in the same manner as in production example 1, except that compound A6 was used instead of compound A1 and compound B6 was used instead of compound B1.
MS:[M+H] + ＝651
Production example 8: production of Compound 8
Compound 8 was produced in the same manner as in production example 1, except that compound B7 was used instead of compound B1 in production example 1.
MS:[M+H] + ＝727
Production example 9: production of Compound 9
In production example 1, compound 9 was produced in the same manner as in production example 1, except that compound A7 was used instead of compound A1 and compound B8 was used instead of compound B1.
MS:[M+H] + ＝777
Production example 10: production of Compound 10
In production example 1, compound 10 was produced in the same manner as in production example 1, except that compound A4 was used instead of compound A1 and compound B9 was used instead of compound B1.
MS:[M+H] + ＝589
Production example 11: production of Compound 11
In production example 1, compound 11 was produced in the same manner as in production example 1, except that compound A3 was used instead of compound A1 and compound B10 was used instead of compound B1.
MS:[M+H] + ＝741
Production example 12: production of Compound 12
In production example 1, compound 12 was produced in the same manner as in production example 1, except that compound A3 was used instead of compound A1 and compound B11 was used instead of compound B1.
MS:[M+H] + ＝893
Production example 13: production of Compound 13
In production example 1, compound 13 was produced in the same manner as in production example 1, except that compound A5 was used instead of compound A1 and compound B9 was used instead of compound B1.
MS:[M+H] + ＝737
Production example 14: production of Compound 14
In production example 1, compound 14 was produced in the same manner as in production example 1, except that compound A8 was used instead of compound A1 and compound B12 was used instead of compound B1.
MS:[M+H] + ＝751
Production example 15: production of Compound 15
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In production example 1, compound 15 was produced in the same manner as in production example 1, except that compound A3 was used instead of compound A1 and compound B13 was used instead of compound B1.
MS:[M+H] + ＝665
Production example 16: production of Compound 16
In production example 1, compound 16 was produced in the same manner as in production example 1, except that compound A3 was used instead of compound A1 and compound B14 was used instead of compound B1.
MS:[M+H] + ＝664
Production example 17: production of Compound 17
In production example 1, compound 17 was produced in the same manner as in production example 1, except that compound A3 was used instead of compound A1 and compound B12 was used instead of compound B1.
MS:[M+H] + ＝665
Example 1
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of fei-hill company (Fischer co.) and the distilled water was filtered twice using a Filter (Filter) manufactured by millbore company (Millipore 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, hexanitrile hexaazabenzophenanthrene (hexanitrile hexaazatriphenylene, HATCN) was used as a substrateAnd performing thermal vacuum evaporation to form a hole injection layer. HT1 +_ as a hole transporting substance on the hole injection layer>Vacuum evaporation is performed to form a hole transport layer.
On the hole transport layer, a host H1 and a dopant D1 are combined to formAnd vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer.
On the light-emitting layer, the compound 1 produced in production example 1 and LiQ (8-hydroxyquinoline lithium, lithi)um Quinolate) was vacuum evaporated at a weight ratio of 1:1An electron transport layer is formed by the thickness of (a).
On the electron transport layer, lithium fluoride (LiF) is sequentially added toIs made of aluminum +.>An electron injection layer and a cathode are formed by vapor deposition, thereby manufacturing an organic light emitting device.
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 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device.
The compounds used in example 1 above are shown below.
Examples 2 to 17 and comparative examples 1 to 10
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 1 below was used as the electron transport layer material in example 1 above instead of compound 1.
The compounds used in the above examples were worked up as follows.
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The compounds used in the above comparative examples were prepared as follows.
Experimental example
The organic light emitting devices manufactured in the above examples and comparative examples were measured at 10mA/cm 2 Drive voltage and luminous efficiency at current density of 20mA/cm 2 The time required for the initial luminance to be 98% (LT 98) is shown in table 1 below.
Further, current density-efficiency charts of the organic light emitting devices manufactured in the above examples and comparative examples were obtained, respectively, and then a current density of 0.1mA/cm was obtained from the charts 2 To 10mA/cm 2 Minimum efficiency value (Eff min ) And a maximum efficiency value (Eff max ) After that, calculate Eff max /Eff min The values and the results are shown in Table 1 below. Further, current density-efficiency charts of the organic light emitting devices of example 16 and comparative example 7 were compared and are shown in fig. 3.
[ Table 1 ]
As shown in the above table 1 and fig. 3, it is known that an organic light emitting device using a compound represented by the above chemical formula 1 as a substance of an electron transport layer is different from that of a comparative example, eff max /Eff min The value of (2) is 1.5 or less. Further, it was confirmed that the organic light-emitting device using the compound represented by the above chemical formula 1 as the electron transport layer was capable of emitting light at a driving voltage as compared with the organic light-emitting device of the comparative exampleBoth in terms of efficiency and lifetime, exhibit excellent characteristics.
This is determined to be because the organic light emitting device using the compound represented by the above chemical formula 1 as an electron transporting layer substance has a small change in efficiency even if the current density is increased as compared with the organic light emitting device of the comparative example, and a small change in color sensation due to the driving environment, thereby improving the driving voltage, efficiency and lifetime. Therefore, when considering the point that the light emission efficiency and lifetime characteristics of the organic light emitting device generally have such a Trade-off relationship with each other, it is known that the organic light emitting device employing the compound of the present invention exhibits significantly improved device characteristics as compared with the device of the comparative example.
[ symbolic description ]
1: substrate 2: anode
3: light emitting layer 4: electron transport layer
5: cathode 6: hole injection layer
7: hole transport layer 8: an electron injection layer.
Claims (9)
1. An organic light emitting device, comprising:
an anode electrode,
A cathode electrode,
A light-emitting layer between the anode and the cathode, and
an electron transport layer between the cathode and the light emitting layer,
in the current density-efficiency graph of the organic light emitting device, the current density was 0.1mA/cm 2 To 10mA/cm 2 Maximum efficiency value Eff max And a minimum efficiency value Eff min The following formula 1 is satisfied,
the electron transport layer includes a compound represented by the following chemical formula 1:
mathematics 1
Eff max /Eff min ≤1.5
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 to L 3 Each independently is a single bond, or C which is unsubstituted or substituted by cyano 6-20 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
a is represented by the following chemical formula 2 or 3,
chemical formula 2
Chemical formula 3
In the chemical formula 2 or 3 described above,
w is O, S, CR 9 R 10 Or SiR 11 R 12 ，
T is benzene, naphthalene or phenanthrene ring condensed with adjacent five-membered ring,
R 1 to R 8 Each independently is hydrogen, deuterium, or cyano, or adjacent R 6 And R is 7 Are combined with each other to form a spiro structure,
R 9 to R 12 Each independently of the other is hydrogen or deuterium,
a1 is an integer of 0 to 3,
a2 to a6 and a8 are each independently integers of 0 to 4,
a7 is an integer of 0 to 5,
when a1 to a8 are 2 or more, R 1 To R 8 More than 2 of the structures are the same or different from each other,
* L represents the same as the formula 1 3 The position of the connection is determined by the position of the connection,
however, L 1 To L 3 、Ar 1 、Ar 2 And at least one of A is substituted with cyano.
2. The organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is represented by the following chemical formula 1A, 1B, or 1C:
chemical formula 1A
In the chemical formula 1A described above, a compound,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 Arylene group, ar 1 And Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 Aryl, W is O or S,
R 1 to R 4 Each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene groups; or Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or R is 1 To R 4 At least one of which is a cyano group,
chemical formula 1B
In the chemical formula 1B described above, a compound having the formula,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 Arylene group, ar 1 And Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
t is benzene, naphthalene or phenanthrene ring condensed with adjacent five-membered ring,
R 5 to R 8 Each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene groups; or alternatively
Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or alternatively
R 1 To R 4 At least one of which is a cyano group,
chemical formula 1C
In the chemical formula 1C described above, a compound having the formula,
L 1 to L 3 Each independently is a single bond; or C which is unsubstituted or substituted by cyano 6-20 An arylene group,
Ar 1 and Ar is a group 2 Each independently is C which is unsubstituted or substituted by methyl or cyano 6-20 An aryl group,
R 5 to R 8 、R 6 ' and R 7 ' each independently hydrogen, deuterium, or cyano,
however, L 1 To L 3 At least one of which is C substituted by cyano 6-20 Arylene groups; or alternatively
Ar 1 And Ar is a group 2 At least one of which is C substituted by cyano 6-20 An aryl group; or alternatively
R 5 To R 8 、R 6 ' and R 7 At least one of' is cyano.
3. The organic light-emitting device of claim 1, wherein L 1 To L 3 Each independently is a single bond, unsubstituted or cyano-substituted phenylene, unsubstituted or cyano-substituted biphenylene, or unsubstituted or cyano-substituted terphenylene.
4. The organic light-emitting device of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl unsubstituted or substituted with cyano, biphenyl unsubstituted or substituted with cyano, terphenyl unsubstituted or substituted with cyano, or 9, 9-dimethylfluorene unsubstituted or substituted with cyano.
5. The organic light-emitting device according to claim 1, wherein a is any one selected from the following chemical formulas 4a to 4 e:
in the chemical formulas 4a to 4e,
w is O or S, and the R is H,
R 1 to R 8 As defined in claim 1,
R 6 ' and R 7 ' each independently hydrogen, deuterium, or cyano,
* L represents the same as the formula 1 3 The location of the connection.
6. The organic light-emitting device of claim 5, wherein R 1 To R 8 、R 6 ' and R 7 ' each independently is hydrogen or cyano.
7. The organic light-emitting device according to claim 5, wherein,
in the chemical formula 4a described above, a compound,
R 1 to R 4 Is hydrogen or R 1 To R 4 One of which is cyano, the remainder being hydrogen,
in the chemical formulas 4b to 4d,
R 5 to R 8 Is hydrogen or R 5 To R 8 One of which is cyano, the remainder being hydrogen,
in the chemical formula 4e described above, the chemical formula,
R 5 to R 8 、R 6 ' and R 7 ' is hydrogen, or R 5 To R 8 、R 6 ' and R 7 One of the' groups is cyano and the remainder are hydrogen.
8. The organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following chemical formulas 1-1 to 1-9:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
Chemical formulas 1-5
Chemical formulas 1-6
Chemical formulas 1-7
Chemical formulas 1-8
Chemical formulas 1-9
In the chemical formulas 1-1 to 1-9,
w is O or S, and the R is H,
L 1 to L 3 、Ar 1 、Ar 2 And R is 1 To R 8 As defined in claim 1,
R 6 ' and R 7 ' each independently is hydrogen, deuterium, or cyano.
9. The organic light-emitting device according to claim 1, wherein the compound is any one selected from the following structures:
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| CN105980520A (en) * | 2014-08-20 | 2016-09-28 | 株式会社Lg化学 | Organic light-emitting device |
| KR20170071399A (en) * | 2015-12-15 | 2017-06-23 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108063188A (en) * | 2016-11-08 | 2018-05-22 | 株式会社Lg化学 | Organic illuminating element |
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| CN105576137A (en) * | 2014-10-31 | 2016-05-11 | 三星Sdi株式会社 | Organic optoelectric device and display device |
| KR20170071399A (en) * | 2015-12-15 | 2017-06-23 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108063188A (en) * | 2016-11-08 | 2018-05-22 | 株式会社Lg化学 | Organic illuminating element |
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