CN116057039B - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- CN116057039B CN116057039B CN202180061919.XA CN202180061919A CN116057039B CN 116057039 B CN116057039 B CN 116057039B CN 202180061919 A CN202180061919 A CN 202180061919A CN 116057039 B CN116057039 B CN 116057039B
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 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
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 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
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 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
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000004882 thiopyrans Chemical class 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
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- 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
- 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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- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/181—Electron blocking layers
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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application claims priority from korean patent application No. 10-2020-0132923, filed to the korean patent office on 14 th 10 months in 2020, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
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 generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. 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.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Prior art literature
(Patent document 1) KR 10-2008-0118112A
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
R1 to R4 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
L1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted hydrocarbon ring group,
Ar11 and Ar12 are the same as or different from each other, each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
Ra is hydrogen, deuterium, alkyl or aryl, or combines with adjacent groups to form a ring substituted or unsubstituted by deuterium, alkyl or aryl,
A to c are each integers of 0 to 3, and when a to c are each 2 or more, 2 or more L1 to L3 are each the same or different from each other,
P is an integer of 0 to 7, and when p is 2 or more, 2 or more Ra are the same or different from each other.
In addition, an embodiment of the present specification provides an organic light emitting device, including: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compounds described in this specification can be used as materials for organic layers of organic light-emitting devices. According to the compound of at least one embodiment of the present specification, an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics can be achieved in an organic light emitting device. In particular, the compounds described in this specification can be used as a hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material. In addition, it has effects of lower driving voltage, high efficiency and/or long life compared to the existing organic light emitting device.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are stacked in this order.
Fig. 2 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron suppression layer 5, a light-emitting layer 6, a hole suppression layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order.
Description of symbols
1: Substrate board
2: Anode
3: Hole injection layer
4: Hole transport layer
5: Electron suppression layer
6: Light-emitting layer
7: Hole-inhibiting layer
8: Electron injection and transport layers
9: And a cathode.
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present description of the invention,Represents the site of binding to a chemical formula or compound.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with a member selected from deuterium, halogen group, nitrile group (-CN), nitro, hydroxy, alkyl, cycloalkyl, alkoxy, phosphine oxide group, aryloxy, alkylthio groupArylthioAlkylsulfonylArylsulfonyl1 Or 2 or more substituents selected from the group consisting of alkenyl, silyl, boron, amino, aryl and heterocyclic groups are substituted, or a substituent obtained by linking 2 or more substituents selected from the above-exemplified substituents is substituted, or no substituent is present. 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 term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents selected from the above-exemplified substituents are linked, or does not have any substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen groups, nitrile groups, alkyl groups, aryl groups, and heterocyclic groups, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by the chemical formula of-SiY aYbYc, and each of the above Y a、Yb and Y c may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but 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 may be represented BY the chemical formula of-BY dYe, and each of the above Y d and Y e may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include, but are not limited to, dimethylboronyl, diethylboronyl, t-butylmethylboronyl, diphenylboronyl, and the like.
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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 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, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.
In this specification, the above description of the alkyl group may be applied to the arylalkyl group other than the aryl group.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy and the like are possible, but not limited thereto.
The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described in this specification are all included in straight or branched chain forms.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the alkynyl group is a substituent group including a triple bond between carbon atoms, and may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the above alkynyl group has 2 to 10 carbon atoms.
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, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the amine group is-NH 2, and the above alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, and the like may be substituted on the above amine group. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the amine group has 1 to 20 carbon atoms. According to one embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, 9-dimethylfluorenylphenylamino group, pyridylphenylamino group, diphenylamino group, phenylpyridylamino group, naphthylamino group, biphenylamino group, anthracenyl amino group, dibenzofuranylphenylamino group, 9-methylanthrenylamino group, phenylnaphthylamino group, xylylamino group, phenyltolylamino group and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, a triphenylene group, and the like, 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 this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
In the case where the above fluorenyl group is substituted, it may beAn isospirofluorenyl group; /(I)(9, 9-Dimethylfluorenyl) and(9, 9-Diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the aryl group in the aryloxy group may be applied to the above description about the aryl group.
In the present specification, the above-mentioned alkyl groups in the alkylthio group and the alkylsulfonyl group may be applied to the above-mentioned explanation about the alkyl group.
In the present specification, the above-described aryl groups in the arylthio group and the arylsulfonyl group can be applied to the above-described description about the aryl group.
In the present specification, the heterocyclic group is a ring group containing 1 or more hetero atoms of N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarzolyl, triazinyl, and the like.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
In this specification, the above description of the aryl group may be applied in addition to the arylene group having a valence of 2.
In this specification, the above description of the heterocyclic group may be applied in addition to the heterocyclic ring having 2 valences.
In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The aromatic hydrocarbon ring group may be as described above with respect to the aryl group, and the aliphatic hydrocarbon ring group may be as described above with respect to the cycloalkyl group.
In the present specification, the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may include a structure in which an aliphatic hydrocarbon ring is condensed on an aryl group. According to one embodiment, the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may include a substituted or unsubstituted tetrahydronaphthyl group. In this case, the tetrahydronaphthyl group may be, for exampleAs an example of the substituted or unsubstituted tetrahydronaphthyl group, it is shown that/>, may be contained(1, 4-Tetramethyl-1, 2,3, 4-tetrahydronaphthyl), but is not limited thereto.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups.
In this specification, the meaning of a ring formed by bonding adjacent groups to each other is that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof is formed by bonding adjacent groups to each other. The hydrocarbon ring refers to a ring composed of only carbon and hydrogen atoms. The heterocyclic ring is a ring containing 1 or more elements selected from N, O, P, S, si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be monocyclic or polycyclic.
In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like.
In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, and,Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-Alkane (1, 4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxepane AzacyclooctaneThiacyclooctaneAnd the like, but is not limited thereto.
In the present specification, an aromatic heterocycle means an aromatic ring containing 1 or more hetero atoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,Oxazole, isoOxazole, thiazole, isothiazole, triazole,Diazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, pyridazines,Oxazine, thiazine, twoAlkene, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzoOxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoOxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.
Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.
The compound represented by the chemical formula 1 of the present invention is an amine compound containing tetrahydronaphthalene, and the HOMO and LUMO energy levels of the compound are adjusted by changing the binding position of the fluorenyl group to the amine group, whereby the energy level barrier with the organic layer can be adjusted. Further, by containing a tetrahydronaphthyl group, high heat resistance is exhibited as compared with the molecular weight, and characteristics of high efficiency and long life are exhibited.
Accordingly, when the compound represented by the above chemical formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.
Chemical formula 1 will be described in detail below.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
R1 to R4 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
L1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted hydrocarbon ring group,
Ar11 and Ar12 are the same as or different from each other, each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
Ra is hydrogen, deuterium, alkyl or aryl, or combines with adjacent groups to form a ring substituted or unsubstituted by deuterium, alkyl or aryl,
A to c are each integers of 0 to 3, and when a to c are each 2 or more, 2 or more L1 to L3 are each the same or different from each other,
P is an integer of 0 to 7, and when p is 2 or more, 2 or more Ra are the same or different from each other.
In one embodiment of the present specification, R1 to R4 are the same or different from each other and each independently is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R1 to R4 are the same or different and each is independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms.
In one embodiment of the present specification, R1 to R4 are the same or different and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
In one embodiment of the present specification, R1 to R4 are the same or different and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
In one embodiment of the present specification, R1 to R4 are the same or different and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
In one embodiment of the present specification, R1 to R4 are the same or different from each other, and each is independently a substituted or unsubstituted methyl group.
In one embodiment of the present specification, R1 to R4 are methyl groups.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group.
In one embodiment of the present specification, L1 is a direct bond.
In one embodiment of the present specification, the L2 is a direct bond.
In one embodiment of the present specification, the L3 is a direct bond.
In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group.
In one embodiment of the present specification, the L2 is a substituted or unsubstituted arylene group.
In one embodiment of the present specification, the above L3 is a substituted or unsubstituted arylene group.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a directly bonded or substituted or unsubstituted monocyclic to tricyclic arylene group.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently an arylene group directly bonded or substituted or unsubstituted with an alkyl group or an aryl group.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently an arylene group having 6 to 30 carbon atoms, which is directly bonded to or substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently an arylene group which is directly bonded or substituted or unsubstituted with an alkyl group.
In an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group.
In an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, an alkyl-or aryl-substituted or unsubstituted phenylene group, an alkyl-or aryl-substituted or unsubstituted biphenylene group, an alkyl-or aryl-substituted or unsubstituted naphthylene group, or an alkyl-or aryl-substituted or unsubstituted fluorenylene group.
In an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, or a fluorenylene group substituted or unsubstituted with an alkyl group or an aryl group.
In an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, or a fluorenylene group substituted or unsubstituted with a methyl group or a phenyl group.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, or a fluorenylene group substituted or unsubstituted with a methyl group.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, phenylene, biphenylene, naphthylene, or dimethylfluorenylene.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, or an arylene group.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently an arylene group having 6 to 30 carbon atoms or a direct bond.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, phenylene, biphenylene or naphthylene.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond or a phenylene group.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond or represented by any one of the following structures. .
In the above structure, the broken line indicates the bonding position.
In one embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond or represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
In one embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, phenylene, biphenylene, or naphthylene.
In one embodiment of the present specification, L1 is a direct bond, phenylene, biphenylene, or naphthylene.
In one embodiment of the present specification, L1 is a direct bond or phenylene group.
In one embodiment of the present specification, the L2 is a direct bond or a phenylene group.
In one embodiment of the present specification, the L3 is a direct bond, phenylene or biphenylene.
In one embodiment of the present specification, the L3 is a direct bond or a phenylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently a direct bond or represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
In one embodiment of the present specification, L3 is a direct bond or represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted hydrocarbon ring group.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to tetracyclic hydrocarbon ring group.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to tricyclic hydrocarbon ring group.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted hydrocarbon ring group having 6 to 60 carbon atoms.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted aryl group, or a condensed ring group of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a monocyclic to tetracyclic ring group in which a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring are condensed.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to tricyclic aryl group, or a substituted or unsubstituted monocyclic to tricyclic condensed ring group in which an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring are condensed.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to tricyclic aryl group, or a bicyclic condensed ring group in which a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring are condensed.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic to bicyclic aryl group, or a bicyclic condensed ring group in which a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring are condensed.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a condensed ring group of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 60 carbon atoms and an aromatic hydrocarbon ring having 6 to 60 carbon atoms.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a condensed ring group of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, or a condensed ring group of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 24 carbon atoms.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a condensed ring group of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar1 is an aryl group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; or a condensed ring group of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring, which are substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group.
In one embodiment of the present specification, ar1 is an aryl group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; or a condensed ring group of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring which are substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar1 is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms; or a condensed ring group of an aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms.
In one embodiment of the present specification, ar1 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; or a condensed ring group of an aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
In one embodiment of the present specification, ar1 is an aryl group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; or a benzene ring group fused with a cycloalkane substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar1 is an aryl group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; or a benzene ring group fused with cyclohexane substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar1 is an aryl group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; or tetrahydronaphthyl substituted or unsubstituted with alkyl.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetralphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted tetrahydronaphthyl group.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted tetrahydronaphthyl group.
In one embodiment of the present specification, ar1 is phenyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; biphenyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; terphenyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; naphthyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; fluorenyl substituted or unsubstituted with methyl or phenyl; or tetrahydronaphthyl substituted or unsubstituted with methyl.
In one embodiment of the present specification, ar1 is phenyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; a biphenyl group; a terphenyl group; a naphthyl group; a dimethylfluorenyl group; phenyl fluorenyl; diphenyl fluorenyl; or tetrahydronaphthyl substituted with methyl.
In one embodiment of the present specification, ar1 is phenyl substituted or unsubstituted with tert-butyl, adamantyl, phenyl, biphenyl or naphthyl; a biphenyl group; a terphenyl group; a naphthyl group; a dimethylfluorenyl group; diphenyl fluorenyl; or alternativelyIndicating the binding site.
In one embodiment of the present specification, ar1 is represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position. The above structure is substituted or unsubstituted with methyl, tert-butyl, adamantyl, phenyl, biphenyl or naphthyl.
In one embodiment of the present specification, ar1 is represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
In the above structure, the dotted line represents a bonding position, and the above structure is substituted or unsubstituted with methyl, tert-butyl, adamantyl, phenyl, biphenyl, or naphthyl.
In one embodiment of the present specification, ar1 is phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, or tetrahydronaphthyl substituted with methyl.
In one embodiment of the present specification, ar1 is phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, orIndicating the binding site.
In one embodiment of the present specification, ar11 and Ar12 are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring formed by combining adjacent groups with each other.
In one embodiment of the present specification, ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, ar11 and Ar12 are the same as or different from each other, and each is independently methyl or phenyl.
In one embodiment of the present specification, ra is hydrogen, deuterium, alkyl or aryl, or is bonded to each other with an adjacent group to form a ring substituted or unsubstituted with deuterium, alkyl or aryl.
In one embodiment of the present specification, ra is hydrogen, deuterium, alkyl or aryl, or is bonded to an adjacent group to form an aromatic hydrocarbon ring substituted or unsubstituted with deuterium, alkyl or aryl.
In one embodiment of the present specification, ra is hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, ra is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or is bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, ra is hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, or is bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ra is hydrogen or deuterium, or is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present specification, ra is hydrogen or deuterium, or is bonded to each other with an adjacent group to form a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, ra is hydrogen or deuterium, or is bonded to an adjacent group to form a benzene ring.
In one embodiment of the present specification, ra is hydrogen, or is bonded to an adjacent group to form a benzene ring.
In one embodiment of the present specification, ra is hydrogen or deuterium.
In one embodiment of the present specification, ra is hydrogen.
In an embodiment of the present specification, each of a to c is an integer of 0 to 3.
In an embodiment of the present specification, each of a to c is an integer of 1 to 3.
In an embodiment of the present specification, each of a to c is 3.
In one embodiment of the present specification, each of a to c is 2.
In one embodiment of the present specification, each of a to c is 1.
In one embodiment of the present specification, each of a to c is 0.
In one embodiment of the present specification, p is an integer of 0 to 7.
In one embodiment of the present specification, p is an integer of 1 to 7.
In one embodiment of the present specification, p is 0.
In one embodiment of the present specification, p is 1.
In one embodiment of the present specification, p is 7.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
[ Chemical formula 1-1]
[ Chemical formulas 1-2]
[ Chemical formulas 1-3]
[ Chemical formulas 1-4]
In the above chemical formulas 1-1 to 1-4,
The definitions of R1 to R4, L1 to L3, ar1, ar11, ar12, ra, a to c, and p are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the above chemical formula 1 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,
The definitions of R1 to R4, L1 to L3, ar1, ar11, ar12, ra, a to c, and p are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.
[ Chemical formula 3-1]
[ Chemical formula 3-2]
In the above chemical formulas 3-1 and 3-2,
R1 to R4, L1 to L3, ar11, ar12, ra, a to c and p are as defined in the above chemical formula 1,
R5 to R8 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
One of Ar21, ar22 and Rb is linked to L1,
Ar21 and Ar22 not connected to L1 are the same as or different from each other, each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
Rb which is not attached to L1 is hydrogen, deuterium, alkyl or aryl, or is combined with adjacent groups to each other to form a ring substituted or unsubstituted with deuterium, alkyl or aryl,
Q is an integer of 0 to 7, and when q is 2 or more, 2 or more Rb are the same or different from each other. In one embodiment of the present specification, in the above chemical formula 3-1, Identical to each other.
In one embodiment of the present specification, the above chemical formula 3-1 is represented by the following chemical formula 3-1-1 or 3-1-2.
In the above chemical formulas 3-1-1 and 3-1-2, the definition of the substituents is the same as that in the above chemical formula 3-1.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 4-1 to 4-4 and 5-1 to 5-4.
In the above chemical formulas 4-1 to 4-4 and 5-1 to 5-4,
The definitions of R1 to R4, L1 to L3, ar1, ar11, ar12, and a to c are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.
The compound represented by chemical formula 1 according to an embodiment of the present specification may be manufactured by the same method as the following equations 1-1 and 1-2 or equation 2. The substituents may be bonded by methods known in the art, and the kinds, positions or numbers of the substituents may be changed according to techniques known in the art.
< Reaction No. 1-1>
< Reaction No. 1-2>
< Reaction No. 2>
In the above-mentioned formulas 1-1, 1-2 and 2, the definition of the substituent is the same as that in the above-mentioned formula 1, and X may be a halogen group such as Cl or Br.
The synthesis of a compound having a specific substituent attached to a specific position is exemplified in the above reaction formula 1, but a compound corresponding to the range of the above chemical formula 1 can be synthesized by a synthesis method known in the art using a starting material, an intermediate material, or the like known in the art.
In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in this specification, by introducing various substituents into the core structure of the structure shown above, HOMO and LUMO energy levels of the compound can also be adjusted.
In addition, the present specification provides an organic light emitting device including the above-mentioned compound.
The organic light emitting device according to the present specification is characterized by comprising: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic light emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light emitting device, except that the organic layer is formed by using the compound of chemical formula 1.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more of a hole transporting layer, a hole injecting layer, an electron suppressing layer, a hole transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole suppressing layer, and an electron transporting and injecting layer as the organic layer. The structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present specification, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by chemical formula 1 described above.
In the organic light emitting device of the present specification, the organic layer may include a hole transporting layer or a hole injecting layer, and the hole transporting layer or the hole injecting layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes an electron-inhibiting layer, and the electron-inhibiting layer includes a compound represented by chemical formula 1.
In an embodiment of the present specification, the organic layer may include an electron injection layer, an electron transport and injection layer, or a hole-blocking layer, and the electron injection layer, the electron transport and injection layer, or the hole-blocking layer may include a compound represented by chemical formula 1.
In an embodiment of the present specification, the organic layer includes an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, and the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes an electron modulation layer, and the electron modulation layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a hole-suppressing layer, and the hole-suppressing layer includes a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer is an electron transporting and injecting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the thickness of the organic layer including the compound of formula 1 isToPreferablyToMore preferablyTo
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a main body.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant.
In another embodiment, the organic layer may contain other organic compounds, metals, or metal compounds in addition to the compound represented by the chemical formula 1.
In an organic light emitting device according to an embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer includes 1 to 50 parts by weight with respect to 100 parts by weight of the host.
As another example, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a host, and further includes an additional host.
In one embodiment of the present disclosure, the dopant includes an arylamine compound, a boron or nitrogen-containing heterocyclic compound, an Ir complex, or the like.
The organic light emitting device of the present specification may further include 1 or more organic layers among a hole transporting layer, a hole injecting layer, an electron suppressing layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole suppressing layer, and a hole transporting and injecting layer. In an embodiment of the present specification, the organic layer may further include 1 or more of a hole transporting layer, a hole injecting layer, an electron suppressing layer, a hole transporting and injecting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a hole suppressing layer, and an electron injecting and transporting layer.
In one embodiment of the present specification, the organic light emitting device includes an anode, a cathode, and 2 or more organic layers disposed between the anode and the cathode, wherein at least one of the 2 or more organic layers includes a compound represented by chemical formula 1.
In one embodiment of the present specification, the 2 or more organic layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injecting layer, and an electron-suppressing layer.
In one embodiment of the present specification, the 2 or more organic layers may be two or more selected from the group consisting of a light-emitting layer, an electron transporting layer, an electron injecting layer, an electron transporting and injecting layer, an electron adjusting layer, and a hole suppressing layer.
In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be contained in 1 layer of the 2 or more electron transport layers, and may be contained in each of the 2 or more electron transport layers.
In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.
When the organic layer containing the compound represented by the above chemical formula 1 is an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may further contain an n-type dopant. The n-type dopant may use materials known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate, lithium quinolinate). According to one example, the compound represented by chemical formula 1 above and the n-type dopant above may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
According to one example, the compound represented by chemical formula 1 above and the n-type dopant above may be included in a weight ratio of 1:1.
In one embodiment of the present specification, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the above-described 2 or more hole transport layers, and may be contained in each of the 2 or more hole transport layers.
In addition, in an embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.
In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by the chemical formula 1.
In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light-emitting device may have a reverse structure (inverted type (INVERTED TYPE)) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
In the organic light emitting device of the present invention, the organic layer may include an electron suppression layer, and the electron suppression layer may use materials known in the art.
For example, the above-described organic light emitting device may have a laminated structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 9 are sequentially stacked. In the structure shown above, the above-described compound may be contained in the above-described light-emitting layer 6.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron suppression layer 5, a light emitting layer 6, a hole suppression layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order. In the structure shown above, the above-described compound may be contained in the hole injection layer 3, the hole transport layer 4, the electron suppression layer 5, the light-emitting layer 6, the hole suppression layer 7, or the electron injection and transport layer 8.
In one embodiment of the present disclosure, the electron suppression layer and the light emitting layer may be disposed adjacent to each other. For example, the electron suppression layer and the light-emitting layer may be physically connected to each other.
In one embodiment of the present disclosure, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be physically connected to each other.
The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that 1 or more of the organic layers include the above-described compound, i.e., the compound represented by the above chemical formula 1.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present specification may be manufactured as follows: an 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 (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance usable as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may further include one or more of a hole transporting layer, a hole injecting layer, an electron suppressing layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole suppressing layer, and a hole transporting and injecting layer.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, or the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention 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, indium Zinc Oxide); 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.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance 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.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) 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 (porphyrine), 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. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the movement of holes can be prevented.
In one embodiment of the present specification, the hole injection layer may include one or more kinds of N-containing polycyclic compounds including cyano groups or amine compounds including carbazolyl groups. In this case, the N-containing polycyclic compound may be 1,4,5,8,9,11-hexanitrile hexaazatriphenylene (1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile) (HATCN). According to one example, the hole transport layer may contain the above-described compound alone, or may contain 2 or more kinds.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and 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.
According to an embodiment of the present specification, the hole transport layer may include a compound represented by formula 1 of the present invention.
According to an embodiment of the present disclosure, the hole transport layer may include an arylamine compound including a carbazole group.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron-inhibiting layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-inhibiting layer may be formed using the above-described compound or a material known in the art.
In one embodiment of the present specification, the electron suppression layer may include a compound represented by chemical formula 1 of the present invention.
In one embodiment of the present specification, the electron-inhibiting layer may include an arylamine compound having a carbazole group.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance 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 is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); 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.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a 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.
When the light-emitting layer emits red light, a phosphorescent substance such as PIQIr (acac) ((bis (1-phenylisoquinoline) acetylacetonateiridium, bis (1-phenylisoquinoline) iridium acetylacetonate), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) iridium acetylacetonate), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin) or a fluorescent substance such as Alq 3 (tris (8-hydroxyquinolino) aluminum, tris (8-hydroxyquinoline) aluminum) may be used as the light-emitting dopant, but when the light-emitting layer emits green light, a phosphorescent substance such as Ir (ppy) 3 (factris (2-PHENYLPYRIDINE) iridium, planar tris (2-phenylpyridine) iridium)) or a fluorescent substance such as Alq 3 (tris (8-hydroxyquinoline) aluminum) may be used. When the light-emitting layer emits blue light, a phosphorescent material such as (4, 6-F 2ppy)2 Ir pic) or a fluorescent material such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO polymer or PPV polymer may be used as the light-emitting dopant, but is not limited thereto.
In one embodiment of the present disclosure, the light-emitting layer may contain an anthracene compound substituted with an aryl group or a heterocyclic group as a host, and may contain a pyrene compound substituted with an amine group as a dopant. According to one example, the anthracene compound is a structure in which carbon number 9 and carbon number 10 are substituted with an aryl or heterocyclic group. The host and dopant may be included in a suitable weight ratio, and according to one example, the host and dopant may be included in a weight ratio of 100:1 to 100:10.
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.
In one embodiment of the present specification, the hole blocking layer may include a compound having a heterocyclic group containing N.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specific examples include, but are not limited to, the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for improving the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
In an embodiment of the present specification, the electron injection layer or the electron transport layer may include a compound having 2N-containing heterocyclic groups, and may further include an N-type dopant or an organometallic compound. According to one example, the N-type dopant or organometallic compound may be LiQ, and the compound containing 2N-heterocyclic groups and the N-type dopant (or organometallic compound) may be contained in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
The hole-suppressing layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the hole-injecting layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
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 organic light emitting device according to the present specification may be included in a variety of electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, or the like, but is not limited thereto.
Modes for carrying out the invention
In the following, examples will be given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. Embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example
Synthesis example 1 Synthesis of Compound 1
Step 1) Synthesis of Compound 1-A
Toluene (800 ml) was added to 9, 9-dimethyl-9H-fluoren-2-amine (50.0 g,238.90 mmol), 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (63.84 g,238.90 mmol), and sodium t-butoxide (32.14 g,33.45 mmol), followed by stirring with heating for 10 minutes. To the above mixture was added 1,1' -bis (diphenylphosphine) ferrocene palladium (II) dichloride (0.87 g,1.19 mmol) dissolved in toluene (50 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After the solvent was removed, it was recrystallized from ethyl acetate, whereby the above-mentioned compound 1-A (72.0 g,76.19% yield) was obtained.
Step 2) Synthesis of Compound 1
Toluene (300 ml) was added to the compound 1-A (20.0 g,50.56 mmol), 4-bromo-1, 1' -biphenyl (12.02 g,51.57 mmol) and sodium tert-butoxide (6.80 g,70.78 mmol) obtained in step 1 of synthesis example 1 above, followed by heating and stirring for 10 minutes. To the above mixture was added bis (tri-t-butylphosphine) palladium (0.13 g,0.25 mmol) dissolved in toluene (30 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After the solvent was removed, it was recrystallized from ethyl acetate, whereby the above-mentioned compound 1 (21.0 g,75.82% yield) was obtained. (MS [ m+h ] + =548)
Synthesis example 2 Synthesis of Compound 2
Using the compound 1-A (20.0 g,50.56 mmol) obtained in step 1 of synthesis example 1 and 1- (4-bromophenyl) naphthalene (14.60 g,51.57 mmol), the compound 2 (22.8 g,75.43% yield) was obtained by the same method as step 2 of synthesis example 1. (MS [ m+h ] + =598)
Synthesis example 3 Synthesis of Compound 3
Using the compound 1-A (20.0 g,50.56 mmol) obtained in step 1 of synthesis example 1 and 2- (4-bromophenyl) naphthalene (14.60 g,51.57 mmol), the compound 3 (23.0 g,76.09% yield) was obtained by the same method as step 2 of synthesis example 1. (MS [ m+h ] + =598)
Synthesis example 4 Synthesis of Compound 4
Using the compound 1-A (20.0 g,50.56 mmol) obtained in step 1 of synthesis example 1 and 2-bromo-9, 9-diphenyl-9H-fluorene (20.49 g,51.57 mmol), the compound 4 (28.0 g,77.78% yield) was obtained by the same method as in step 2 of synthesis example 1. (MS [ m+h ] + =712)
Synthesis example 5 Synthesis of Compound 5
Step 1) Synthesis of Compound 5-A
The above compound 5-A (70.0 g,74.07% yield) was obtained by the same method as step 1 of the above synthesis example 1 using 9, 9-dimethyl-9H-fluoren-2-amine (50.0 g,238.90 mmol) and 5-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (63.84 g,238.90 mmol).
Step 2) Synthesis of Compound 5
Using the compound 5-A (20.0 g,50.56 mmol) obtained in step 1 of the above-described synthetic example 5 and 4-bromo-1, 1' -biphenyl (12.02 g,51.57 mmol), the above-described compound 5 (20.5 g,74.02% yield) was obtained by the same method as step2 of the above-described synthetic example 1. (MS [ m+h ] + =548)
Synthesis example 6 Synthesis of Compound 6
Using 5-A (20.0 g,50.56 mmol) and 2-bromo-9, 9-diphenyl-9H-fluorene (20.49 g,51.57 mmol) obtained in step 1 of above-described synthetic example 5, the above-described compound 6 (27.5 g,76.39% yield) was obtained by the same method as in step 2 of above-described synthetic example 1. (MS [ m+h ] + =712)
Synthesis example 7 Synthesis of Compound 7
Step 1) Synthesis of Compound 7-A
Tetrahydrofuran (THF) (400 ml) was added to 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (50.00 g,187.12 mmol) and (4-chlorophenyl) boric acid (30.72 g,196.47 mmol), followed by stirring with heating. To the above solution, an aqueous solution (200 ml) of potassium carbonate (77.59 g,561.36 mmol) was added, followed by stirring with heating for 5 minutes. To the above solution, 1' -bis (diphenylphosphine) ferrocene palladium (II) dichloride (1.10 g,1.50 mmol) was slowly added dropwise, and then heated and stirred for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After the solvent was removed, it was recrystallized from n-hexane, whereby compound 7-a (39.0 g,69.74% yield) was obtained.
Step 2) Synthesis of Compound 7
To 9, 9-dimethyl-9H-fluoren-2-amine (15.0 g,71.67 mmol), the compound 7-A (43.91 g,146.93 mmol) obtained in step 1 of the above-mentioned Synthesis example 7, and sodium t-butoxide (19.28 g,200.61 mmol) were added xylene (300 ml), followed by stirring with heating for 10 minutes. To the above mixture was added bis (tri-t-butylphosphine) palladium (0.29 g,0.57 mmol) dissolved in xylene (30 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with xylene and water. After the solvent was removed, it was recrystallized from ethyl acetate, whereby the above-mentioned compound 7 (39.5 g,75.08% yield) was obtained. (MS [ m+h ] + =734)
Synthesis example 8 Synthesis of Compound 8
Using 9, 9-dimethyl-9H-fluoren-3-amine (15.0 g,71.67 mmol) and the compound 7-A (43.91 g,146.93 mmol) obtained in step 1 of the above-described synthetic example 7, the above-described compound 8 (40.0 g,76.03% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =734)
Synthesis example 9 Synthesis of Compound 9
Using 9, 9-xylene-9H-fluoren-4-amine (15.0 g,71.67 mmol) and the compound 7-A (43.91 g,146.93 mmol) obtained in step 1 of the above-described synthetic example 7, the above-described compound 9 (41.5 g,78.88% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =734)
Synthesis example 10 Synthesis of Compound 10
Step 1) Synthesis of Compound 10-A
Using 5-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (50.00 g,187.12 mmol) and (4-chlorophenyl) boronic acid (30.72 g,196.47 mmol), the above compound 10-A (38.0 g,67.95% yield) was obtained by the same method as in step 1 of the above synthesis example 7.
Step 2) Synthesis of Compound 10
Using 9, 9-dimethyl-9H-fluoren-2-amine (15.0 g,71.67 mmol) and the compound 10-A (43.91 g,146.93 mmol) obtained in step 1 of the above-described synthetic example 10, the above-described compound 10 (39.0 g,74.13% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =734)
Synthesis example 11 Synthesis of Compound 11
Using 9, 9-dimethyl-9H-fluoren-4-amine (15.0 g,71.67 mmol) and the compound 10-A (43.91 g,146.93 mmol) obtained in step 1 of the above-described synthetic example 10, the above-described compound 11 (41.0 g,77.93% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =734)
Synthesis example 12 Synthesis of Compound 12
Step 1) Synthesis of Compound 12-A
Using 9, 9-diphenyl-9H-fluoren-2-amine (50.0 g,149.96 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (40.07 g,149.96 mmol), the above-mentioned compound 12-A (60.0 g,76.98% yield) was obtained by the same method as in step 1 of the above-mentioned synthetic example 1.
Step 2) Synthesis of Compound 12
Using the compound 12-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 12 and 4-bromo-1, 1' -biphenyl (9.15 g,39.25 mmol), the above-described compound 12 (20.5 g,79.29% yield) was obtained by the same method as step 2 of the above-described synthetic example 1. (MS [ m+h ] + =672)
Synthesis example 13 Synthesis of Compound 13
Using the compound 12-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 12 and 1- (4-bromophenyl) naphthalene (11.11 g,39.25 mmol), the above-described compound 13 (21.5 g,77.39% yield) was obtained by the same method as step 2 of the above-described synthetic example 1. (MS [ m+h ] + =722)
Synthesis example 14 Synthesis of Compound 14
Using the compound 12-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 12 and 2- (4-bromophenyl) naphthalene (11.11 g,39.25 mmol), the above-described compound 14 (22.0 g,79.19% yield) was obtained by the same method as step 2 of the above-described synthetic example 1. (MS [ m+h ] + =722)
Synthesis example 15 Synthesis of Compound 15
Using the compound 12-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 12 and 2-bromo-9, 9-diphenyl-9H-fluorene (15.59 g,39.25 mmol), the above-described compound 15 (25.0 g,77.70% yield) was obtained by the same method as in step 2 of the above-described synthetic example 1. (MS [ m+h ] + =836)
Synthesis example 16 Synthesis of Compound 16
Using the compound 12-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 12 and 2- (4-chlorophenyl) -9, 9-dimethyl-9H-fluorene (11.96 g,39.25 mmol), the above-described compound 16 (23.5 g,77.49% yield) was obtained by the same method as in step 2 of the above-described synthetic example 1. (MS [ m+h ] + =788)
Synthesis example 17 Synthesis of Compound 17
Step 1) Synthesis of Compound 17-A
The above-mentioned compound 17-A (58.0 g,74.42% yield) was obtained by the same method as step 1 of the above-mentioned synthetic example 1 using 9, 9-diphenyl-9H-fluoren-2-amine (50.0 g,149.96 mmol) and 5-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (40.07 g,149.96 mmol).
Step 2) Synthesis of Compound 17
Using the compound 17-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 17 and 4-bromo-1, 1' -biphenyl (9.15 g,39.25 mmol), the above-described compound 17 (20.0 g,77.35% yield) was obtained by the same method as step 2 of the above-described synthetic example 1. (MS [ m+h ] + =672)
Synthesis example 18 Synthesis of Compound 18
Using the compound 17-A (20.0 g,38.48 mmol) obtained in step 1 of the above-described synthetic example 17 and 2-bromo-9, 9-diphenyl-9H-fluorene (15.59 g,39.25 mmol), the above-described compound 18 (25.7 g,79.88% yield) was obtained by the same method as in step 2 of the above-described synthetic example 1. (MS [ m+h ] + =836)
Synthesis example 19 Synthesis of Compound 19
Step 1) Synthesis of Compound 19-A
The above-mentioned compound 19-A (58.0 g,79.64% yield) was obtained by the same method as step 1 of the above-mentioned synthetic example 1 using 9, 9-diphenyl-9H-fluoren-4-amine (50.0 g,149.96 mmol) and 4-bromo-1, 1' -biphenyl (34.96 g,149.96 mmol).
Step 2) Synthesis of Compound 19
Using the compound 19-A (20.0 g,41.18 mmol) obtained in step 1 of the above-described synthesis example 19 and the compound 7-A (12.55 g,42.01 mmol) obtained in step 1 of the above-described synthesis example 7, the above-described compound 19 (24.2 g,78.56% yield) was obtained by the same method as in step 2 of the above-described synthesis example 1. (MS [ m+h ] + =748)
Synthesis example 20 Synthesis of Compound 20
Using the compound 19-A (20.0 g,41.18 mmol) obtained in step 1 of the above-described synthesis example 19 and the compound 10-A (12.55 g,42.01 mmol) obtained in step 1 of the above-described synthesis example 10, the above-described compound 20 (23.7 g,76.94% yield) was obtained by the same method as in step 2 of the above-described synthesis example 1. (MS [ m+h ] + =748)
Synthesis example 21 Synthesis of Compound 21
Using 9, 9-diphenyl-9H-fluoren-2-amine (15.0 g,44.99 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (24.64 g,92.22 mmol), the above-mentioned compound 21 (25.0 g,78.70% yield) was obtained by the same method as in step 2 of the above-mentioned synthetic example 7. (MS [ m+h ] + =706)
Synthesis example 22 Synthesis of Compound 22
Using 9, 9-diphenyl-9H-fluoren-2-amine (15.0 g,44.99 mmol) and the compound 7-A (27.56 g,92.22 mmol) obtained in step 1 of the above-described synthetic example 7, the above-described compound 22 (30.5 g,78.99% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =858)
Synthesis example 23 Synthesis of Compound 23
Using 9, 9-diphenyl-9H-fluoren-3-amine (15.0 g,44.99 mmol) and the compound 7-A (27.56 g,92.22 mmol) obtained in step 1 of the above-described synthetic example 7, the above-described compound 23 (29.0 g,75.11% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =858)
Synthesis example 24 Synthesis of Compound 24
Using 9, 9-diphenyl-9H-fluoren-4-amine (15.0 g,44.99 mmol) and the compound 7-A (27.56 g,92.22 mmol) obtained in step 1 of the above-described synthetic example 7, the above-described compound 24 (30.0 g,77.70% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =858)
Synthesis example 25 Synthesis of Compound 25
Using 9, 9-diphenyl-9H-fluoren-2-amine (15.0 g,44.99 mmol) and the compound 10-A (27.56 g,92.22 mmol) obtained in step 1 of the above-described synthetic example 10, the above-described compound 25 (29.0 g,75.11% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =858)
Synthesis example 26 Synthesis of Compound 26
Using 9, 9-diphenyl-9H-fluoren-4-amine (15.0 g,44.99 mmol) and the compound 10-A (27.56 g,92.22 mmol) obtained in step 1 of the above-described synthetic example 10, the above-described compound 26 (30.0 g,77.70% yield) was obtained by the same method as in step 2 of the above-described synthetic example 7. (MS [ m+h ] + =858)
Synthesis example 27 Synthesis of Compound 27
Using the compound 1-A (20.0 g,50.56 mmol) obtained in step 1 of synthesis example 1 and the compound 7-A (15.41 g,51.57 mmol) obtained in step 1 of synthesis example 7, the compound 27 (26.0 g,78.15% yield) was obtained by the same method as in step 2 of synthesis example 1. (MS [ m+h ] + =658)
Synthesis example 28 Synthesis of Compound 28
Step 1) Synthesis of Compound 28-A
Using 9, 9-dimethyl-9H-fluoren-4-amine (50.0 g,238.90 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (63.84 g,238.90 mmol), the above-mentioned compound 28-A (68.0 g,71.95% yield) was obtained by the same method as in step 1 of the above-mentioned synthetic example 1.
Step 2) Synthesis of Compound 28
Using the compound 28-A (20.0 g,50.56 mmol) obtained in step 1 of the above-described synthesis example 28, 4-bromo-1, 1' -biphenyl (12.02 g,51.57 mmol), the above-described compound 28 (21.5 g,77.63% yield) was obtained by the same method as step 2 of the above-described synthesis example 1. (MS [ m+h ] + =548)
Synthesis example 29 Synthesis of Compound 29
Using the compound 19-A (20.0 g,41.18 mmol) obtained in step 1 of the above-described synthesis example 19 and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (11.22 g,42.01 mmol), the above-described compound 29 (22.0 g,79.51% yield) was obtained by the same method as in step 2 of the above-described synthesis example 1. (MS [ m+h ] + =672)
< Experimental example and comparative experimental example >
Experimental example 1-1
ITO (indium tin oxide) toThe 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, a compound represented by the following formula HAT was preparedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, as a hole transport layer, a compound represented by the following chemical formula HT1 was used as a hole transport layerAfter vacuum deposition, the compound 1 produced in synthesis example 1 was used as an electron-inhibiting layer in the form ofIs subjected to thermal vacuum evaporation. Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were mixed at a weight ratio of 25:1 to giveVacuum evaporation was performed on the thickness of (c). Next, as a hole-suppressing layer, a compound represented by the following chemical formula HB1 was used asIs subjected to thermal vacuum evaporation. Next, as an electron injection and transport layer, a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ were mixed at a weight ratio of 1:1 to giveIs subjected to thermal vacuum evaporation. Next, lithium fluoride (LiF) is sequentially added to the electron injection and transport layer to form a lithium fluoride/lithium fluoride compositeTo aluminiumAnd vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device. /(I)
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 maintenanceThe 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.
Experimental examples 1-2 to 1-20
Organic light-emitting devices of examples 1-2 to 1-20 were fabricated in the same manner as in example 1-1 except that the compound described in table 1 below was used instead of compound 1 in example 1-1.
Comparative examples 1-1 to 1-5
Organic light emitting devices of comparative examples 1-1 to 1-5 were fabricated in the same manner as in example 1-1 except that the compound described in table 1 below was used instead of compound 1 in example 1-1.
When a current of 10mA/cm 2 was applied to the organic light emitting devices manufactured in the experimental examples and the comparative experimental examples, the voltage, efficiency, color coordinates, and life were measured, and the results thereof are shown in Table 1 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
As shown in table 1 above, it was confirmed that the compound of the present invention has excellent electron inhibitory ability, and an organic light emitting device using the same as an electron inhibitory layer shows remarkable effects in terms of driving voltage, efficiency and lifetime.
Specifically, the devices of examples 1-1 to 1-20 using the amine compound containing tetrahydronaphthalene substituted with an alkyl group and having fluorene as a substituent were confirmed to have a voltage decrease of at most about 15%, an efficiency increase of at most about 90%, and a lifetime increase of at most about 8.5 times as compared with the comparative example compounds EB1 to EB5 containing no tetrahydronaphthalene, or containing pyrenyl group, or having only a monocyclic or bicyclic aryl group.
Experimental examples 2-1 to 2-27 and comparative experimental examples 1-1 and 2-1 to 2-4
In the above-described experimental example 1-1, the organic light emitting devices of experimental examples 2-1 to 2-27 and comparative experimental examples 2-1 to 2-4 were fabricated in the same manner as in the above-described experimental example 1-1, except that the compound represented by the above-described chemical formula EB1 was used instead of the compound 1 as the electron-inhibiting layer and the compound represented by the above-described chemical formula HT1 was used instead of the compound represented by the following table 2 as the hole-transporting layer.
When a current of 10mA/cm 2 was applied to the organic light emitting devices manufactured in the experimental examples and the comparative experimental examples, the voltage, efficiency, color coordinates, and life were measured, and the results thereof are shown in Table 2 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 2
As shown in table 2 above, it was confirmed that the compound of the present invention has excellent hole transporting ability, and an organic light emitting device using the same as a hole transporting layer shows remarkable effects in terms of driving voltage, efficiency and lifetime.
Specifically, the devices of examples 2-1 to 2-27 using the amine compound having fluorene as a substituent containing tetrahydronaphthalene substituted with an alkyl group showed a decrease in voltage of at most about 15%, an increase in efficiency of at most about 42%, and a lifetime of at most about 3 times as compared with the comparative examples HT2 to HT5 containing no tetrahydronaphthalene, or having 2 amine groups substituted with a fluorenyl group, or having no alkyl group substituted with tetrahydronaphthalene.
Claims (12)
1. A compound represented by the following chemical formula 1:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
R1 to R4 are the same or different from each other and each independently is an alkyl group having 1 to 10 carbon atoms,
L1 to L3 are the same or different from each other and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms,
Ar1 is a phenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, a biphenyl group, a terphenyl group, a tetrabiphenyl group, a naphthyl group, a fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms, or a tetrahydronaphthyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms,
Ar11 and Ar12 are the same as or different from each other, and each independently is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ra is hydrogen, or deuterium, and is preferably hydrogen,
A to c are each integers of 0 to 3, and when a to c are each 2 or more, 2 or more L1 to L3 are each the same or different from each other,
P is an integer of 0 to 7, and when p is 2 or more, 2 or more Ra are the same or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4:
Chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
In the chemical formulas 1-1 to 1-4,
The definitions of R1 to R4, L1 to L3, ar1, ar11, ar12, ra, a to c, and p are the same as those in the chemical formula 1.
3. The compound according to claim 1, wherein the chemical formula 1 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,
The definitions of R1 to R4, L1 to L3, ar1, ar11, ar12, ra, a to c, and p are the same as those in the chemical formula 1.
4. The compound of claim 1, wherein R1 to R4 are methyl.
5. The compound of claim 1, wherein Ar1 is phenyl, biphenyl, terphenyl, tetralinyl, naphthyl, fluorenyl substituted or unsubstituted with methyl or phenyl, or tetrahydronaphthyl substituted or unsubstituted with methyl, substituted or tert-butyl.
6. The compound according to claim 1, wherein
The Ra is hydrogen.
7. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3-1 or 3-2:
Chemical formula 3-1
Chemical formula 3-2
In the chemical formulas 3-1 and 3-2,
R1 to R4, L1 to L3, ar11, ar12, ra, a to c and p are as defined in the chemical formula 1,
R5 to R8 are the same or different from each other and each independently is an alkyl group having 1 to 10 carbon atoms,
One of Rb is linked to L1,
Ar21 and Ar22 are the same as or different from each other, and each independently is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Rb which is not attached to L1 is hydrogen or deuterium,
Q is an integer of 0 to 7, and when q is 2 or more, 2 or more Rb are the same or different from each other.
8. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
9. An organic light emitting device, comprising: an anode, a cathode, and 1 or more organic layers disposed between the anode and the cathode, the 1 or more of the organic layers comprising the compound of any one of claims 1 to 8.
10. The organic light-emitting device of claim 9, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, the hole transport layer, or the hole injection and transport layer comprising the compound.
11. The organic light-emitting device of claim 9, wherein the organic layer comprises an electron-inhibiting layer comprising the compound.
12. The organic light-emitting device according to claim 9, wherein the organic layer comprises 1 or more of a hole transport layer, a hole injection layer, an electron suppression layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole suppression layer, and an electron injection and transport layer.
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| KR20160066308A (en) * | 2014-12-02 | 2016-06-10 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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| CN110835304A (en) * | 2018-08-17 | 2020-02-25 | 江苏三月光电科技有限公司 | Compound with spirofluorene structure as core, preparation method and application thereof |
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| DE102005026651A1 (en) * | 2005-06-09 | 2006-12-14 | Merck Patent Gmbh | New materials for organic electroluminescent devices |
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| TW201920343A (en) * | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | Materials for electronic devices |
| CN113228335A (en) * | 2019-07-31 | 2021-08-06 | 株式会社Lg化学 | Organic light emitting device |
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| KR20140076888A (en) * | 2012-12-13 | 2014-06-23 | 에스에프씨 주식회사 | aromatic compound having fused cyclic substituent in aromatic ring and organic light-emitting diode including the same |
| KR20160066308A (en) * | 2014-12-02 | 2016-06-10 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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