CN117796180A - Coating composition, organic light emitting device including the same, and method of manufacturing the same - Google Patents
Coating composition, organic light emitting device including the same, and method of manufacturing the same Download PDFInfo
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- CN117796180A CN117796180A CN202380013156.0A CN202380013156A CN117796180A CN 117796180 A CN117796180 A CN 117796180A CN 202380013156 A CN202380013156 A CN 202380013156A CN 117796180 A CN117796180 A CN 117796180A
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- coating composition
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
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- 230000008859 change Effects 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 150000004826 dibenzofurans Chemical class 0.000 description 1
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- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a coating composition, an organic light emitting device including the same, and a method for manufacturing the same.
Description
Technical Field
The present application claims priority and rights of korean patent application nos. 10-2022-0006600 and 10-2022-0006603 filed in the korean intellectual property office on 1 month 17 of 2022, the entire contents of which are incorporated herein by reference.
The present invention relates to a coating composition, an organic light emitting device including the same, and a method for manufacturing the same.
Background
The organic light emitting phenomenon is one of examples of converting current into visible rays through an internal process of a specific organic molecule. The principle of the organic light emitting phenomenon is as follows. When an organic material layer is disposed between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer are recombined to form excitons, and the excitons fall to a ground state again to emit light. An organic light emitting device utilizing this principle may generally be composed of a cathode, an anode, and organic material layers (e.g., a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer) disposed therebetween.
In order to manufacture an organic light emitting device in the related art, a deposition method is generally used. However, there are problems in that loss of material often occurs when an organic light emitting device is manufactured by a deposition method and it is difficult to manufacture a device having a large area, and in order to solve these problems, a device using a solution method has been developed.
Therefore, there is a need to develop materials for use in solution processes.
Disclosure of Invention
Technical problem
An object of the present invention is to provide an organic light emitting device including two or more blue host materials different from each other.
Another object of the present invention is to provide a method for manufacturing the above organic light emitting device.
Technical proposal
An exemplary embodiment of the present invention provides a coating composition including a compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2, and a solvent,
wherein the coating composition is used to form an organic material layer of an organic light emitting device.
[ chemical formula 1]
[ chemical formula 2]
In the chemical formula 1 and the chemical formula 2,
r1 and R2 are each unsubstituted or deuterium-substituted naphthyl,
r3 is a substituted or unsubstituted naphthyl,
r4 is- (L) a -R41，
L is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene,
R41 is a substituted or unsubstituted naphthyl,
a is an integer of 1 to 7, and when a is 2 or more, two or more L are the same or different from each other, and
the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are substituted with one or more deuterium.
Another exemplary embodiment of the present invention provides a coating composition including two or more host materials and a solvent that are different from each other,
wherein two or more host materials different from each other each comprise one or more deuterium,
the solubility of two or more host materials different from each other with respect to the solvent is each 70% or more,
the maximum emission peaks of the emission colors of two or more host materials different from each other are each 380nm to 500nm, and
any one of the two or more host materials different from each other is contained in an amount of 65 to 85 parts by weight with respect to 100 parts by weight of the two or more host materials different from each other.
Still another exemplary embodiment of the present invention provides an organic light emitting device, including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode,
Wherein the organic material layer having one or more layers comprises a light emitting layer, and
the light-emitting layer comprises the above-described coating composition.
Yet another exemplary embodiment of the present invention provides a method for manufacturing an organic light emitting device, the method including: preparing a first electrode;
forming an organic material layer having one or more layers on the first electrode; and
a second electrode is formed on the organic material layer having one or more layers,
wherein forming an organic material layer having one or more layers includes forming the organic material layer by a solution method using the above-described coating composition.
Advantageous effects
The organic light emitting device according to the present invention may be manufactured by a solution method.
The organic light emitting device according to the present invention may be obtained to have a low driving voltage, high efficiency, and/or excellent life characteristics.
Drawings
Fig. 1 to 3 are views illustrating structures of organic light emitting devices according to some exemplary embodiments of the present invention.
Fig. 4 shows the solubility of the coating composition 1 according to example 1-1 of the present invention.
101: substrate
201: anode
301: hole injection layer
401: hole transport layer
501: light-emitting layer
601: electron transport layer
701: electron injection layer
801: cathode electrode
901: cover layer
Detailed Description
Hereinafter, the present invention will be described in detail.
When one member (layer) is provided "on" another member (layer) in the present invention, this includes not only the case where one member (layer) is in contact with another member but also the case where another member (layer) is present between two members (layers).
When a portion "includes" one constituent element in the present invention, unless specifically described otherwise, this is not meant to exclude another constituent element, but means that another constituent element may also be included.
Hereinafter, the substituents of the present invention will be described in detail.
In the present invention, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent may be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
In the present invention, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halo groups, alkyl, cycloalkyl, aryl, and heteroaryl, or substituents that are unsubstituted or linked through two or more of the substituents exemplified above. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, biphenyl may also be aryl, and may be interpreted as a substituent to which two phenyl groups are linked.
Furthermore, in the present invention, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or a substituent which is unsubstituted or linked with two or more of the substituents exemplified above.
In the present invention, the halogen group is a fluorine group (-F), a chlorine group (-Cl), a bromine group (-Br) or an iodine group (-I).
In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but may be 1 to 30. According to an exemplary embodiment, the alkyl group has a carbon number of 1 to 20 or 1 to 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, and the like.
In the present invention, the number of carbon atoms of the cycloalkyl group is not particularly limited, but may be 3 to 60. According to an exemplary embodiment, the cycloalkyl group has a carbon number of 3 to 30 or 3 to 20. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.
In the present invention, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but may be 6 to 60. According to an exemplary embodiment, the aryl group has a carbon number of 6 to 30 or 6 to 20. Examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenylenyl,A radical, a fluorenyl radical, etc., but is not limited thereto.
In the present invention, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
When the fluorenyl group is substituted, the substituent may be a substituted fluorenyl group, such as a spirofluorenyl group, a 9, 9-dimethylfluorenyl group, and a diphenylfluorenyl group. However, the substituent is not limited thereto.
In the present invention, the heteroaryl group is an aromatic cyclic group containing one or more of N, O, P, S, si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited but may be 2 to 60. According to one exemplary embodiment, the heteroaryl group has a carbon number of 2 to 30. Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, and the like.
In the present invention, the above description of aryl groups is applied to arylene groups, except that arylene groups are divalent.
In the present invention, the above description of heteroaryl groups applies to heteroarylene groups, except that the heteroarylene group is divalent.
In the present invention, tg means glass transition temperature.
In the present invention, Δx means the difference in x between objects to be measured. For example, delta (Tg) for two materials means the difference in Tg between the two materials.
Hereinafter, a coating composition according to an exemplary embodiment of the present invention will be described.
An exemplary embodiment of the present invention provides a coating composition including a compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2, and a solvent, wherein the coating composition is used to form an organic material layer of an organic light emitting device.
[ chemical formula 1]
[ chemical formula 2]
In the chemical formula 1 and the chemical formula 2,
r1 and R2 are each unsubstituted or deuterium-substituted naphthyl,
r3 is a substituted or unsubstituted naphthyl,
r4 is- (L) a -R41，
L is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene,
r41 is a substituted or unsubstituted naphthyl,
a is an integer of 1 to 7, and when a is 2 or more, two or more L are the same or different from each other, and
the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are substituted with one or more deuterium.
In the present invention, the compounds represented by chemical formulas 1 and 2 are structurally different from each other.
When the organic material layer is formed using the coating composition according to the present invention including the compounds represented by chemical formulas 1 and 2 having different structures, the heat treatment temperature of the heat treatment step may be adjusted according to the process. In particular, when forming an organic material layer using a single host material or a coating composition including a single host material, the heat treatment temperature needs to be suitable only for the single host material, and when the temperature is outside a range of suitable heat treatment temperatures, for example, heat treatment is performed at a temperature higher than the corresponding heat treatment temperature, there is a disadvantage in that the host material or the organic material layer is crystallized. Therefore, there is a disadvantage in that the heat treatment temperature of the heat treatment step cannot be flexibly adjusted according to the process. In contrast, when the organic material layer is formed using the coating composition according to the present invention including the compounds represented by chemical formulas 1 and 2 having different structures, the heat treatment temperature of the heat treatment step may be flexibly adjusted according to the process. For example, the heat treatment temperature at the time of forming the organic material layer using the coating composition including the compound represented by chemical formulas 1 and 2 may be adjusted similarly to the heat treatment temperature at the time of forming the organic material layer using the coating composition including the red host material or the heat treatment temperature at the time of forming the organic material layer using the coating composition including the green host material.
Further, when an organic material layer or an organic light emitting device is manufactured using the coating composition including the compounds represented by chemical formulas 1 and 2 according to the present invention, the ratio of the parts by weight of the compounds represented by chemical formulas 1 and 2 may be flexibly adjusted. Therefore, when an organic material layer or an organic light emitting device is manufactured using a coating composition including the compound represented by chemical formulas 1 and 2, there are advantages in that: by adjusting the proportion of the compound contained in the organic material layer or the organic light emitting device, film characteristics can be improved, the maximum absorption wavelength can be optionally adjusted, brightness can be improved, and the like, and the heat treatment temperature required in the process can be optionally adjusted as described above.
Further, when the organic material layer is formed using the coating composition according to the present invention including two host materials having different structures, improvement in driving voltage, efficiency, and/or lifetime characteristics as device characteristics can be expected.
According to an exemplary embodiment of the present invention, the two host materials having different structures are a compound represented by chemical formula 1 and a compound represented by chemical formula 2.
According to an exemplary embodiment of the invention, R1 and R2 are each deuterium substituted or non-deuterium substituted naphthyl.
According to an exemplary embodiment of the invention, L is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene.
According to an exemplary embodiment of the invention, L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
According to an exemplary embodiment of the invention, L is an unsubstituted or deuterium-substituted arylene group having 6 to 60 carbon atoms; or unsubstituted or deuterium-substituted heteroarylene having 2 to 60 carbon atoms.
According to an exemplary embodiment of the invention, L is a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; substituted or unsubstituted divalent anthracenyl; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted divalent dibenzofuranyl group; or a substituted or unsubstituted divalent dibenzothienyl group.
According to an exemplary embodiment of the invention, L is unsubstituted or deuterium-substituted phenylene; unsubstituted or deuterium-substituted naphthylene; unsubstituted or deuterium-substituted divalent anthracenyl; unsubstituted or deuterium-substituted divalent fluorenyl; unsubstituted or deuterium-substituted divalent dibenzofuranyl groups; or unsubstituted or deuterium-substituted divalent dibenzothienyl.
According to an exemplary embodiment of the invention, R41 is substituted or unsubstituted naphthyl.
According to an exemplary embodiment of the invention, R41 is naphthyl, unsubstituted or substituted with any one or more substituents selected from the group consisting of: deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.
According to an exemplary embodiment of the invention, R41 is naphthyl, unsubstituted or substituted with any one or more substituents selected from the group consisting of: deuterium, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.
According to an exemplary embodiment of the invention, R41 is naphthyl, unsubstituted or substituted with any one or more substituents selected from deuterium, aryl and heteroaryl.
According to an exemplary embodiment of the invention, R41 is unsubstituted or deuterium substituted naphthyl.
According to an exemplary embodiment of the invention, R41 is unsubstituted or substituted or unsubstituted heteroaryl-substituted naphthyl.
According to an exemplary embodiment of the invention, R41 is unsubstituted or substituted or unsubstituted dibenzofuranyl substituted naphthyl.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 is any one selected from the following compounds.
In the compounds, the compounds are substituted with one or more deuterium.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 2 is any one selected from the following compounds.
In the compounds, the compounds are substituted with one or more deuterium.
In this specification, substitution of a compound with one or more deuterium means that at least one hydrogen ("H") is replaced with deuterium ("D"). For example, when the following compound a-1 is substituted with one or more deuterium, the compound may be represented by the following compound a-2 or a-3.
In the chemical formula a-2, z1 and z4 are each an integer of 0 to 7, z2 is an integer of 0 to 8, z3 is an integer of 0 to 4, and z1+z2+z3+z4 is an integer of 1 to 26.
In the present specification, dx means substituted with x deuterium (D), D x～y Meaning substituted with x to y deuterium. For example, D in formula a-3 1～26 Meaning substituted with 1 to 26 deuterium.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are deuterated by 10% or more.
According to an exemplary embodiment of the present invention, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 20% or more. In another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 30% or more. In still another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 40% or more. In still another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 50% or more. In still another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 60% or more. In one further exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 70% or more. In another further exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 80% or more. In still another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 90% or more. In still another exemplary embodiment, at least one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is deuterated by 100%.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 10% to 100%. In another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 20% to 100%. In yet another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 30% to 100%. In still another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 40% to 100%. In still another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 50% to 100%. In one further exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 60% to 100%. In another further exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 70% to 100%. In yet another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 80% to 100%. In still another exemplary embodiment, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 90% to 100%.
In the present invention, the term "deuterated" is intended to mean that at least one hydrogen ("H") has been replaced by deuterium ("D"). In deuterated compounds, deuterium is present at a natural abundance level of at least 100 times. In some exemplary embodiments, the compound is deuterated by at least 10%. The term "% deuterated" or "% deuterated" means the ratio of deuterium relative to the sum of protons+deuterium, and is expressed as a percentage.
In the present invention, deuterated materials may be prepared in a similar manner using deuterated precursor materials or more generally by treating non-deuterated materials with a deuterated solvent (e.g., benzene-D6) in the presence of a lewis acid H/D exchange catalyst (e.g., trifluoromethanesulfonic acid, aluminum trichloride, or ethylaluminum dichloride).
In the present invention, "deuteration rate" or "deuteration substitution rate" may be determined by a known method such as nuclear magnetic resonance (IH NMR), thin layer chromatography/mass spectrometry (TLC/MS), or gas chromatography/mass spectrometry (GC/MS).
As described above, when deuterium is substituted at a hydrogen position, the chemical properties of the compound are hardly changed. However, since deuterium has twice the atomic weight of hydrogen, the physical properties of deuterated compounds change. For example, deuterated compounds have a lower vibrational level, and a decrease in vibrational level can prevent a decrease in intermolecular van der Waals forces and a decrease in quantum efficiency due to collisions caused by intermolecular vibrations. Thus, devices comprising deuterated compounds have improved efficiency and lifetime.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each included in a weight ratio of 15:85 to 85:15.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are included in a weight ratio of 65:35 to 85:15 or in a weight ratio of 15:85 to 35:65.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are included in a weight ratio of 65:35 to 85:15.
According to an exemplary embodiment of the present invention, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are included in a weight ratio of 15:85 to 35:65.
According to a preferred exemplary embodiment of the present invention, when the total weight parts of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are set to 100 weight parts, the compound represented by chemical formula 1 is included in an amount of 15 to 35 weight parts or 65 to 85 weight parts. As a specific example, the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each contained at a weight ratio of 15:85 to 35:65 or 65:35 to 85:15.
According to an exemplary embodiment of the present invention, the coating composition includes a larger amount of the compound represented by chemical formula 1 than the amount of the compound represented by chemical formula 2.
According to an exemplary embodiment of the present invention, the coating composition includes a larger amount of the compound represented by chemical formula 2 than the amount of the compound represented by chemical formula 1.
The device including the compound represented by chemical formula 1 and the compound represented by chemical formula 2 at the above content has a long lifetime effect. In contrast, when the weight ratio is outside the above range, the service life of the organic light emitting device is shortened.
According to an exemplary embodiment of the present invention, the maximum emission peaks of the emission color of the compound represented by chemical formula 1 or the compound represented by chemical formula 2 are each 380nm to 500nm.
According to a preferred exemplary embodiment of the present invention, the maximum emission peaks of the emission colors of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each 380nm to 500nm.
In the present invention, the maximum emission peak of 380nm to 500nm means that the emission peak having the maximum height exists within 380nm to 500nm.
In the present invention, the emission color having a maximum emission peak of 380nm to 500nm is blue.
In the present invention, the measuring device for measuring the maximum emission peak may be a JASCO FP-8600 fluorescence spectrophotometer or the like. As a specific example, the fluorescence intensity and maximum emission peak can be measured at room temperature (about 300K) by: the material to be measured (the compound, the coating composition, a part of the organic material layer and/or a part of the device, etc.) is dissolved using toluene as a solvent to prepare a sample for fluorescence measurement, the sample solution is placed in a quartz cell, and then a fluorescence measurement device is used. However, the measuring device and the measuring conditions for measuring the maximum emission peak can be appropriately changed by those skilled in the art.
In the present invention, a peak refers to a point in the graph where the sign of the slope changes.
In the present invention, the height of a peak refers to a value obtained by subtracting the current value of the baseline from the current value of the corresponding peak in the cyclic voltammogram.
According to an exemplary embodiment of the present invention, the solubility of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 with respect to the solvent is each 70% or more.
In terms of solubility, since the coating composition according to one exemplary embodiment of the present invention is used when forming a single or multiple organic material layers of an organic light emitting device by a solution method, ink stability and the like are important factors. Specifically, the solubility of the material in the solvent in the coating composition determines whether the material can be used in an organic light emitting device for a solution process. When the solubility of the compound represented by chemical formula 1 and the compound represented by chemical formula 2, respectively, contained in the coating composition according to one exemplary embodiment of the present invention with respect to the solvent is 70% or more, a single-layer or multi-layer organic material layer of the organic light emitting device may be formed by a solution method. In contrast, when the solubility of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 with respect to the solvent is less than 70% each, the solution becomes cloudy, so that the compound cannot be used for manufacturing an organic light emitting device for a solution method, or long-term stability is significantly deteriorated even if the compound is used.
In the present invention, the solubility may be measured at 10℃to 30 ℃. According to a preferred exemplary embodiment, the solubility may be measured at 15 ℃ to 26 ℃.
According to an exemplary embodiment of the present invention, the solvent is exemplified as: for example, chlorine-based solvents such as chloroform, dichloromethane, 1, 2-dichloroethane, 1, 2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether-based solvents, e.g. tetrahydrofuran and diAn alkane; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; ketone-based solvents, e.g. acetone, methyl acetateEthyl ketone, cyclohexanone, isophorone, tetralone, decalin ketone, and acetylacetone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol and 1, 2-hexanediol, and derivatives thereof; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; and solvents such as tetralin, but are not limited thereto.
According to an exemplary embodiment of the present invention, the solvent may be used alone or as a mixture of two or more solvents.
According to an exemplary embodiment of the present invention, the coating composition is used to form an organic material layer of an organic light emitting device.
According to an exemplary embodiment of the present invention, the coating composition is used to form a single or multiple organic material layers of an organic light emitting device.
According to an exemplary embodiment of the present invention, the coating composition is used to form a single organic material layer of an organic light emitting device.
According to an exemplary embodiment of the present invention, the coating composition is used to form a multi-layered organic material layer of an organic light emitting device.
According to an exemplary embodiment of the present invention, the organic material layer is a light emitting layer. That is, the coating composition is used to form a light emitting layer.
According to an exemplary embodiment of the present invention, the difference in HOMO level or LUMO level between the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 0.1eV to 5.0eV. Specifically, the difference in HOMO level or LUMO level between the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 0.1eV to 4.0eV or 0.1eV to 3.0eV.
According to an exemplary embodiment of the present invention, the difference in HOMO levels of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 0.1eV to 5.0eV, 0.1eV to 4.0eV, or 0.1eV to 3.0eV.
According to an exemplary embodiment of the present invention, the difference in LUMO levels of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 0.1eV to 5.0eV, 0.1eV to 4.0eV, or 0.1eV to 3.0eV.
In the present invention, the energy level means the magnitude of energy. Therefore, even when the energy level is expressed in the negative (-) direction of the vacuum level, it is interpreted that the energy level means the absolute value of the corresponding energy value. For example, HOMO level (HOMO energy level) means the distance from the vacuum level to the highest occupied molecular orbital. Further, LUMO level (LUMO energy level) means a distance from a vacuum level to a lowest unoccupied molecular orbital.
In this specification, the difference in HOMO energy level and the difference in LUMO energy level are expressed as absolute values. For example, the difference in HOMO level of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is |homo level of the compound represented by chemical formula 1-HOMO level of the compound represented by chemical formula 2|, and the value thereof is 0.1eV to 5.0eV.
In the present invention, when the light emitting layer is composed of a host-guest system, holes and electrons are injected into HOMO level and LUMO level of a host material, respectively, to cause Langevin-type recombination, so that excitons are first generated in the host material, and excitons are sequentially formed in a dopant material by energy transfer, and thus, light can be finally emitted from the dopant material. In this case, when the difference in HOMO level or LUMO level of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is within the above-described range, the compound contributes to light emission of the device, and thus, the device has excellent light emission efficiency.
According to an exemplary embodiment of the present invention, the difference in glass transition temperature (Tg) between the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 3 to 30 ℃. Specifically, the difference in Tg between the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 4 ℃ to 30 ℃, 4 ℃ to 28 ℃, or 4 ℃ to 10 ℃.
The difference in Tg is expressed as absolute value. For example, the difference in glass transition temperature (Tg) of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is |tg of the compound represented by chemical formula 1-Tg of the compound represented by chemical formula 2|, and the value thereof is 4 ℃ to 30 ℃.
According to an exemplary embodiment of the present invention, the compounds represented by chemical formulas 1 and 2 are each used as a host. Specifically, the compounds represented by chemical formulas 1 and 2 are each used as a light-emitting body.
According to an exemplary embodiment of the present invention, the coating composition may further comprise a light emitting dopant.
Examples of luminescent dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene having an arylamine group,Bisindenopyrene, and the like. Further, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but are not limited thereto. Further, examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
The light emitting dopant material may be included in an amount of 0.5 to 20 parts by weight, 0.7 to 10 parts by weight, or 0.8 to 5 parts by weight with respect to 100 parts by weight of the light emitting host material.
According to an exemplary embodiment of the present invention, the coating composition may be in a liquid phase.
According to another exemplary embodiment of the present invention, the coating composition further comprises: single molecules containing photocurable groups and/or thermosetting groups or single molecules containing end groups capable of forming polymers by heat. As described above, the single molecule containing a photocurable group and/or a thermosetting group or the single molecule containing a terminal group capable of forming a polymer by heat may be a compound having a molecular weight of 3,000g/mol or less, but the molecular weight is not limited to the exemplified molecular weight.
A single molecule containing a photocurable group and/or a thermosetting group or a single molecule containing a terminal group capable of forming a polymer by heat may mean an aryl group such as phenyl, biphenyl, fluorene, and naphthalene; aryl amines; or a single molecule in which fluorene is substituted with a photocurable and/or thermosetting group or end groups capable of forming a polymer by heat.
According to an exemplary embodiment of the invention, the coating composition has a viscosity of 2cP to 15cP at room temperature. When the above viscosity is satisfied, the device is easily manufactured. In particular, when an organic material layer in an organic light emitting device is formed, a uniform film can be formed.
An exemplary embodiment of the present invention provides a coating composition including two or more host materials and solvents different from each other,
wherein two or more host materials different from each other each comprise one or more deuterium,
the solubility of two or more host materials different from each other with respect to the solvent is each 70% or more,
the maximum emission peaks of the emission colors of two or more host materials different from each other are each 380nm to 500nm, and
any one of the two or more host materials different from each other is contained in an amount of 65 to 85 parts by weight with respect to 100 parts by weight of the two or more host materials different from each other.
According to an exemplary embodiment of the present invention, two or more host materials different from each other include the compound represented by chemical formula 1 described above and the compound represented by chemical formula 2 described above.
According to an exemplary embodiment of the present invention, the coating composition comprises two host materials that are different from each other.
In the coating composition, the solubility and emission peaks are described above.
Hereinafter, an organic light emitting device according to an exemplary embodiment of the present invention will be described.
An exemplary embodiment of the present invention provides an organic light emitting device, including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein the organic material layer having one or more layers includes a light emitting layer, and the light emitting layer includes the coating composition.
The organic light emitting device according to one exemplary embodiment of the present invention as described above has a high charge recombination probability, so that excellent light emitting efficiency can be expected. Further, since two or more blue host materials different from each other are contained, there is an advantage in that it is advantageous to ensure a process temperature.
According to an exemplary embodiment of the present invention, two or more blue host materials different from each other include a compound represented by chemical formula 1 and a compound represented by chemical formula 2.
In the present specification, comprising the coating composition means comprising the coating composition or a cured product of the coating composition.
In this specification, the fact that the light emitting layer includes a coating composition means that the light emitting layer is formed using the coating composition.
Hereinafter, the types of the organic material layers included in the above-described organic light emitting device will be specifically described.
The organic material layer having one or more layers includes one or more layers selected from the group consisting of: for example, a hole injection layer; a hole transport layer; a hole injection and transport layer; an electron blocking layer; a light emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; an electron injection and transport layer; etc. In this case, the hole injection and transport layer means a layer that simultaneously injects and transports holes. Further, the electron injection and transport layer means a layer that simultaneously injects and transports electrons. However, the organic material layers forming the group are only one example, and the organic material layer having one or more layers is not limited to the above-described example. Further, if necessary, the organic material layer having one or more layers may include two or more layers functioning the same. An organic light emitting device according to one exemplary embodiment includes a first light emitting layer and a second light emitting layer. However, the organic material layer having one or more layers is not limited to the example.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers includes a light emitting layer. As one example, the light emitting layer comprises the coating composition described above.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes an organic material layer having one or more layers other than the light emitting layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes an organic material layer having one or more layers selected from the group consisting of: a hole injection layer; a hole transport layer; a hole injection and transport layer; an electron injection layer; an electron transport layer; and an electron injection and transport layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes an organic material layer having one or more layers selected from the group consisting of: a hole injection layer; a hole transport layer; and a hole injection and transport layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes a first organic material layer other than the light emitting layer.
According to an exemplary embodiment of the present invention, the first organic material layer is an organic material layer having one or more layers selected from: a hole injection layer; a hole transport layer; and a hole injection and transport layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes an organic material layer having one or more layers selected from the group consisting of: an electron injection layer; an electron transport layer; and an electron injection and transport layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes a second organic material layer other than the light emitting layer.
According to an exemplary embodiment of the present invention, the second organic material layer is an organic material layer having one or more layers selected from: an electron injection layer; an electron transport layer; and an electron injection and transport layer.
According to an exemplary embodiment of the present invention, the organic material layer having one or more layers further includes a first organic material layer and a second organic material layer,
the first organic material layer is disposed between the first electrode and the light emitting layer,
The second organic material layer is disposed between the second electrode and the light emitting layer,
the first organic material layer is an organic material layer having one or more layers selected from: a hole injection layer; a hole transport layer; and a hole injection and transport layer
The second organic material layer is an organic material layer having one or more layers selected from: an electron injection layer; an electron transport layer; and an electron injection and transport layer.
Hereinafter, a stacked structure of the organic material layer and the organic light emitting device including the organic material layer will be described in detail.
The organic material layer of the organic light emitting device according to one exemplary embodiment of the present invention has a single layer structure. For example, an organic material layer having a single-layer structure is disposed between the first electrode and the second electrode of the organic light emitting device, and the organic material layer contains the above-described coating composition. According to a specific exemplary embodiment, the organic material layer having a single-layer structure is a light emitting layer, and in this case, the light emitting layer contains the above-described coating composition.
The organic material layer of the organic light emitting device according to another exemplary embodiment of the present invention has a multi-layer structure in which organic material layers having two or more layers are stacked. For example, an organic material layer having a multi-layered structure is disposed between a first electrode and a second electrode of an organic light emitting device.
According to an exemplary embodiment of the present invention, the organic material layer having a multi-layered structure includes a light emitting layer and an organic material layer other than the light emitting layer. As one example, a light emitting layer is provided between the first electrode and the second electrode, and an organic material layer other than the light emitting layer is provided between the first electrode and the light emitting layer. As another example, a light emitting layer is provided between the first electrode and the second electrode, and an organic material layer other than the light emitting layer is provided between the light emitting layer and the second electrode. As yet another example, a light emitting layer is provided between a first electrode and a second electrode, any organic material layer other than the light emitting layer is provided between the first electrode and the light emitting layer, and any other organic material layer other than the light emitting layer is provided between the light emitting layer and the second electrode. However, the above structure is only one example, and the structure is not limited to the above structure. Further, the organic material layer other than the light emitting layer may be one or more layers selected from: for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection and transport layer, and the like, but is not limited thereto.
In general, a hole injection layer, a hole transport layer, or an electron blocking layer in an organic light emitting device is disposed between an anode and a light emitting layer. As a specific example, a hole injection layer is provided on the anode, a hole transport layer is provided on the hole injection layer, and an electron blocking layer is provided on the hole injection layer, but the present invention is not limited to the above example.
In addition, generally, an electron injection layer, an electron transport layer, or a hole blocking layer in an organic light emitting device is disposed between a cathode and a light emitting layer. As a specific example, a hole blocking layer is provided on the light emitting layer, an electron transporting layer is provided on the hole blocking layer, and an electron injecting layer is provided on the electron transporting layer, but the present invention is not limited to the above example.
The organic material layer having a multi-layered structure included in the organic light emitting device according to an exemplary embodiment of the present invention includes: a light emitting layer; and a first 'organic material layer having one or more layers selected from a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer, the light emitting layer being disposed between the first electrode and the second electrode, and the first' organic material layer having one or more layers being disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.
The organic material layer having a multi-layered structure included in the organic light emitting device according to an exemplary embodiment of the present invention includes: a light emitting layer; a first' organic material layer having one or more layers selected from a hole injection layer, a hole transport layer, and an electron blocking layer; and a second ' organic material layer having one or more layers selected from an electron injection layer, an electron transport layer, and a hole blocking layer, the light emitting layer being disposed between the first electrode and the second electrode, the first ' organic material layer having one or more layers being disposed between the first electrode and the light emitting layer, and the second ' organic material layer having one or more layers being disposed between the second electrode and the light emitting layer.
According to an exemplary embodiment of the invention, the first electrode is an anode and the second electrode is a cathode.
According to another exemplary embodiment of the invention, the first electrode is a cathode and the second electrode is an anode.
According to an exemplary embodiment of the present invention, the organic light emitting device may be a normal organic light emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.
According to another exemplary embodiment of the present invention, the organic light emitting device may be an inverted organic light emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.
For example, the structure of the organic light emitting device of the present specification may be the structure shown in fig. 1 to 3, but is not limited thereto.
Fig. 1 shows an example of an organic light-emitting device constituted by a first electrode (in this case, an anode) 201, a light-emitting layer 501, and a second electrode (in this case, a cathode) 801.
Fig. 2 shows an example of an organic light-emitting device constituted by the substrate 101, the anode 201, the hole injection layer 301, the hole transport layer 401, the light-emitting layer 501, the electron transport layer 601, the electron injection layer 701, and the cathode 801.
Fig. 3 shows an example of an organic light-emitting device constituted by the substrate 101, the anode 201, the hole injection layer 301, the hole transport layer 401, the light-emitting layer 501, the electron transport layer 601, the electron injection layer 701, the cathode 801, and the capping layer 901.
The light emitting layer 501 of fig. 1 to 3 includes a coating composition containing two host materials (a compound represented by chemical formula 1 and a compound represented by chemical formula 2) different from each other and a solvent, or may be formed using the coating composition.
As described above, the organic light emitting device having the organic material layer having a single-layer or multi-layer structure may have, for example, the following stacked structure, but the stacked structure 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 blocking layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer
(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer
In the structure, "hole injection layer/hole transport layer" may be replaced with "hole injection and transport layer". In addition, the "electron transport layer/electron injection layer" may be replaced by the "electron injection and transport layer".
In the organic light emitting device according to an exemplary embodiment of the present invention, the description of the compound represented by chemical formula 1, the compound represented by chemical formula 2, and the solvent is as described above in the coating composition. For example, the above description may be applied with respect to the solubility of the host material (the compound represented by chemical formula 1 and the compound represented by chemical formula 2), the maximum emission peak of the emission color of the host material, the weight ratio, the deuteration rate, the difference in HOMO energy level, the difference in LUMO energy level, and the difference in Tg.
Hereinafter, materials for the anode, the cathode, and the specific organic material layer will be described in detail.
As the anode material, a material having a high work function is generally preferable to promote hole injection into the organic material layer. Examples thereof include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO, al or SnO 2 Sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)](PEDOT), polypyrrole and polyaniline; etc., but is not limited thereto.
As the cathode material, a material having a low work function is generally preferable to promote electron injection into the organic material layer. Examples thereof include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials, e.g. LiF/Al or LiO 2 Al; etc., but is not limited thereto.
According to an exemplary embodiment of the present invention, the anode and/or the cathode may also each be composed of three layers having a stack structure of ITO/Ag/ITO. In this case, when the first electrode and/or the second electrode is formed of multiple layers, voltage drop due to signal delay (RC delay) can be minimized. Accordingly, a desired voltage can be efficiently transmitted to the light emitting device.
A capping layer (CPL) for protecting the electrode may be additionally formed on the cathode, and as a material for the capping layer, a material used in the art may be appropriately used.
The light emitting layer may comprise a host material and/or a dopant material.
Examples of host materials include fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and specific examples of the heterocycle-containing compound include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples are not limited thereto.
According to an exemplary embodiment of the present invention, as the host material, a mixture of two or more host materials selected from the above-described host materials may be used. Specifically, anthracene derivatives can be used. More specifically, a mixture of the compound of chemical formula 1 and the compound of chemical formula 2 may be used as a host material.
As dopant materials, the descriptions exemplified in the coating composition may be applied.
The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has a capability of transporting holes, and has an effect of receiving holes from the anode and a hole injection effect excellent for the light emitting layer or the light emitting material. Further, the hole injection material is preferably a material excellent in the ability to prevent excitons generated by the light emitting layer from moving to the electron injection layer or the electron injection material. The hole injection material is preferably a material excellent in the capability of forming a thin film. Further, the HOMO of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include: metalloporphyrins, oligothiophenes, and arylamine-based organic materials; organic materials based on hexanitrile hexaazatriphenylene; organic materials based on quinacridones; perylene-based organic materials; polythiophene-based conductive polymers such as anthraquinone and polyaniline; ytterbium (Yb); dysprosium (Dy); etc., but is not limited thereto.
The hole transport layer is a layer in which: which receives holes from the hole injection layer and transfers the holes to the light emitting layer, and may have a single layer structure or a multi-layer structure having two or more layers. The hole transport layer is preferably a material having high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting material is preferably a material having high electron mobility that can well receive electrons from the cathode and transfer the electrons to the light emitting layer. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq 3 Is a complex of (a) and (b); an organic radical compound; hydroxyflavone-metal complexes; etc., but is not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the relevant art. In particular, suitable cathode materials are typical materials with a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material is excellent in the ability to transport electrons and has an effect of receiving electrons from the cathode and an electron injecting effect excellent for the light emitting layer or the light emitting material. Further, the electron injection material is preferably a material that prevents excitons generated by the light emitting layer from moving to the hole injection layer and is excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto. Examples of metal complex compounds include 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), and bis (10-hydroxybenzo [ h ]]Quinoline (quinoline)) Beryllium, bis (10-hydroxybenzo [ h ]]Quinoline) zinc, bis (2-methyl-8-quinoline) chlorogallium, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The electron blocking layer is a layer that can improve the lifetime or efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and into the hole injection layer. As the electron blocking material, a known electron blocking material may be used.
The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specific examples of hole blocking layer materials includeThe diazole derivative or triazole derivative, phenanthroline derivative, aluminum complex, and the like, but is not limited thereto.
The hole injection and transport layer may comprise materials for the hole injection layer and the hole transport layer described above.
The electron injection and transport layer may comprise materials for the electron injection layer and the hole transport layer described above.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a dual emission type depending on materials to be used.
Hereinafter, a method for manufacturing an organic light emitting device according to an exemplary embodiment of the present invention will be provided.
An exemplary embodiment of the present invention provides a method for manufacturing an organic light emitting device, in which one or more layers of organic material layers of the organic light emitting device are formed using the above-described coating composition.
Specifically, an exemplary embodiment of the present invention provides a method for manufacturing an organic light emitting device, the method including: preparing a first electrode; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer having one or more layers, wherein forming the organic material layer having one or more layers includes forming the organic material layer by a solution method using the coating composition.
According to an exemplary embodiment of the present invention, the organic light emitting device may be manufactured by materials and methods known in the art, except that the organic material layer having one or more layers is formed of the above-described coating composition. In particular, the organic light emitting device may be manufactured by materials and methods known in the art, except that the light emitting layer is formed of the above-described coating composition.
In the case of the coating composition according to one exemplary embodiment of the present specification, an organic light emitting device may be manufactured by a solution application method, thereby realizing a large-area device.
According to an exemplary embodiment of the present invention, forming the organic material layer having one or more layers using the coating composition uses spin coating.
According to another exemplary embodiment of the present invention, forming an organic material layer having one or more layers using a coating composition uses a printing method.
Examples of printing methods according to an exemplary embodiment of the present invention include inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, and the like, but are not limited to the printing methods listed above.
The coating composition according to one exemplary embodiment of the present invention is suitable for a solution process due to its structural characteristics such that the organic material layer can be formed by a printing process, and thus, there is an economical effect in terms of time and cost when manufacturing a device.
According to an exemplary embodiment of the present invention, forming an organic material layer using a coating composition includes: applying a coating composition on the first electrode or the organic material layer having one or more layers; and drying, heat treating or light treating the coated coating composition.
According to an exemplary embodiment of the present invention, forming an organic material layer having one or more layers using a coating composition includes: applying a coating composition on the first electrode or the organic material layer having one or more layers; and drying, heat treating or light treating the coated coating composition. Preferably, forming the organic material layer having one or more layers using the coating composition includes: coating an organic material layer having one or more layers with a coating composition; and drying or heat-treating the applied coating composition. As one example, forming an organic material layer having one or more layers using a coating composition includes: coating a first electrode or an organic material layer having one or more layers with a coating composition; and drying the applied coating composition. As another example, forming an organic material layer having one or more layers using a coating composition includes: coating a first electrode or an organic material layer having one or more layers with a coating composition; and heat treating the applied coating composition. As yet another example, forming an organic material layer having one or more layers using a coating composition includes: coating an organic material layer having one or more layers with a coating composition; drying the applied coating composition; and heat treating the coating composition.
According to an exemplary embodiment of the present invention, the heat treatment of the coating composition may be performed by heat treatment, and the heat treatment temperature of the heat treatment step may be 80 to 250 ℃;80 ℃ or higher and lower than 200 ℃;100 ℃ to 170 ℃; or 120 ℃ to 160 ℃.
According to an exemplary embodiment of the present invention, the heat treatment time of the heat treatment step is 1 minute to 2 hours, and according to an exemplary embodiment, may be 1 minute to 1 hour, and in another exemplary embodiment, may be 5 minutes to 1 hour. As a preferred example, the heat treatment time of the heat treatment step is 5 minutes to 30 minutes.
When the formation of the organic material layer having one or more layers formed using the coating composition includes heat treatment or light treatment of the coated coating composition, and the coating composition further includes a single molecule including a photocurable group and/or a thermosetting group or a single molecule including a terminal group capable of forming a polymer by heat, the organic material layer including a thin film structure may be provided by forming a cross-linking bond between components included in the coating composition. In this case, when another layer is stacked on the surface of the organic material layer formed using the coating composition, the organic material layer can be prevented from being dissolved by a solvent, morphologically affected by the solvent, or decomposed by the solvent. Therefore, when the organic material layer is formed by the manufacturing method, the resistance to a solvent increases, so that a plurality of layers can be formed by repeating the solution deposition and the crosslinking method, and the stability increases, so that the life characteristics of the device can be increased.
An exemplary embodiment of the present invention provides an electronic device including an organic light emitting device including the above-described coating composition or an organic material layer formed using the above-described coating composition.
The electronic device may include all of the following: interlayer insulating films of semiconductor devices, color filters, black matrices, overcoat layers, column spacers, passivation films, buffer coating films, multilayer printed board insulating films, overcoat layers of flexible copper-clad boards, buffer coating films, multilayer printed board insulating films, solder resist films, insulating films of OLEDs, protective films of thin film transistors of liquid crystal display devices, electrode protective films and semiconductor protective films of organic EL devices, OLED insulating films, LCD insulating films, semiconductor insulating films, solar light modules, touch panels, display devices such as display panels, and the like, but are not limited thereto.
EMBODIMENTS FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described with reference to examples for specifically describing the present invention. However, the embodiments according to the present invention may be modified into various different forms, and the scope of the present invention should not be construed as being limited to the embodiments to be described below. The embodiments of the present invention are provided to more fully describe the present invention to those of ordinary skill in the art.
< preparation example of Compound >
Preparation example 1 preparation of Compound D
9-bromo-10- (naphthalen-2-yl) anthracene (20 g,52.2 mmol) and (4- (naphthalen-1-yl) phenyl) boronic acid (14.2 g,57.4 mmol) were placed in 200mL of tetrahydrofuran solvent and the resulting mixture was warmed and stirred. After an aqueous solution of potassium carbonate (14.4 g,104.3 mmol) was added thereto, tetrakis (triphenylphosphine) palladium (0) (1.81 g,1.56 mmol) was added thereto at the start of distillation, and the resulting mixture was stirred for another 3 hours. After the reaction was completed, the resulting product was filtered and then subjected to EtOH slurry distillation to obtain [ compound D-1 ]](23 g,87% yield). In the process of preparing [ Compound D-1 ]]After dissolution in benzene-d 6 in an inert environment, the resulting solution was stirred with trichlorobenzene for 2 hours. Through D 2 O quenching terminates the reaction to give [ Compound D]。
[ Compound D ]]Tg of 131 c and [ compound D ]]The HOMO and LUMO levels of (C) were-5.89 eV and-2.92 eV, respectively. In the reaction scheme, dn means substituted with n deuterium (D), e.g., D 7 Meaning substituted with 7 deuterium.
[M+H] + ＝533
Preparation example 2 preparation of Compound E
A [ Compound E ] was produced in the same manner as in production example 1, except that naphthalene-1-ylboronic acid was used in production example 1 instead of (4- (naphthalen-1-yl) phenyl) boronic acid.
[ Compound E]Is 126 ℃ and [ Compound E ]]The HOMO and LUMO levels of (C) were-6.00 eV and-3.05 eV, respectively. In the reaction scheme, dn means substituted with n deuterium (D), e.g., D 7 Meaning substituted with 7 deuterium.
[M+H] + ＝453
* Absolute value of difference in Tg/absolute value of difference in HOMO energy level/absolute value of difference in LUMO energy level between Compound D and Compound E
△(Tg)：5℃
Delta (HOMO level): 0.11eV
Delta (LUMO energy level): 0.13eV
Example 1-1.
The following compound D and the following compound E were mixed in a weight ratio of 7:3, and cyclohexanone solvent was added thereto to prepare a coating composition 1. The degree of dissolution of compound D and compound E in the coating composition 1 prepared above in the solvent cyclohexanone was judged by photographs. Fig. 4 shows a photograph for judging the degree of dissolution of compound D and compound E in the solvent cyclohexanone in example 1-1 of the present application.
From fig. 4, it can be confirmed that the coating composition 1 is not cloudy since the compound D and the compound E show excellent solubility (solubility of 70% or more) for cyclohexanone which is a solvent. From this, it was confirmed that the stability of the coating composition 1 was excellent.
< device manufacturing example >
Thin coating with a thickness ofAnd- >The glass substrate of Indium Tin Oxide (ITO)/Ag/ITO as an anode was put into distilled water in which a detergent was dissolved, and subjected to ultrasonic washing. In this case, a product manufactured by Fischer co. Was used as a cleaner, and distilled water filtered twice using a filter manufactured by Millipore co. Was used as distilled water. After washing the glass substrate for 30 minutes, ultrasonic washing was repeated twice using distilled water for 10 minutes. After washing with distilled water, the substrate was washed with isopropyl groupThe solvent was ultrasonically washed, dried, then baked on a hot plate for 10 minutes, and then transferred to a glove box.
A Hole Injection Layer (HIL) solution was spin-coated (2500 rpm) on an anode with a mixture comprising 2.5 wt% cyclohexanone of the following compound a and the following compound B in a weight ratio of 8:2, and heat-treated (cured) at 230 ℃ for 30 minutes to form a Hole Injection Layer (HIL) having a thickness of 50 nm. Thereafter, a Hole Transport Layer (HTL) solution was prepared from the following compound C in 2.1% w/V toluene solvent, thereby forming a Hole Transport Layer (HTL) having a thickness of 100nm on the HIL by spin coating.
Subsequently, a light emitting layer (EML) having a thickness of 40nm was formed on the hole transport layer, and in this case, the following compound D and the following compound E, which are two blue hosts, were mixed at a weight ratio of 7:3, and a blue dopant compound F and cyclohexanone were mixed in the mixture at a ratio of 2 wt%, to prepare a light emitting layer (EML) coating composition, and the coating composition was spin-coated, and then heat-treated on a hot plate at 150 ℃ for 10 minutes to manufacture a light emitting layer having a thickness of 40 nm. The following compound G was vacuum deposited on the light emitting layer, thereby forming an electron transport layer having a thickness of 20 nm. On the electron transport layer, yb was sequentially deposited to form an electron injection layer having a thickness of 1nm, and Ag: mg was deposited to a thickness of 13nm at a ratio of 9:1 to form a cathode, and finally the following compound H was applied on the cathode, thereby forming a capping layer having a thickness of 70 nm.
In the above step, the deposition rate of the organic material is maintained atTo->The deposition rates of the electron injection layer and the cathode are maintained at +.>And->And the vacuum degree during deposition is maintained at 2×10 -8 To 5X 10 -6 And (5) a bracket.
/>
/>
Example 2-1.
For the organic light-emitting device manufactured in the device manufacturing example, the temperature was 10mA/cm 2 The results of measuring the driving voltage, the light emitting efficiency, the external quantum efficiency and the service life at the current density of (2) are shown in table 1 below. T95 means the time (hours) taken for the luminance to decrease to 95% of the initial luminance (1000 nit).
Examples 2-2 and comparative examples 2-1 to 2-4.
An organic light-emitting device was manufactured in the same manner as in example 2-1, except that the compounds shown in table 1 below were used instead of the compound D and the compound E contained in the light-emitting layer (EML) coating composition used during the manufacture of the light-emitting layer.
Compounds D-1 and E-1 used in comparative examples 2-3 and 2-4, respectively, were as follows.
For each of the organic light-emitting devices manufactured in examples or comparative examples, a current of 10mA/cm was measured 2 The results of measuring the driving voltage, the light emitting efficiency, the external quantum efficiency and the service life at the current density of (2) are shown in table 1 below.
TABLE 1
As shown in table 1, it can be determined that in examples 2-1 and 2-2 in which the organic material layer was formed using the coating composition according to the present invention including two host materials different from each other, the driving voltage was reduced and the efficiency and the service life characteristics were improved, as compared with comparative examples 2-1 to 2-6.
Specifically, it can be confirmed that in examples 2-1 and 2-2, by using the coating composition including two blue host materials different from each other substituted with deuterium to form an organic material layer, the driving voltage is reduced and the efficiency and the service life characteristics are improved, as compared with the case of using the coating composition including two blue host materials different from each other not substituted with deuterium (comparative examples 2-1 and 2-2).
Further, it was confirmed that in comparative examples 2-3 to 2-6, the organic material layer was formed using the coating composition containing no two blue host materials different from each other but a single blue host material, resulting in deterioration of driving voltage, efficiency, and/or service life characteristics. In particular, in comparative examples 2-3 and 2-5, the organic material layer was formed using the coating composition containing only the compound E or the compound E-1, but it could be confirmed that the organic layer crystallized, and thus, the device characteristics were deteriorated so much that the voltage, efficiency, and service life characteristics could not be measured. Further, in comparative examples 2-4 and 2-6, the organic material layer was formed using the coating composition containing only the compound D or the compound D-1, but it was confirmed that there was a disadvantage that: the driving voltage increases and the efficiency decreases, and in particular, the service life characteristics are greatly deteriorated.
Claims (17)
1. A coating composition comprising a compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2, and a solvent,
wherein the coating composition is used to form an organic material layer of an organic light emitting device:
[ chemical formula 1]
[ chemical formula 2]
In the chemical formula 1 and the chemical formula 2,
r1 and R2 are each unsubstituted or deuterium-substituted naphthyl,
r3 is a substituted or unsubstituted naphthyl,
r4 is- (L) a -R41，
L is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene,
r41 is a substituted or unsubstituted naphthyl,
a is an integer of 1 to 7, and when a is 2 or more, two or more L are the same or different from each other, and
the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each substituted with one or more deuterium.
2. The coating composition of claim 1, wherein L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
3. The coating composition according to claim 1, wherein the solubility of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 with respect to the solvent is each 70% or more.
4. The coating composition according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
in the compounds, the compounds are substituted with one or more deuterium.
5. The coating composition according to claim 1, wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
in the compounds, the compounds are substituted with one or more deuterium.
6. The coating composition according to claim 1, wherein the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each contained in a weight ratio of 15:85 to 85:15.
7. The coating composition of claim 1, wherein the organic material layer is a light emitting layer.
8. The coating composition according to claim 1, wherein the maximum emission peaks of the emission colors of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each 380nm to 500nm.
9. The coating composition of claim 1, wherein the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are each deuterated by 10% or more.
10. The coating composition according to claim 1, wherein a difference in HOMO level or LUMO level of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 0.1eV to 5.0eV.
11. The coating composition according to claim 1, wherein a difference in glass transition temperature between the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 3 ℃ to 30 ℃.
12. A coating composition comprising two or more host materials and solvents which are different from each other,
wherein the two or more host materials different from each other each comprise one or more deuterium,
the two or more host materials different from each other each have a solubility of 70% or more with respect to the solvent,
the maximum emission peaks of the emission colors of the two or more host materials different from each other are each 380nm to 500nm, and
any one of the two or more host materials different from each other is contained in an amount of 65 to 85 parts by weight with respect to 100 parts by weight of the two or more host materials different from each other.
13. An organic light emitting device comprising:
a first electrode;
A second electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the organic material layer having one or more layers includes a light emitting layer, and
the light-emitting layer comprises the coating composition according to any one of claims 1 to 12.
14. The organic light-emitting device of claim 13, wherein the organic material layer having one or more layers further comprises an organic material layer having one or more layers selected from the group consisting of: a hole injection layer; a hole transport layer; a hole injection and transport layer; an electron injection layer; an electron transport layer; and an electron injection and transport layer.
15. A method for manufacturing an organic light emitting device, the method comprising:
preparing a first electrode;
forming an organic material layer having one or more layers on the first electrode; and
forming a second electrode on the organic material layer having one or more layers,
wherein the forming an organic material layer having one or more layers comprises forming the organic material layer by a solution method using the coating composition according to any one of claims 1 to 12.
16. The method of claim 15, wherein forming the organic material layer using the coating composition comprises:
coating the coating composition on the first electrode or the organic material layer having one or more layers; and
the applied coating composition is dried, heat treated or light treated.
17. The method of claim 16, wherein the heat treatment temperature of the heat treatment step is 80 ℃ to 250 ℃.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2022-0006600 | 2022-01-17 | ||
| KR10-2022-0006603 | 2022-01-17 | ||
| KR20220006603 | 2022-01-17 | ||
| PCT/KR2023/000803 WO2023136707A1 (en) | 2022-01-17 | 2023-01-17 | Coating composition, organic light-emitting device comprising same, and manufacturing method therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117796180A true CN117796180A (en) | 2024-03-29 |
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| CN202380013156.0A Pending CN117796180A (en) | 2022-01-17 | 2023-01-17 | Coating composition, organic light emitting device including the same, and method of manufacturing the same |
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| Country | Link |
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