CN114174286B - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN114174286B CN114174286B CN202080052532.3A CN202080052532A CN114174286B CN 114174286 B CN114174286 B CN 114174286B CN 202080052532 A CN202080052532 A CN 202080052532A CN 114174286 B CN114174286 B CN 114174286B
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 11
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- 239000001257 hydrogen Substances 0.000 claims description 10
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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Abstract
The present invention relates to a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0130847 at 10 months 21 in 2019 and korean patent application No. 10-2020-0130179 at 10 months 12 in 2020, the entire contents of the disclosures of the korean patent application are incorporated as part of the present specification.
The present invention relates to a novel compound and an organic light emitting device using the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2013-073537
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 3 Each independently is N or CH, but X 1 To X 3 More than one of them isN，
L 1 To L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is hydrogen; deuterium; adamantyl; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 7-60 An arylalkyl group; substituted or unsubstituted C 7-60 An arylalkenyl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroaryl, but Ar 1 And Ar is a group 2 More than one of them is adamantyl,
R 1 and R is 2 Is hydrogen, deuterium, or substituted or unsubstituted C 1-60 An alkyl group, a hydroxyl group,
m is an integer of 0 to 7,
n is an integer from 0 to 8.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound of the present invention.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material of the hole blocking layer.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 4, a hole blocking layer 9, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
(description of the words)
In the present description of the invention,represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium (D); a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkyl thioxy [ ]Alkylthio) is described; aryl thioxy (+)>Aryl thio xy); alkylsulfonyl (+)>Alkylsulfoxy); arylsulfonyl (+)>Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in a heterocyclic group comprising 1 or more of S atoms, or a substituent which is bonded to 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the group may be a group of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon atoms of the aryl groups mentioned aboveThe number is 6 to 30. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be thatEtc. However, the present invention is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as exemplified for the aryl group described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied thereto. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
(Compound)
The present invention provides a compound represented by the above chemical formula 1. The compound represented by chemical formula 1 is a compound in which a triazine substituent (including pyridine, pyrimidine, and triazine) is bonded to a core structure formed by spiro bonding of xanthene and fluorene, and has an adamantyl (amantayl) group as one of the additional substituents of the triazine substituent. Such compounds may exhibit improved hole-electron bonding and improved thermal stability compared to compounds substituted with triazine-based substituents having no adamantyl groups. Therefore, the organic light emitting device using the above compound can exhibit characteristics of high efficiency, low driving voltage, long life, and the like.
The compound represented by chemical formula 1 is specifically shown below:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 3 Each independently is N or CH, but X 1 To X 3 More than one of them is N,
L 1 to L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is hydrogen; deuterium; adamantyl; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 7-60 An arylalkyl group; substituted or unsubstituted C 7-60 An arylalkenyl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroaryl, but Ar 1 And Ar is a group 2 More than one of them is adamantyl,
R 1 and R is 2 Is hydrogen, deuterium, or substituted or unsubstituted C 1-60 An alkyl group, a hydroxyl group,
m is an integer of 0 to 7,
n is an integer from 0 to 8.
Preferably, the compound represented by the above chemical formula 1 is a compound represented by the following chemical formulas 1-1 to 1-3:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3,
X 1 、X 2 、X 3 、L 1 、L 2 、L 3 、Ar 1 、Ar 2 、R 1 、R 2 m and n are as defined above.
Preferably L 1 To L 3 Each independently is a single bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, a terphenylene group substituted or unsubstituted with deuterium, a fluorenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.
In addition, preferably L 1 To L 3 Each independently is a single bond, phenylene, biphenylene, or naphthylene.
Preferably Ar 1 And Ar is a group 2 Each independently is deuterium, adamantyl, or any one selected from the following groups, but Ar 1 And Ar is a group 2 More than one of them is adamantyl:
of the above-mentioned groups, the group,
x is O, S or NR, and the like,
r is substituted or unsubstituted C 6-12 An aryl group,
R' 1 and R'. 2 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-12 Aryl groups.
Preferably, R is phenyl.
Preferably, R' 1 And R'. 2 Each independently is methyl.
Preferably, R 1 And R is 2 Each independently is hydrogen or deuterium.
Preferably, m and n are each independently 0 or 1.
Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following compounds:
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the compound represented by the above chemical formula 1 can be produced by the following reaction formula 1.
[ reaction type 1]
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In the above reaction formula 1, the definition of substituents other than X is the same as that described above, and X is halogen, preferably bromine or chlorine.
The reaction formula 1 is a suzuki coupling reaction, preferably in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be modified according to techniques known in the art.
In the compound represented by the above chemical formula 1, the position of each substituent can be manufactured by referring to the above reaction formula 1 and by appropriately changing the structure of the starting material. The method for producing the compound represented by the above chemical formula 1 can be more specifically described in the production examples described later.
(organic light-emitting device)
In another aspect, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
The organic layer may include a hole blocking layer including a compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
The organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate in a reverse structure (inverted type). For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 4, a hole blocking layer 9, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole blocking layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole blocking layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode is an anode, and the second electrode is a cathode; or the first electrode is a cathode, and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include magnesium and calciumMetals such as sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and as a hole injection substance, the following compounds are preferable: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. As the hole transporting substance, a compound represented by the above chemical formula 1, an arylamine-based organic substance, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, or the like can be used, but the present invention is not limited thereto.
The electron suppression layer (or electron blocking layer) refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and improving the probability of hole-electron bonding. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, a compound represented by the above chemical formula 1, an organic compound of an arylamine group, or the like can be used, but the present invention is not limited thereto.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material as described above. The host material may also include aromatic fused ring derivatives or heterocyclic containing compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene and the like, a styrylamine compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, is selected from 1 or 2 or more of aryl, silyl, alkyl, cycloalkyl and arylamino groupsThe substituents on the ring are substituted or unsubstituted. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The hole blocking layer (or hole suppressing layer) refers to the following layer: the organic light-emitting layer is preferably formed on the light-emitting layer, and is preferably provided in contact with the light-emitting layer, and serves to improve the efficiency of the organic light-emitting layer device by adjusting the electron mobility, thereby preventing excessive migration of holes and improving the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance, and the compound represented by chemical formula 1 of the present invention can be used. In addition, as examples of the hole blocking substance that can be used additionally, azine derivatives including triazines, triazole derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from an electrode and transports the received electrons to a light emitting layer and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high electron mobility. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) with (c), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazole, triazole,Imidazole, perylene tetracarboxylic acid, fluorenylene methane, anthrone, and the like are used together with their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
The electron injection and transport layer may be formed as separate layers such as an electron injection layer and an electron transport layer. In this case, an electron transporting layer is formed over the light emitting layer or the hole blocking layer, and the electron injecting and transporting substance can be used as the electron transporting substance contained in the electron transporting layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, naCl, csF, li can be used as an electron injection material contained in the electron injection layer 2 O, baO fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Production example a: synthesis of intermediate compound A
2-bromobiphenyl (8.72 g,37.44 mmol) as compound y-1 was dissolved in 35ml of THF in a 500ml round-bottomed flask under nitrogen atmosphere, cooled to-78℃and then 4.77ml (2.5M pentane solution) of t-butyllithium (t-BuLi) was added dropwise thereto, followed by stirring at the same temperature for 40 minutes. After 2-bromo-9H-xanthen-9-one (9.36 g,34.04 mmol) was added as compound x-1 to the prepared solution, the temperature was slowly raised to room temperature and stirred for 3 hours. Then, the above-mentioned reaction product was poured into a mixed solution of 15ml of diethyl ether and 25ml of a 2N aqueous hydrochloric acid solution, and then stirred for 30 minutes, and the resultant solid was filtered, washed with water and diethyl ether, and then dried. After 2.5g of acetic acid dissolved in 50ml of the above-mentioned dried solid sample was taken, a catalyst amount (10 drops) of concentrated sulfuric acid was added thereto and refluxed for 3 hours. Then, the resultant solid compound was filtered, washed with acetic acid and dried to obtain compound a-1 (9.75 g, yield: 70%) as a white solid compound.
Then, under a nitrogen atmosphere, the compound of formula A-1 (9.75 g,23.72 mmol) and pinacol diboron (7.91 g,30.85 mmol), potassium acetate (6.98 g,71.17 mmol) were mixed and added to the mixtureThe alkane (240 ml) was heated with stirring. Bis (dibenzylideneacetone) palladium (0.36 g,0.71 mmol) and tricyclohexylphosphine (0.35 g,1.42 mmol) were added under reflux, heated and stirred for 12 hours. After the reaction, the temperature was lowered to room temperature and then filtered. Water was then added to the filtrate, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed, whereby intermediate compound A (7.74 g, yield: 71%) was obtained.
MS[M+H] + ＝458
Production example B: synthesis of intermediate compound B
In production example A, an intermediate compound B was produced in the same manner as in production example A except that the starting material x-2 was used instead of the starting material x-1.
MS[M+H] + ＝458
Production example C: synthesis of intermediate compound C
In production example A, an intermediate compound C was produced in the same manner as in production example A except that the starting material x-3 was used instead of the starting material x-1.
MS[M+H] + ＝458
Production example 1: synthesis of Compound 1
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After compound A (9.39 g,20.50 mmol) and a-1 (7.49 g,18.63 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round-bottomed flask under a nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.65 g,0.56 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 260ml of tetrahydrofuran, whereby compound 1 (9.11 g, 70%) was produced.
MS[M+H] + ＝698
Production example 2: synthesis of Compound 2
After compound A (6.64 g,14.50 mmol) and compound a-2 (6.88 g,13.18 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was added, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 310ml of ethyl acetate, whereby compound 2 (7.63 g, 75%) was produced.
MS[M+H] + ＝774
Production example 3: synthesis of Compound 3
After compound B (7.13 g,15.57 mmol) and compound B-1 (7.05 g,14.16 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.49 g,0.42 mmol) was added, followed by stirring with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 290ml of tetrahydrofuran, whereby compound 3 (6.88 g, 65%) was produced.
MS[M+H] + ＝748
Production example 4: synthesis of Compound 4
After compound B (6.96 g,15.21 mmol) and compound B-2 (7.23 g,13.82 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.48 g,0.41 mmol) was added, followed by stirring with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 320ml of tetrahydrofuran, whereby compound 4 (7.94 g, 74%) was produced.
MS[M+H] + ＝773
Production example 5: synthesis of Compound 5
After compound C (7.18 g,15.68 mmol) and compound C-1 (7.67 g,14.26 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.49 g,0.43 mmol) was added, followed by stirring with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 240ml of tetrahydrofuran, whereby compound 5 (6.09 g, 54%) was produced.
MS[M+H] + ＝788
Production example 6: synthesis of Compound 6
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After compound B (5.70 g,12.44 mmol) and compound c-2 (6.55 g,11.31 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.39 g,0.34 mmol) was added, followed by stirring with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 250ml of ethyl acetate, whereby compound 6 (7.11 g, 75%) was produced.
MS[M+H] + ＝833
Production example 7: synthesis of Compound 7
After compound A (6.28 g,13.72 mmol) and a-3 (6.87 g,12.47 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round-bottomed flask under a nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 270ml of tetrahydrofuran, whereby compound 7 (6.61 g, 66%) was produced.
MS[M+H] + ＝805
Production example 8: synthesis of Compound 8
After compound A (6.28 g,13.71 mmol) and a-4 (7.28 g,12.47 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 280ml of tetrahydrofuran, whereby compound 8 (5.77 g, 63%) was produced.
MS[M+H] + ＝738
Production example 9: synthesis of Compound 9
After compound B (6.26 g,13.67 mmol) and compound B-3 (6.66 g,12.43 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added, followed by stirring with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 280ml of tetrahydrofuran, whereby compound 9 (6.49 g, 63%) was produced.
MS[M+H] + ＝833
Production example 10: synthesis of Compound 10
After compound C (10.65 g,23.25 mmol) and compound C-3 (8.16 g,21.14 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.73 g,0.63 mmol) was added, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 280ml of ethyl acetate, whereby compound 10 (7.16 g, 50%) was produced.
MS[M+H] + ＝680
Production example 11: synthesis of Compound 11
After compound C (4.96 g,10.83 mmol) and compound C-4 (5.89 g,9.85 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.34 g,0.30 mmol) was added, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 280ml of tetrahydrofuran, whereby compound 11 (6.95 g, 50%) was produced.
MS[M+H] + ＝909
Production example 12: synthesis of Compound 12
After compound C (5.55 g,12.12 mmol) and compound C-5 (5.74 g,11.02 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.38 g,0.33 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 250ml of tetrahydrofuran, whereby compound 12 (6.54 g, 77%) was produced.
MS[M+H] + ＝773
Production example 13: synthesis of Compound 13
After compound C (6.44 g,14.06 mmol) and compound C-6 (6.66 g,12.78 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol) was added, followed by stirring with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 240ml of tetrahydrofuran, whereby compound 13 (5.84 g, 59%) was produced.
MS[M+H] + ＝774
Example 1-1: fabrication of organic light emitting devices
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>The EB1 compound was vacuum-evaporated to form an electron-inhibiting layer. Next, on the above electron suppression layer, the film thickness is +.>A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. On the above-mentioned light-emitting layer, the film thickness is +.>The compound represented by compound 1 synthesized in production example 1 was subjected to vacuum evaporation to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form ∈ ->Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>To the thickness of aluminumAnd the thickness of the metal layer is evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain the vacuum degree at 2X10 during vapor deposition -7 ～5X10 -6 The support is thus fabricated into an organic light emitting device.
Examples 1-2 to 1-13 and comparative examples 1-1 to 1-3
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the hole blocking layer was formed using the compound described in table 1 below instead of the compound of manufacturing example 1. The compounds of HB1, HB2 and HB3 used in Table 1 below are shown below.
Experimental example
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device using the compound of the present invention as a hole blocking layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.
In examples 1-1 to 1-13, the organic light-emitting device using the compound of the present invention exhibited characteristics of low voltage, high efficiency, and long lifetime as compared with the organic light-emitting devices of comparative examples 1-1, 1-2, and 1-3 produced using a material in which the core structure formed by the spiro bonding of xanthene and fluorene is not substituted with a triazine group containing one or more adamantyl groups, HB1, HB2, and HB 3.
[ description of the symbols ]
1: substrate 2: anode
3: hole transport layer 4: light-emitting layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: electron suppression layer
9: a hole blocking layer.
Claims (8)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
X 1 to X 3 Each independently is N or CH, but X 1 To X 3 More than one of them is N,
L 1 to L 3 Each independently is a single bond, or C substituted or unsubstituted with deuterium 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is hydrogen, deuterium, adamantyl, or any one selected from the following groups, but Ar 1 And Ar is a group 2 More than one of them is adamantyl:
among the groups of the radicals in which the radicals are formed,
x is O or S, and the X is O or S,
R' 1 and R'. 2 Each independently is hydrogen, deuterium, C 1-10 Alkyl, or C 6-12 An aryl group,
R 1 and R is 2 Is hydrogen, deuterium, or C 1-60 An alkyl group, a hydroxyl group,
m is an integer of 0 to 7,
n is an integer from 0 to 8.
2. The compound according to claim 1, wherein the compound represented by chemical formula 1 is represented by the following chemical formulas 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
In the chemical formulas 1-1 to 1-3,
X 1 、X 2 、X 3 、L 1 、L 2 、L 3 、Ar 1 、Ar 2 、R 1 、R 2 m and n are as defined in claim 1.
3. The compound of claim 1, wherein L 1 To L 3 Each independently is a single bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, a terphenylene group substituted or unsubstituted with deuterium, a fluorenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.
4. The compound according to claim 1, wherein，L 1 To L 3 Each independently is a single bond, phenylene, biphenylene, or naphthylene.
5. The compound of claim 1, wherein R 1 And R is 2 Each independently is hydrogen or deuterium.
6. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
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7. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 6.
8. The organic light-emitting device according to claim 7, wherein the organic layer containing the compound is a hole blocking layer.
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| KR1020200131019A KR102486519B1 (en) | 2019-10-21 | 2020-10-12 | Novel compound and organic light emitting device comprising the same |
| PCT/KR2020/014150 WO2021080253A1 (en) | 2019-10-21 | 2020-10-16 | Novel compound and organic light emitting device comprising same |
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| CN112876462B (en) * | 2020-05-12 | 2022-01-21 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
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| KR20180069423A (en) * | 2016-12-15 | 2018-06-25 | (주)씨엠디엘 | Spirofluorenexanthenyl derivatives and organic electroluminescent device including the same |
| CN108290854A (en) * | 2016-02-23 | 2018-07-17 | 株式会社Lg化学 | Heterocyclic compound and organic luminescent device comprising it |
| TW201843148A (en) * | 2017-05-08 | 2018-12-16 | 國立大學法人京都大學 | Compound, light emitting material and organic light emitting element |
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| KR20190101739A (en) * | 2018-02-23 | 2019-09-02 | 주식회사 엘지화학 | Organic light emitting device |
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| CN108290854A (en) * | 2016-02-23 | 2018-07-17 | 株式会社Lg化学 | Heterocyclic compound and organic luminescent device comprising it |
| KR20180069423A (en) * | 2016-12-15 | 2018-06-25 | (주)씨엠디엘 | Spirofluorenexanthenyl derivatives and organic electroluminescent device including the same |
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