CN112533912A - Compound and organic light emitting device including the same - Google Patents
Compound and organic light emitting device including the same Download PDFInfo
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- CN112533912A CN112533912A CN201980051801.1A CN201980051801A CN112533912A CN 112533912 A CN112533912 A CN 112533912A CN 201980051801 A CN201980051801 A CN 201980051801A CN 112533912 A CN112533912 A CN 112533912A
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
- 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-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
- 239000011541 reaction mixture Substances 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [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
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application relates to a compound and an organic light emitting device including the same.
The present application claims priority of korean patent application No. 10-2018-.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure of a first electrode and a second electrode with an organic layer included therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the first electrode into the organic layer, electrons are injected from the second electrode into the organic layer, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
Disclosure of Invention
Technical subject
Provided are a compound and an organic light emitting device including the same.
Means for solving the problems
The present application provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
X1 is NR, X2 is a direct bond; or X1 is a direct bond, X2 is NR,
a is benzene, and the content of A is,
r is represented by the following chemical formula 2,
[ chemical formula 2]
L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar is any one selected from the following structural formulas,
r' is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
x is an integer of 0 to 5,
y is an integer of 0 to 7,
when x or y is 2 or more, the substituents in parentheses may be the same or different from each other,
a is 1 or 2, and a is,
when a is 2, the substituents in parentheses may be the same or different from each other.
In addition, the present application provides an organic light emitting device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face 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 contain the compound.
Effects of the invention
An organic light emitting device using the compound according to an embodiment of the present application can achieve a low driving voltage, high light emitting efficiency, or a long lifetime.
Drawings
Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked.
Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a second electrode 4 are sequentially stacked.
Fig. 3 illustrates an example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked.
[ description of symbols ]
1: substrate
2: a first electrode
3: luminescent layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron blocking layer
9: hole blocking layer
10: electron injection and transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the above chemical formula 1.
According to an embodiment of the present application, the compound represented by the above chemical formula 1 has an advantage in that triplet energy can be adjusted by having the core structure as described above, and can exhibit characteristics of a long life and high efficiency.
In the present specification, examples of the substituent are described below, but not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from the group consisting of hydrogen, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like, but is not limited thereto.
In the present specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e. heteroatomsSpecifically, the heteroatom may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms of the heteroaryl group is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Azolyl group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the above description about aryl groups can be applied to arylene groups other than those having a valence of 2.
In this specification, the above description on heteroaryl groups can be applied except that heteroarylene groups are 2-valent groups.
According to an embodiment of the present application, X1 is NR and X2 is a direct bond; or X1 is a direct bond and X2 is NR. That is, instead of both X1 and X2 being directly bonded or both X1 and X2 being NR, one of X1 and X2 is directly bonded and the remaining one is NR.
According to an embodiment of the present application, a is a benzene ring.
According to an embodiment of the present application, R is represented by the following chemical formula 2.
[ chemical formula 2]
According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.
According to an embodiment of the present application, L is a direct bond, 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 embodiment of the present application, L is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 15 carbon atoms.
According to an embodiment of the present application, L is a directly bonded arylene group having 6 to 20 carbon atoms which may be substituted with an aryl group having 6 to 20 carbon atoms or unsubstituted.
According to an embodiment of the present application, the above L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
According to an embodiment of the present application, L is a direct bond, a phenylene group substituted or unsubstituted with an aryl group, a naphthylene group substituted or unsubstituted with an aryl group, or a biphenylene group substituted or unsubstituted with an aryl group.
According to an embodiment of the present application, L is a direct bond, a phenylene group substituted or unsubstituted with a phenyl group, a naphthylene group substituted or unsubstituted with a phenyl group, or a biphenylene group substituted or unsubstituted with a phenyl group.
According to an embodiment of the present application, Ar is any one selected from the following structural formulae.
According to an embodiment of the present application, R' as described above is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.
According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.
According to an embodiment of the present application, R' is hydrogen; deuterium; aryl substituted or unsubstituted with deuterium, alkyl or aryl; or heteroaryl substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, R' is hydrogen; deuterium; aryl substituted or unsubstituted with deuterium, alkyl or aryl; or a tricyclic heteroaryl group substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
According to an embodiment of the present application, the "substituted or unsubstituted" of R' means substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, and an aryl group.
According to an embodiment of the present application, the "substituted or unsubstituted" of R' means substituted or unsubstituted with 1 or more substituents selected from deuterium, methyl, and phenyl.
According to an embodiment of the present application, R' is hydrogen; deuterium; phenyl unsubstituted or substituted by deuterium, alkyl or aryl; naphthyl substituted or unsubstituted with deuterium, alkyl or aryl; biphenyl substituted or unsubstituted with deuterium, alkyl or aryl; terphenyl optionally substituted with deuterium, alkyl or aryl; phenanthryl substituted or unsubstituted with deuterium, alkyl or aryl; fluorenyl substituted or unsubstituted with deuterium, alkyl or aryl; triphenylene substituted or unsubstituted with deuterium, alkyl, or aryl; dibenzofuranyl substituted or unsubstituted with deuterium, alkyl or aryl; dibenzothienyl substituted or unsubstituted with deuterium, alkyl or aryl; or carbazolyl substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, R' is hydrogen; deuterium; phenyl unsubstituted or substituted by deuterium, alkyl or aryl; naphthyl substituted or unsubstituted with deuterium, alkyl or aryl; biphenyl substituted or unsubstituted with deuterium, alkyl or aryl; terphenyl optionally substituted with deuterium, alkyl or aryl; phenanthryl substituted or unsubstituted with deuterium, alkyl or aryl; fluorenyl substituted or unsubstituted with deuterium, alkyl or aryl; triphenylene substituted or unsubstituted with deuterium, alkyl, or aryl; a dibenzofuranyl group; a dibenzothienyl group; or carbazolyl substituted or unsubstituted with aryl.
According to an embodiment of the present application, R' is hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, methyl or phenyl; naphthyl substituted or unsubstituted by deuterium, methyl or phenyl; biphenyl substituted or unsubstituted with deuterium, methyl or phenyl; terphenyl optionally substituted with deuterium, methyl or phenyl; phenanthryl substituted or unsubstituted with deuterium, methyl or phenyl; fluorenyl substituted or unsubstituted with deuterium, methyl or phenyl; triphenylene substituted or unsubstituted with deuterium, methyl, or phenyl; a dibenzofuranyl group; a dibenzothienyl group; or carbazolyl substituted or unsubstituted with phenyl.
According to an embodiment of the present application, R' is hydrogen, deuterium, a phenyl group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium or a phenyl group, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group substituted or unsubstituted by deuterium, a phenanthryl group substituted or unsubstituted by deuterium, a fluorenyl group substituted or unsubstituted by a methyl group or a phenyl group, a triphenylene group substituted or unsubstituted by deuterium, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted by phenyl.
According to an embodiment of the present application, when x is an integer of 0 to 5, y is an integer of 0 to 7, and x or y is 2 or more, the substituents in the parentheses are the same or different from each other.
According to an embodiment of the present application, x and y are 1.
According to an embodiment of the present application, when a is 1 or 2 and a is 2, the substituents in parentheses may be the same or different from each other.
According to an embodiment of the present application, Ar is any one selected from the following structural formulae.
In the above structural formula, R' is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
x1 is an integer from 0 to 4,
y1 is an integer from 0 to 6,
when x or y is 2 or more, the substituents in parentheses may be the same or different from each other,
ra is a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.
According to an embodiment of the present application, R "is hydrogen or deuterium.
According to an embodiment of the present application, Ra is aryl substituted or unsubstituted with deuterium, alkyl or aryl; or heteroaryl substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, Ra is aryl substituted or unsubstituted with deuterium, alkyl or aryl; or a tricyclic heteroaryl group substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, Ra is hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
According to an embodiment of the present application, the "substituted or unsubstituted" for Ra means substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, and an aryl group.
According to an embodiment of the present application, the "substituted or unsubstituted" for Ra means substituted or unsubstituted with 1 or more substituents selected from deuterium, methyl, and phenyl.
According to an embodiment of the present application, Ra is phenyl substituted or unsubstituted with deuterium, alkyl or aryl; naphthyl substituted or unsubstituted with deuterium, alkyl or aryl; biphenyl substituted or unsubstituted with deuterium, alkyl or aryl; terphenyl optionally substituted with deuterium, alkyl or aryl; phenanthryl substituted or unsubstituted with deuterium, alkyl or aryl; fluorenyl substituted or unsubstituted with deuterium, alkyl or aryl; triphenylene substituted or unsubstituted with deuterium, alkyl, or aryl; dibenzofuranyl substituted or unsubstituted with deuterium, alkyl or aryl; dibenzothienyl substituted or unsubstituted with deuterium, alkyl or aryl; or carbazolyl substituted or unsubstituted with deuterium, alkyl or aryl.
According to an embodiment of the present application, Ra is deuterium; phenyl unsubstituted or substituted by deuterium, alkyl or aryl; naphthyl substituted or unsubstituted with deuterium, alkyl or aryl; biphenyl substituted or unsubstituted with deuterium, alkyl or aryl; terphenyl optionally substituted with deuterium, alkyl or aryl; phenanthryl substituted or unsubstituted with deuterium, alkyl or aryl; fluorenyl substituted or unsubstituted with deuterium, alkyl or aryl; triphenylene substituted or unsubstituted with deuterium, alkyl, or aryl; a dibenzofuranyl group; a dibenzothienyl group; or carbazolyl substituted or unsubstituted with aryl.
According to an embodiment of the present application, Ra is phenyl substituted or unsubstituted with deuterium, methyl or phenyl; naphthyl substituted or unsubstituted by deuterium, methyl or phenyl; biphenyl substituted or unsubstituted with deuterium, methyl or phenyl; terphenyl optionally substituted with deuterium, methyl or phenyl; phenanthryl substituted or unsubstituted with deuterium, methyl or phenyl; fluorenyl substituted or unsubstituted with deuterium, methyl or phenyl; triphenylene substituted or unsubstituted with deuterium, methyl, or phenyl; a dibenzofuranyl group; a dibenzothienyl group; or carbazolyl substituted or unsubstituted with phenyl.
According to an embodiment of the present application, Ra is a phenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium or a phenyl group, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group substituted or unsubstituted with deuterium, a phenanthryl group substituted or unsubstituted with deuterium, a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group, a triphenylene group substituted or unsubstituted with deuterium, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted with phenyl group.
According to an embodiment of the present application, Ar is selected from any one of the following structural formulae.
Ra in the above structural formula is the same as defined above.
According to an embodiment of the present application, the chemical formula 1 is represented by the following chemical formula 1-1.
[ chemical formula 1-1]
In the above chemical formula 1-1,
r is as defined above.
According to an embodiment of the present application, the chemical formula 1 is represented by the following chemical formula 1-2.
[ chemical formulas 1-2]
In the above chemical formula 1-2,
r is as defined above.
In addition, according to an embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following structural formulae.
In addition, the present specification provides an organic light emitting device comprising the above-mentioned compound.
In one embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face 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 contain the compound.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
The organic layer of the organic light-emitting device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In one embodiment of the present disclosure, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
In one embodiment of the present specification, the compound is included as a host of the light-emitting layer.
In one embodiment of the present specification, the compound is included as a red host of the light-emitting layer.
In one embodiment of the present disclosure, the light-emitting layer further includes a dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a main component, and may include an iridium-based dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include a phosphorescent dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include a red or green phosphorescent dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include an iridium-based phosphorescent dopant.
According to one embodiment of the present specification, the light-emitting layer includes the compound and a dopant in a weight ratio of 1:99 to 99: 1.
According to one embodiment of the present specification, the light-emitting layer includes the compound and a dopant in a weight ratio of 2:1 to 99: 1.
In one embodiment of the present specification, the iridium-based dopant may be selected from the following structures, but is not limited thereto.
In one embodiment of the present disclosure, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
In one embodiment of the present disclosure, the organic layer may include a hole injection layer, a hole transport layer, or an electron blocking layer.
In one embodiment of the present specification, the organic layer may include a hole injection layer, a hole transport layer, and an electron blocking layer.
In one embodiment of the present specification, the organic layer may include a hole blocking layer or an electron injection and transport layer.
In one embodiment of the present specification, the organic layer may include a hole blocking layer, and an electron injection and transport layer.
In one embodiment of the present specification, the organic light emitting device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, and a hole blocking layer.
In one embodiment of the present application, the organic light emitting device includes: a first electrode; a second electrode provided to face the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and 2 or more organic layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the 2 or more organic layers contains the compound. In one embodiment of the present application, the 2 or more organic layers may be 2 or more layers selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.
In one embodiment of the present application, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be contained in 1 of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.
In one embodiment of the present application, when the compound is contained in each of the electron transport layers having 2 or more layers, materials other than the compound may be the same as or different from each other.
In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.
In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which a first electrode, 1 or more organic layers, and a second electrode are sequentially stacked on a substrate.
In another embodiment, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a second electrode, 1 or more organic layers, and a first electrode are sequentially stacked on a substrate.
For example, fig. 1 and 2 show examples of the structure of an organic light emitting device according to an embodiment of the present specification.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked. In such a structure, the above compound may be contained in the above light-emitting layer 3.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a second electrode 4 are sequentially stacked. In such a structure, the compound may be contained in 1 or more of the hole injection layer 5, the hole transport layer 6, the light-emitting layer 3, and the electron transport layer 7.
Fig. 3 illustrates a structure of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked, and the above compound may be included in the light emitting layer 3, but is not limited thereto.
In the structure as described above, the above compound may be contained in 1 or more of the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.
The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that 1 or more of the organic layers contain the compound of the present specification, i.e., the above compound.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above compound, i.e., the compound represented by the above chemical formula 1.
For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by forming a first electrode by depositing metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the first electrode, and then depositing a substance which can be used as a second electrode on the organic layer. In addition to this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light-emitting device.
In addition, the compound of chemical formula 1 may be used to form an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, a second electrode material, an organic layer, and a first electrode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device (international patent application publication No. 2003/012890). However, the production method is not limited thereto.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is an anode.
The first electrode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the first electrode material that can be used in the present invention 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); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The second electrode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the second electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection material is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection material: a compound having an ability to transport holes, having an effect of injecting holes from the first electrode, having an excellent hole injection effect for the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the electron-injecting layer or the electron-injecting material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the first electrode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
In one embodiment of the present application, the organic layer includes a hole injection layer, and the hole injection layer is p-doped.
In one embodiment of the present application, the organic layer includes a hole injection layer, and the hole injection layer is p-doped.
In one embodiment of the present specification, the hole injection layer further includes a p-dopant.
In the present specification, the p-doped substance refers to a substance that imparts p-semiconductor characteristics to the host substance. The p-semiconductor property refers to a property of injecting or transporting holes at a HOMO (highest occupied molecular orbital) level, that is, a property of a substance having a large hole conductivity. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the first electrode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably fluorescentA substance having high quantum efficiency of light or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compound
Pyrimidine derivatives, etc., but are not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can be injected and received from the second electrode well and transferred to the light emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer isThe layer for injecting electrons from the electrode is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from the second electrode, having an excellent electron injection effect for the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, 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 hole blocking layer is a layer that prevents holes from reaching the second electrode, and can be formed under the same conditions as those of the hole injection layer. Specifically, there are
An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
The method for producing the compound of chemical formula 1 and the production of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
The compound of the present invention is produced by using, as typical reactions, a Buchwald-Hartwig coupling reaction (Buchwald-Hartwig coupling reaction), Suzuki coupling reaction (Suzuki coupling reaction), Heck coupling reaction (Heck coupling reaction), and the like.
Production example 1.
After 100.0g (1.0 equivalent) of 1-bromotriphenylene and 60.04g (1.1 equivalent) of (2-nitrophenyl) boronic acid were dissolved in 1000ml of Tetrahydrofuran (THF), 90.33g (2.0 equivalent) of K was added2CO3Dissolved in 300ml of water and added together. 1.59g (0.005 eq) of Pd (t-Bu) were added3P)2Refluxing and stirring. At the end of the reaction, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3And washed with water, treated with anhydrous magnesium sulfate and removed the solvent again under reduced pressure, which was subjected to column chromatography, to obtain compound a-184.42 g, yield 74%). [ M + H ]]+＝350
84.42g (1.0 eq) of formula A-1 was added to 200mL of triethyl phosphite, refluxed and stirred. After 2 hours the reaction was complete, the reaction was poured into 2L of ethanol and the solids were allowed to fall. The solid was completely dissolved in CHCl3Thereafter, the reaction mixture was washed with water, treated with anhydrous magnesium sulfate, and the solution was concentrated under reduced pressure and purified by column chromatography. Compound A48.31 g was obtained in 63% yield. [ M + H ]]+＝318
Production example 2.
100.0g (1.0 equivalent) of 2-chloroaniline, 240.9g (1.1 equivalent) of 1-bromotriphenyleneAfter dissolving in 1000ml of toluene, 151.33g (2.0 equivalents) of NaOtBu were added together. 4.02g (0.01 eq) of Pd (t-Bu) were added3P)2Refluxing and stirring. At the end of the reaction, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3And washed with water, treated with anhydrous magnesium sulfate and removed the solvent again under reduced pressure, which was subjected to column chromatography, to obtain compound B-1205.71 g, yield 74%). [ M + H ]]+＝354
205.0g (1.0 equivalent) of Compound B-1 was dissolved in 1000mL of dimethylacetamide (DMAc), and 247.33g (2.0 equivalents) of K was added3PO42.97g (0.01 eq.) of Pd (t-Bu)3P)2Refluxing and stirring. After the reaction, the mixture was cooled, poured into water, stirred and solidified, and then filtered. Then, completely dissolved in CHCl3And washed with water, treated with anhydrous magnesium sulfate and removed the solvent again under reduced pressure, which was subjected to column chromatography, to obtain compound B136.7 g, yield 74%). [ M + H ]]+＝318
< Synthesis example >
Synthesis example 1
10.0g (1.0 equiv) of Compound A, 12.90g (1.1 equiv) of 3- ([1,1' -Biphenyl)]-4-yl) -2-chloro-benzene [4,5]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 1(15.03g, yield 73%). [ M + H ]]+＝654
Synthesis example 2
10.0g (1.0 equivalent) of Compound A, 15.99g (1.1 equivalent) of 3-chloro-2- (9-phenyl-9H-carbazol-2-yl) benzo [4,5 ]]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 2(16.38g, yield 70%). [ M + H ]]+＝743
Synthesis example 3
10.0g (1.0 equivalent) of Compound A, 12.80g (1.1 equivalent) of 2- (9H-carbazol-9-yl) -3-chlorobenzofurano [2,3-b]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 3(13.12g, yield 64%). [ M + H ]]+＝651
Synthesis example 4
10.0g (1.0 equiv) of Compound A, 13.25g (1.1 equiv) of 3- ([1,1' -Biphenyl)]-3-yl) -2-chloro-9, 9-dimethyl-9H-indeno [1,2-b]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 min)Amount) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 4(12.45g, yield 61%). [ M + H ]]+＝664
Synthesis example 5
10.0g (1.0 eq) of Compound A, 16.34g (1.1 eq) of 2-chloro-9, 9-dimethyl-3- (9-phenyl-9H-carbazol-4-yl) -9H-indeno [1,2-b]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 5(14.94g, yield 63%). [ M + H ]]+＝753
Synthesis example 6
10.0g (1.0 equivalent) of Compound A, 13.73g (1.1 equivalent) of 2-chloro-4- (dibenzo [ b, d ] are added]Thien-1-yl) benzo [ h]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Adding ethyl acetate again under reflux to reduce crystalsAnd (4) cooling and filtering. This was subjected to column chromatography to give compound 6(13.02g, yield 61%). [ M + H ]]+＝678
Synthesis example 7
10.0g (1.0 equivalent) of Compound A, 13.53g (1.1 equivalent) of 3-chloro-1- (phenanthren-2-yl) benzo [ f]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g of K3PO4(2.0 equiv.) to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 7(13.75g, yield 65%). [ M + H ]]+＝672
Synthesis example 8
10.0g (1.0 equiv) of Compound A, 15.33g (1.1 equiv) of 3- ([1,1':3', 1' -terphenyl]-5' -yl) -1-chlorobenzo [ f]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 8(13.91g, yield 61%). [ M + H ]]+＝724
Synthesis example 9
10.0g (1.0 equivalent) of Compound A, 11.79g (1.1 equivalent) of 2-chloro-3- (naphthalen-1-yl) benzo [ f]Quinoxaline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. Column chromatography was performed thereon to obtain compound 9(13.12g, yield 67%). [ M + H ]]+＝622
Synthesis example 10
10.0g (1.0 equiv.) of Compound A, 15.33g (1.1 equiv.) of 2- ([1,1':4', 1' -terphenyl]-4-yl) -3-chlorobenzo [ f]Quinoxaline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 10(14.14g, yield 62%). [ M + H ]]+＝724
Synthesis example 11
10.0g (1.0 equivalent) of Compound A, 12.69g (1.1 equivalent) of 2-chloro-3- (4-phenylnaphthalen-1-yl) quinoxaline, 0.16g (0.01 equivalent) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. 2 smallAfter the reaction, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 11(13.87g, yield 68%). [ M + H ]]+＝648
Synthesis example 12
10.0g (1.0 equiv) of Compound A, 19.70g (1.1 equiv) of 2- ([1,1' -Biphenyl)]-4-yl) -3- (3 '-bromo- [1,1' -biphenyl]-4-yl) benzo [4,5]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 12(18.02g, yield 71%). [ M + H ]]+＝806
Synthesis example 13
10.0g (1.0 equiv.) of Compound A, 17.55g (1.1 equiv.) of 2- (2-bromophenyl) -3- (dibenzo [ b, d ]]Furan-1-yl) benzo [4,5]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 13(14.45g, yield)The rate was 67%). [ M + H ]]+＝744
Synthesis example 14
10.0g (1.0 equivalent) of Compound A, 18.24g (1.1 equivalent) of 3- (5-bromo- [1,1' -biphenyl]-2-yl) -2- (naphthalen-1-yl) benzofuro [2,3-b]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 14(17.81g, yield 74%). [ M + H ]]+＝764
Synthesis example 15
10.0g (1.0 equivalent) of Compound A, 21.16g (1.1 equivalent) of 4- (4-bromonaphthalen-1-yl) -2- (triphenylen-2-yl) benzo [ h ]]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 15(17.90g, yield 67%). [ M + H ]]+＝848
Synthesis example 16
Convert 10.0g (1.0 eq.) intoCompound A, 19.63g (1.1 equiv.) of 2- (4-bromonaphthalen-2-yl) -4- (dibenzo [ b, d ]]Thien-1-yl) benzo [ h]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 16(15.45g, yield 61%). [ M + H ]]+＝804
Synthesis example 17
10.0g (1.0 equivalent) of Compound A, 16.86g (1.1 equivalent) of 2- (2-bromophenyl) -3- (4-phenylnaphthalen-1-yl) quinoxaline, 0.16g (0.01 equivalent) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 17(13.00g, yield 57%). [ M + H ]]+＝724
Synthesis example 18
10.0g (1.0 equivalent) of Compound B, 11.44g (1.1 equivalent) of 2-chloro-3- (naphthalen-2-yl) benzofuro [2,3-B ] are introduced]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Washing with water, andthe pressure was reduced twice to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 18(11.75g, yield 61%). [ M + H ]]+＝612
Synthesis example 19
10.0g (1.0 equivalent) of Compound B, 13.73g (1.1 equivalent) of 3-chloro-2- (dibenzo [ B, d ]) was added]Furan-3-yl) -9, 9-dimethyl-9H-indeno [1,2-b]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 19(12.17g, yield 57%). [ M + H ]]+＝678
Synthesis example 20
10.0g (1.0 eq) of Compound B, 10.61g (1.1 eq) of 3-chloro-9, 9-dimethyl-2-phenyl-9H-indeno [1,2-B ] are introduced]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 20(10.92g, yield 59%). [ M + H ]]+＝588
Synthesis example 21
10.0g (1.0 equivalent) of Compound B, 13.14g (1.1 equivalent) of 3- (9H-carbazol-9-yl) -1-chlorobenzo [ f]Quinazoline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 21(11.24g, yield 54%). [ M + H ]]+＝661
Synthesis example 22
10.0g (1.0 equivalent) of Compound B, 11.79g (1.1 equivalent) of 3-chloro-2- (naphthalen-2-yl) benzo [ f]Quinoxaline, 0.16g (0.01 eq) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 22(11.16g, yield 57%). [ M + H ]]+＝622
Synthesis example 23
10.0g (1.0 equivalent) of Compound B, 8.50g (1.1 equivalent) of 2-chloro-3- (phenyl-d 5) quinoxaline, 0.16g (0.01 equivalent) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 23(11.11g, yield 67%). [ M + H ]]+Synthesis example 24 (527)
10.0g (1.0 equivalent) of Compound B, 8.32g (1.1 equivalent) of 2-chloro-3-phenylquinoxaline, 0.16g (0.01 equivalent) of Pd (t-Bu)3P)213.39g (2.0 equiv.) of K3PO4Added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 24(11.34g, yield 69%). [ M + H ]]+＝522
Synthesis example 25
10.0g (1.0 equivalent) of Compound B, 19.49g (1.1 equivalent) of 2- (4 '-bromo- [1,1' -biphenyl]-4-yl) -3- (4- (naphthalen-2-yl) phenyl) quinoxaline, 0.16g (0.01 eq) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. Subjecting it to column chromatography to obtain a compoundProduct 25(17.64g, yield 70%). [ M + H ]]+＝800
Synthesis example 26
10.0g (1.0 equivalent) of Compound B, 19.28g (1.1 equivalent) of 3- (4-bromonaphthalen-1-yl) -2- (dibenzo [ B, d ]]Furan-3-yl) benzo [4,5]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 26(18.00g, yield 72%). [ M + H ]]+＝794
Synthesis example 27
10.0g (1.0 equivalent) of Compound B, 18.10g (1.1 equivalent) of 3- (3-bromophenyl) -2- (dibenzo [ B, d ]]Thien-3-yl) benzo [4,5]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 27(16.03g, yield 67%). [ M + H ]]+＝760
Synthesis example 28
10.0g (1.0 equivalent) of Compound B, 19.08g (1.1 equivalent) of 3- (4-bromonaphthalen-1-yl) -2- (phenanthren-2-yl) benzofuro [2,3-B]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 28(15.88g, yield 64%). [ M + H ]]+＝788
Synthesis example 29
10.0g (1.0 equivalent) of Compound B, 19.08g (1.1 equivalent) of 3- (3-bromophenyl) -2- (triphenylen-2-yl) benzofuro [2,3-B ] are introduced]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. Column chromatography was performed thereon to obtain compound 29(17.62g, yield 71%). [ M + H ]]+＝788
Synthesis example 30
10.0g (1.0 equiv) of Compound B, 17.06g (1.1 equiv) of 3- ([1,1' -Biphenyl)]-4-yl) -2- (4-bromophenyl) benzo [4,5 ]]Thieno [2,3-b ]]Pyrazine, 0.16g (0.01 eq.) of Pd (t-Bu)3P)26.06g (2.0 equivalents) of NaOtBu are added to 250ml of xylene, refluxed and stirred. After 2 hours the reaction was complete, the solvent was removed under reduced pressureAnd (3) preparing. Then, completely dissolved in CHCl3The mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Ethyl acetate was again added under reflux to allow the crystals to fall, cooled and filtered. This was subjected to column chromatography to give compound 30(17.01g, yield 74%). [ M + H ]]+＝730
< Experimental example >
Comparative example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated to a thin film thickness of (2) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was added
And the following a-1 compound was p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film having a thickness
The hole transport layer of (1). Then, on the hole transport layer, the film thickness
The following EB-1 compound was vacuum-evaporated to form an electron blocking layer. Then, in the above EB-1 vapor deposition film formed by vacuum vapor deposition of RH-1 compound and Dp-7 compound at a weight ratio of 98:2
A thick red light emitting layer. On the light-emitting layer, the thickness of the film
A hole-blocking layer was formed by vacuum vapor deposition of the following HB-1 compound. Next, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1 to form a hole blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Examples 1 to 30
An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compound shown in table 1 below was used instead of RH-1 in the organic light-emitting device of comparative example 1.
Comparative examples 2 to 21
An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compound shown in table 1 below was used instead of RH-1 in the organic light-emitting device of comparative example 1.
[ comparative example Compound ]
When a current was applied to the organic light-emitting devices manufactured in examples 1 to 30 and comparative examples 1 to 21, the voltage, efficiency, 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 (10000 nits) to 95%.
[ Table 1]
The red organic light-emitting device of comparative example 1 used a substance that has been widely used conventionally. Comparative examples 2 to 21 organic light emitting devices were manufactured using C-1 to C-20 instead of RH-1. As seen from the results in table 1, when the compound of the present invention is used as a host of a red light-emitting layer, the driving voltage is greatly reduced by about 20% and the efficiency is improved by 20% or more as compared with the comparative example, and thus it is understood that the energy transfer from the host to the red dopant is favorably performed. Further, it was confirmed that the life characteristics were greatly improved by 1.5 times or more while maintaining high efficiency. It can be judged that this is because the compounds of the present invention have high stability to electrons and holes and a good balance of electron and hole migration in the red device of the OLED compared to the compounds not satisfying the structure of chemical formula 1 of the present invention (comparative examples 10 to 15 and 21) or not satisfying Ar of the present invention (comparative examples 2 to 21). In summary, it was confirmed that when the compound of the present invention is used as a host of a red light emitting layer, driving voltage, light emitting efficiency and life characteristics of an organic light emitting device can be improved.
Claims (9)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second,
x1 is NR and X2 is a direct bond; or X1 is a direct bond and X2 is NR,
a is benzene, and the content of A is,
r is represented by the following chemical formula 2,
chemical formula 2
L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and
ar is any one selected from the following structural formulas,
r' is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
x is an integer of 0 to 5,
y is an integer of 0 to 7,
wherein x or y is 2 or more, the substituents in parentheses are the same as or different from each other, and
a is 1 or 2, and a is,
wherein when a is 2, the substituents in parentheses are the same as or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is a compound represented by the following chemical formula 1-1:
chemical formula 1-1
In the chemical formula 1-1,
r is as defined in claim 1.
3. The compound according to claim 1, wherein the chemical formula 1 is a compound represented by the following chemical formula 1-2:
chemical formula 1-2
In the chemical formula 1-2,
r is as defined in claim 1.
4. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is selected from the group consisting of:
5. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face 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 contain the compound according to any one of claims 1 to 4.
6. The organic light emitting device of claim 5, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises the compound.
7. The organic light emitting device of claim 5, wherein the organic layer comprises a hole injection layer or a hole transport layer,
wherein the hole injection layer or the hole transport layer comprises the compound.
8. An organic light-emitting device according to claim 5 wherein the organic layer comprises an electron-transporting layer or an electron-injecting layer, the electron-transporting layer or the electron-injecting layer comprising the compound.
9. The organic light emitting device according to claim 5, wherein the organic light emitting device further comprises 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, and a hole blocking layer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20180133609 | 2018-11-02 | ||
| KR10-2018-0133609 | 2018-11-02 | ||
| PCT/KR2019/014746 WO2020091522A1 (en) | 2018-11-02 | 2019-11-01 | Compound and organic light emitting device comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112533912A true CN112533912A (en) | 2021-03-19 |
| CN112533912B CN112533912B (en) | 2024-01-02 |
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| KR (1) | KR102312478B1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113512043A (en) * | 2021-08-17 | 2021-10-19 | 浙江华显光电科技有限公司 | Organic compound, preparation, organic light-emitting device, and display or lighting device |
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| JP2022108268A (en) | 2021-01-12 | 2022-07-25 | 保土谷化学工業株式会社 | Organic thin film used for photoelectric conversion element, and photoelectric conversion element thereof |
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| WO2013009095A1 (en) * | 2011-07-11 | 2013-01-17 | 주식회사 두산 | Triphenylene-based compound and organic electroluminescent diode using same |
| KR20150141272A (en) * | 2014-06-09 | 2015-12-18 | 삼성디스플레이 주식회사 | Organic light- emitting devices |
| KR20160055556A (en) * | 2014-11-10 | 2016-05-18 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| WO2017118137A1 (en) * | 2016-01-07 | 2017-07-13 | 广州华睿光电材料有限公司 | Carbazole derivative, and high polymer, mixture, composition and organic electronic device comprising same, and use thereof |
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| KR101771531B1 (en) | 2010-03-25 | 2017-08-28 | 에스에프씨 주식회사 | Spiro compound and organic electroluminescent devices comprising the same |
| KR20120038056A (en) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| KR102122340B1 (en) * | 2016-12-02 | 2020-06-12 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
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- 2019-11-01 WO PCT/KR2019/014746 patent/WO2020091522A1/en active Application Filing
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2013009095A1 (en) * | 2011-07-11 | 2013-01-17 | 주식회사 두산 | Triphenylene-based compound and organic electroluminescent diode using same |
| KR20150141272A (en) * | 2014-06-09 | 2015-12-18 | 삼성디스플레이 주식회사 | Organic light- emitting devices |
| KR20160055556A (en) * | 2014-11-10 | 2016-05-18 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| WO2017118137A1 (en) * | 2016-01-07 | 2017-07-13 | 广州华睿光电材料有限公司 | Carbazole derivative, and high polymer, mixture, composition and organic electronic device comprising same, and use thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113512043A (en) * | 2021-08-17 | 2021-10-19 | 浙江华显光电科技有限公司 | Organic compound, preparation, organic light-emitting device, and display or lighting device |
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| Publication number | Publication date |
|---|---|
| CN112533912B (en) | 2024-01-02 |
| WO2020091522A1 (en) | 2020-05-07 |
| KR20200050897A (en) | 2020-05-12 |
| KR102312478B1 (en) | 2021-10-14 |
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