CN110268036B - Organic light emitting element - Google Patents
Organic light emitting element Download PDFInfo
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- CN110268036B CN110268036B CN201880010433.1A CN201880010433A CN110268036B CN 110268036 B CN110268036 B CN 110268036B CN 201880010433 A CN201880010433 A CN 201880010433A CN 110268036 B CN110268036 B CN 110268036B
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- emitting element
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 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
- 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 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
- 238000012423 maintenance Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([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
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- 125000002255 pentenyl 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
- 150000002987 phenanthrenes Chemical class 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
- 150000003057 platinum Chemical class 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
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- XMYLDITUFLHWLR-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 XMYLDITUFLHWLR-UHFFFAOYSA-N 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 238000011160 research Methods 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
- 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
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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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Abstract
The invention provides an organic light emitting element.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2017-0089708, 2017, 7, 14, inclusive, and the entire contents disclosed in the documents of this korean patent application are incorporated as part of the present specification.
The present invention relates to an organic light emitting element.
Background
Generally, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, an excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, so that a great deal of research is being conducted.
An organic light-emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the 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, 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 element, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to the ground state.
As for organic materials used for such organic light-emitting devices, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 1) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The invention provides an organic light emitting element.
Means for solving the problems
The invention provides an organic light-emitting element, which comprises: the organic light emitting device includes an anode, a cathode facing the anode, and one or more organic layers between the anode and the cathode, wherein the organic layers include a light emitting layer, the light emitting layer includes a compound represented by chemical formula 1, and the anode and the light emitting layer include a compound represented by chemical formula 2 therebetween.
[ chemical formula 1]
In the chemical formula 1 described above,
L 1 is a single bond, or substituted or unsubstituted C 6-60 An arylene group, a cyclic or cyclic alkylene group,
L 2 is a single bond, substituted or unsubstituted C 6-60 Arylene group, or substituted or unsubstituted C containing 1 or more of O, N, si and S 2-60 A heteroarylene group, a heteroaryl group,
Y 1 to Y 3 Each independently is N or C-R 1 And at least any one is N, R 1 Is hydrogen or substituted or unsubstituted C 1-40 An alkyl group, a carboxyl group,
Ar 1 and Ar 2 Each independently is substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing 1 or more of O, N, si and S 2-60 (ii) a heteroaryl group, wherein,
Ar 3 is substituted or unsubstituted C 6-60 An aryl group which is a radical of an aromatic group,
m is an integer of 1 to 2,
[ chemical formula 2]
In the chemical formula 2 as described above,
Ar 4 and Ar 5 Each independently substituted or unsubstituted C 6-60 An aryl group which is a radical of an aromatic group,
R 1 and R 2 Each independently is substituted or unsubstituted C 6-20 An aryl group, a heteroaryl group,
n1 and n2 are each independently 0 or 1.
Effects of the invention
The present invention uses the compound represented by the above chemical formula 1 as a host material of a light emitting layer and uses the compound represented by the above chemical formula 2 as a material of an organic layer between an anode and the light emitting layer, thereby being capable of providing an organic light emitting element which can realize low voltage driving and exhibit high efficiency and long life characteristics.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 5, an electron blocking layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides an organic light emitting element in which a light emitting layer contains a compound represented by the above chemical formula 1, and a compound represented by the above chemical formula 2 is contained between an anode and the light emitting layer.
In the context of the present specification,
represents a bond with another compound, and a single bond means a bond represented by L 1 Or L 2 The portion represented does not have other atoms. For example, when L of chemical formula 1 1 Is a single bond, Y 1 To Y 3 When is N, by Ar 1 And Ar 2 The substituted triazine substituent may be attached directly to the dibenzofuran.
In the present specification, the term "substituted or unsubstituted" may mean substituted with R a Substituted or unsubstituted, R a May be deuterium; a halogen group; a cyano group; a nitro group; an amino group; an alkyl group having 1 to 40 carbon atoms; a haloalkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted heteroalkyl group containing one or more carbon atoms of 1 to 40 of O, N, si and S; a substituted or unsubstituted heterohaloalkyl group having 1 to 40 carbon atoms containing one or more of O, N, si and S; or an alkenyl group having 2 to 40 carbon atoms.
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group having 1 to 40 carbon atoms may be a linear, branched or cyclic alkyl group. Specifically, the alkyl group having 1 to 40 carbon atoms may be a straight-chain alkyl group having 1 to 40 carbon atoms, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 40 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms. More specifically, the alkyl group having 1 to 40 carbon atoms may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a cyclohexyl group or the like. But is not limited thereto.
In the heteroalkyl group having 1 to 40 carbon atoms in the present specification, one or more carbon atoms of the alkyl group may be independently substituted with O, N, si or S. For example, as an example of the straight-chain alkyl group, the heteroalkyl group substituted with O for the carbon number 1 of the N-butyl group is an N-propoxy group, the heteroalkyl group substituted with N is an N-propylamino group, the heteroalkyl group substituted with Si is an N-propylsilyl group, and the heteroalkyl group substituted with S is an N-propylthio group. Further, as examples of the branched alkyl group, a heteroalkyl group substituted with O for carbon number 1 of the neopentyl group is a tert-butoxy group, a heteroalkyl group substituted with N is a tert-butylamino group, a heteroalkyl group substituted with Si is a tert-butylsilyl group, and a heteroalkyl group substituted with S is a tert-butylthio group. Further, as examples of the cyclic alkyl group, a heteroalkyl group substituted with O at carbon No. 2 of the cyclohexyl group is 2-tetrahydropyranyl (2-tetrahydropyranyl), a heteroalkyl group substituted with N is 2-piperidinyl, a heteroalkyl group substituted with Si is 1-sila-cyclohexyl (1-sila-cyclohexenyl), and a heteroalkyl group substituted with S is 2-tetrahydrothiopyranyl (2-tetrahydrothiopyranyl). Specifically, the heteroalkyl group of carbon number 1 to 40 may be a linear, branched, or cyclic hydroxyalkyl group of carbon number 1 to 40; a linear, branched, or cyclic alkoxy group having 1 to 40 carbon atoms; a linear, branched, or cyclic alkoxyalkyl group having 2 to 40 carbon atoms; a linear, branched, or cyclic aminoalkyl group having 1 to 40 carbon atoms; a linear, branched, or cyclic alkylamino group having 1 to 40 carbon atoms; a linear, branched, or cyclic alkylaminoalkyl group having 1 to 40 carbon atoms; a linear, branched, or cyclic silylalkyl (oxy) group having 1 to 40 carbon atoms; a linear, branched, or cyclic alk (oxy) silyl group having 1 to 40 carbon atoms; a linear, branched, or cyclic alk (oxy) ylsilylalkyl (oxy) group of 1 to 40 carbon atoms; a linear, branched, or cyclic mercaptoalkyl group having 1 to 40 carbon atoms; a straight, branched, or cyclic alkylthio group having 1 to 40 carbon atoms; or a linear, branched, or cyclic alkylthioalkyl group having 2 to 40 carbon atoms. More specifically, examples of the heteroalkyl group having 1 to 40 carbon atoms include a hydroxymethyl group, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a tert-butoxy group, a cyclohexyloxy group, a methoxymethyl group, an isopropoxymethyl group, a cyclohexyloxymethyl group, a 2-tetrahydropyranyl group (2-tetrahydropyranyl group), an aminomethyl group, a methylamino group, a n-propylamino group, a tert-butylamino group, a methylaminopropyl group, a 2-piperidyl group, a n-propylsilyl group, a trimethylsilyl group, a dimethylmethoxysilyl group, a tert-butylsilyl group, a 1-sila-cyclohexyl group (1-sila-cyclohexylgroup), a n-propylthio group, a tert-butylthio group, and a 2-tetrahydrothiopyranyl group (2-tetrahydrothiopyranyl group). But is not limited thereto.
In the present specification, the alkenyl group having 2 to 40 carbon atoms may be a linear, branched, or cyclic alkenyl group. Specifically, the alkenyl group having 2 to 40 carbon atoms may be a linear alkenyl group having 2 to 40 carbon atoms; a linear alkenyl group having 2 to 20 carbon atoms; a linear alkenyl group having 2 to 10 carbon atoms; a branched alkenyl group having 3 to 40 carbon atoms; a branched alkenyl group having 3 to 20 carbon atoms; a branched alkenyl group having 3 to 10 carbon atoms; a cyclic alkenyl group having 5 to 40 carbon atoms; a cyclic alkenyl group having 5 to 20 carbon atoms; or a cyclic alkenyl group having 5 to 10 carbon atoms. More specifically, the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a cyclohexenyl group, or the like. But is not limited thereto.
In the present specification, the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group. Specifically, the aryl group of carbon number 6 to 60 may be a monocyclic or polycyclic aryl group of carbon number 6 to 30; or a monocyclic or polycyclic aromatic group of 6 to 20 carbon atoms. More specifically, the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group such as phenyl, biphenyl, or terphenyl group, and the polycyclic aryl group may be naphthyl, anthryl, tetracenyl, phenanthryl, triphenylenyl, fluoranthryl, pyrenyl, perylenyl, perylene, or the like,
A phenyl group, or a fluorenyl group.
In addition, the aryl group having 6 to 60 carbon atoms may have a structure in which two or more selected from a monocyclic aryl group and a polycyclic aryl group are connected to each other. Specifically, the aryl group having 6 to 60 carbon atoms may have a structure in which a polycyclic aryl group and/or a monocyclic aryl group is connected to a polycyclic aryl group. More specifically, the present invention is to provide a novel, the aryl group having 6 to 60 carbon atoms may be a naphthyl phenyl group, an anthryl phenyl group, a phenanthryl phenyl group, a triphenylenyl phenyl group, a pyrenyl phenyl group, a perylenyl phenyl group, a,
Phenyl, fluorenyl phenyl, phenyl naphthyl, phenyl anthracenyl, phenyl terphenyl, or phenyl naphthylphenyl, and the like. But is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, it may be
And so on. But is not limited thereto.
In the heteroaryl group having 2 to 60 carbon atoms in the present specification, 1 or more carbon atoms of the aryl group may be independently substituted by O, N, si or S. For example, a heteroaryl group in which carbon number 9 of the fluorenyl group is substituted with O is a dibenzofuranyl group, a heteroaryl group substituted with N is a carbazolyl group, a heteroaryl group substituted with Si is a 9-sila-fluorenyl group, and a heteroaryl group substituted with S is a dibenzothiophenyl group. Specifically, the heteroaryl group having 2 to 60 carbon atoms may be a heteroaryl group having 2 to 30 carbon atoms; or a heteroaryl group having 2 to 20 carbon atoms. More specifically, the heteroaryl group having 2 to 60 carbon atoms may be a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group,
Azolyl group,
<xnotran> , , , , , , , , , , , , , , , , , , , , </xnotran>
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Azole group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but not limited thereto.
In the present specification, arylene means a 2-valent organic group from which any one of hydrogen radicals of the above-mentioned aryl group is removed, and heteroarylene means a 2-valent organic group from which any one of hydrogen radicals of the above-mentioned heteroaryl group is removed.
In the above chemical formula 1, L 1 May be a single bond or phenylene group, and more specifically, may be a single bond.
In the above chemical formula 1, Y 1 To Y 3 May each independently be N or C-H, and at least any one is N.
In the above chemical formula 1, ar 1 And Ar 2 Can be respectively and independently selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, 9-dimethyl fluorene, 9-diphenyl fluorene and spiro [ fluorene-9, 9' -fluorene]1-valent residues of aromatic or heteroaromatic hydrocarbons in dibenzofuran, dibenzothiophene, N-phenylcarbazole, phenyl-9, 9-dimethylfluorene, phenyldibenzofuran and phenyldibenzothiophene.
Specifically, ar 1 And Ar 2 May each independently be a 1-valent residue derived from an aromatic hydrocarbon selected from benzene, biphenyl, and terphenyl.
More specifically, ar 1 And Ar 2 May each independently be phenyl or biphenyl.
In the above chemical formula 1, L 2 Can be a single bond or can be derived from benzene, naphthalene, 9-dimethylfluorene, 9-diphenylfluorene, spiro [ fluorene-9, 9' -fluorene]Dibenzofuran, dibenzothiophene, benzothieno [2,3-d ]]Pyrimidine (benzothieno [2, 3-d)]pyrimidene) and benzothieno [3,2-d]Pyrimidine (benzothieno [3, 2-d)]pyrimidene) of an aromatic or heteroaromatic group.
In the above chemical formula 1, ar 3 Can be derived from benzene, biphenyl, terphenyl, naphthalene, anthracene, tetracene,
(chrysene), phenanthrene, triphenylene, fluoranthene (Fluoranthene), pyrene (pyrene) and perylene (perylene) are the 1-valent residues of aromatic hydrocarbons.
In the above chemical formula 1, L 2 -Ar 3 May be a substituent selected from the following substituents.
The compound represented by the above chemical formula 1 may be a compound selected from the group consisting of compounds represented by the following chemical formulae 1-1 and 1-2.
[ chemical formula 1-1]
In the above-mentioned chemical formula 1-1,
L 1 、Y 1 to Y 3 、Ar 1 And Ar 2 In the same manner as in the chemical formula 1,
L 2a is a single bond, substituted or unsubstituted C 6-60 Arylene group, or substituted or unsubstituted C containing 1 or more of O, N, si and S 2-60 A heteroarylene group, a heteroaryl group,
Ar 3a is substituted or unsubstituted C 6-60 An aryl group, a heteroaryl group,
[ chemical formulas 1-2]
In the above-mentioned chemical formula 1-2,
L 1 、Y 1 to Y 3 、Ar 1 And Ar 2 In the same manner as in the chemical formula 1,
L 2b and L 2c Each independently a single bond, substituted or unsubstituted C 6-60 Arylene, or substituted or unsubstituted comprising 1 of O, N, si and SC of (A) to 2-60 A heteroarylene group, a heteroaryl group,
Ar 3b and Ar 3c Each independently is substituted or unsubstituted C 6-60 An aryl group which is a radical of an aromatic group,
l of the above chemical formulae 1-1 and 1-2 1 、Y 1 To Y 3 、Ar 1 And Ar 2 And L of chemical formula 1 1 、Y 1 To Y 3 、Ar 1 And Ar 2 Same, L 2a To L 2c And L of chemical formula 1 2 Corresponding to Ar 3a To Ar 3c With chemical formulae 1 and Ar 3 Corresponding to, L 1 And L 2 、Y 1 To Y 3 、Ar 1 To Ar 3 Since specific examples of (2) have been described in detail above, detailed descriptions thereof are omitted here.
The compound represented by the above chemical formula 1 may be selected from the following compounds.
In the above chemical formula 2, ar 4 And Ar 5 Can be independently selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, phenyl terphenyl and benzeneNaphthalene, phenylphenanthrene, 9-dimethylfluorene, 9-diphenylfluorene and spiro [ fluorene-9, 9' -fluorene]The 1-valent residue of aromatic hydrocarbon in (1).
Specifically, ar 4 And Ar 5 May each independently be a 1-valent residue derived from an aromatic hydrocarbon selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, phenyl terphenyl, phenyl naphthalene, and phenyl phenanthrene.
In the above chemical formula 2, R 1 And R 2 Is phenyl, n1 and n2 may each independently be 0 or 1. N1 or n2 is 0 means that the carbazolyl group of the formula 2 is not substituted by R 1 Or R 2 And (4) substitution.
The compound represented by the above chemical formula 2 may be selected from the following compounds.
The organic light-emitting element of the present invention includes an anode, a cathode provided to face the anode, and one or more organic material layers provided between the anode and the cathode. The organic layer is formed of a multilayer structure in which two or more organic layers are stacked. Specifically, the organic layer may include a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, an electron blocking layer provided on the hole transport layer, and a light emitting layer provided on the electron blocking layer. The organic light-emitting element may include an electron transport layer, an electron injection layer, and the like between the light-emitting layer and the cathode. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.
The organic light emitting element according to the present invention may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting element according to the present invention may be an inverted (inverted) type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting element according to an embodiment of the present invention is illustrated in fig. 1.
Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 5, an electron blocking layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 is contained in the light emitting layer 7, and the compound represented by the above chemical formula 2 is contained in one or more organic layers among the hole injection layer 3, the hole transport layer 5, and the electron injection layer 6, so that the driving voltage of the organic light emitting element can be reduced, and the efficiency and the lifetime can be improved.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that the compound represented by chemical formula 1 is contained in the light emitting layer, and the compound represented by chemical formula 2 is contained in one or more organic layers among the hole injection layer, the hole transport layer, and the electron blocking layer. In addition, the plurality of organic layers may be formed of the same substance or different substances.
For example, the organic light emitting element according to the present invention can be manufactured by sequentially laminating any one of an anode and a cathode, an organic layer, and the other one of the anode and the cathode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method, forming an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting element may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In addition, with respect to the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2, in manufacturing an organic light emitting element, an organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. 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.
The anode material is preferably a material having a large work function in order to smoothly inject holes 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 Al or SNO 2 A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And a multi-layer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to 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 is excellent in thin-film formability. As the hole injecting substance, a compound represented by the above chemical formula 2 or a conventional compound known as a hole injecting substance can be used. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode 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.
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 as a material forming the hole transport layer, a compound represented by the above chemical formula 2 can be used. The compound represented by the above chemical formula 2 has already been described in detail in the foregoing, and thus a detailed description is omitted here.
Since the compound represented by the above chemical formula 2 has a large hole mobility, it is suitable for receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer.
On the other hand, if the hole injection layer or the electron blocking layer is formed of the compound represented by the above chemical formula 2, the above hole transport layer may be formed of a hole transport material well known in the art to which the present invention pertains. Specific examples of such a hole-transporting substance include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
An electron blocking layer may be formed between the hole transport layer and the light emitting layer so that electrons transferred to the light emitting layer cannot move toward the anode side. As such a material forming the electron blocking layer, a compound represented by the above chemical formula 2 may be used. In particular, when the electron blocking layer is formed using the compound represented by the above chemical formula 2, the efficiency of the organic light emitting element can be significantly improved.
The light-emitting layer is a layer 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 may include a host material and a dopant material.
As the host material, the compound represented by the above chemical formula 1 may be used. The compound represented by the above chemical formula 1 has already been described in detail in the foregoing, and thus a detailed description is omitted here.
In addition, as the host material, a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula 3 may be used.
[ chemical formula 3]
In the chemical formula 3 above, the first and second,
Ar 7 and Ar 8 Each independently is substituted or unsubstituted C 6-60 And (4) an aryl group.
In the above chemical formula 3, ar 7 And Ar 8 Can be respectively and independently selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, 9-dimethyl fluorene, 9-diphenyl fluorene and spiro [ fluorene-9, 9' -fluorene]And 1-valent residues of aromatic hydrocarbons in phenyl terphenyl, phenyl naphthalene and phenyl phenanthrene.
The compound represented by the above chemical formula 3 may be selected from the following compounds.
The light emitting layer may include a host material known in the art to which the present invention pertains, in addition to the compounds represented by the above chemical formulas 1 and 3. Specific examples of such host materials include aromatic fused ring derivatives and heterocyclic compounds. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,
Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
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 inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. Specific examples thereof include an Al complex of 8-hydroxyquinoline and an Al complex containing Alq 3 The 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 is a layer for injecting electrons from the electrode, and is preferably a compound of: has the ability to transport electrons, has an electron injection effect from the cathode, and is excellent in electron injection into the light-emitting layer or the light-emitting materialThis prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer, and is excellent in thin-film formability. Specifically, fluorenone, anthraquinone dimethane (Anthraquinodimethane), 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, but are not limited to, lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolato) chloride, gallium bis (2-methyl-8-quinolinolato) (o) gallium, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, and gallium bis (2-methyl-8-quinolinolato) (2-naphthol) gallium.
The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
The fabrication of the organic light emitting element described above is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
EXAMPLE 1 production of organic light-emitting element
Will be provided with
The glass substrate coated with ITO (indium tin oxide) in the thickness of (a) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent was prepared by Fisher Co, and the distilled water was filtered by a filter (Millipore Co.) manufactured by Millipore CoSecondary distilled water. After washing the ITO substrate for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing, the ITO substrate was ultrasonically washed with isopropyl alcohol, acetone, and methanol solvents, dried, and then transported to a plasma cleaning machine. The ITO substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.
On the ITO electrode thus prepared, to
The following compound HI-1 was thermally vacuum-evaporated to form a hole injection layer. On the hole injection layer, the following compound HT-1 and
is formed by thermal vacuum deposition, and the following compound 2-1 is deposited on the hole transport layer
The electron blocking layer is formed by vacuum evaporation. Then, the following compound 1-1 and 6 wt% of phosphorescent dopant YGD-1 based on the weight of the compound 1-1 were co-evaporated on the electron blocking layer to obtain a phosphor layer
The thickness of (2) forms a light emitting layer. On the light-emitting layer, the following compound ET-1 and
is vacuum-evaporated to form an electron transporting layer, and the following compound ET-2 and 2 wt% of Li relative to the weight of the compound ET-2 are co-evaporated to form a layer
The thickness of (2) forms an electron injection layer. On the electron injection layer to
Aluminum is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Aluminum maintenance
The vacuum degree is maintained at 1X 10 during the vapor deposition -7 ～5×10 -8 And (4) supporting to manufacture the organic light-emitting element.
Examples 2 to 16 production of organic light-emitting element
An organic light-emitting element was produced in the same manner as in example 1, except that the compound for forming the electron blocking layer and/or the light-emitting layer was changed as shown in table 1 below. In the following Table 1, the compounds 1-2, 1-3, 1-4, 2-2, 2-3 and 2-4 are as follows, respectively.
Comparative examples 1 to 15 production of organic light-emitting elements
An organic light-emitting element was produced in the same manner as in example 1, except that the compound for forming the electron blocking layer and/or the light-emitting layer was changed as shown in table 1 below. In Table 1 below, HT-2, HT-3, YGH-1 and YGH-2 compounds are as follows, respectively.
Experimental example evaluation of organic light-emitting element
At 10mA/cm 2 At a current density of (2), measuring the rootThe results of the voltage, efficiency and lifetime of the organic light emitting elements manufactured according to examples 1 to 16 and comparative examples 1 to 15 described above are shown in table 1. The above-mentioned lifetime (LT 95) means the time required for reduction to 95% of the initial luminance (6000 nit) and is at 20mA/cm 2 Is measured at the current density of (2).
[ Table 1]
Organic light-emitting elements using existing compounds are shown in table 1 above (comparative examples 1 to 3); organic light emitting devices using the compound represented by the above chemical formula 2 as an electron blocking layer, but using the existing compound as a material for a light emitting layer (comparative examples 4 to 7); and basic characteristics of organic light emitting elements (comparative examples 8 to 11) using the compound represented by the above chemical formula 1 as a light emitting layer material, but using an existing compound as an electron blocking layer material.
It can be confirmed from comparative examples and comparative examples that the compounds represented by the above chemical formulas 1 and 2 are used as materials of the light emitting layer and the electron blocking layer, respectively, and exhibit a low driving voltage, high efficiency, and a long life compared to the conventional organic light emitting element. In particular, when the compound 2-2 is used as an electron blocking layer material, the driving voltage is the lowest and the efficiency is the highest, and when the compound 1-3 is used as a light emitting layer material, the lifetime is the longest.
On the other hand, in comparative examples 1 to 15, in comparative examples 4 to 7 in which the electron blocking layer material was changed to the compound represented by the above chemical formula 2, and comparative examples 12 to 15, the efficiency was improved, and in comparative examples 8 to 11 in which the light emitting layer material was changed to the compound represented by the above chemical formula 1, the lifetime was improved. But do not exhibit the efficiency and lifetime of the embodiment level.
From this, it was confirmed that the organic light emitting device of the present invention includes a compound having a structure in which an arylamine having a biphenylamine type bond is substituted at the position 9 of the carbazolyl group as shown in the above chemical formula 2 between the anode and the light emitting layer to exhibit improved efficiency, and includes a compound having a structure in which a triazinyl group having very excellent electron injection ability and thermal stability is substituted at the position 4 of the dibenzofuranyl group having electron stability as shown in the above chemical formula 1 in the light emitting layer to exhibit low driving voltage and improved efficiency, and also exhibit long life.
Description of the symbols
1: substrate 2: anode
3: hole injection layer 4: cathode electrode
5: hole transport layer 6: electron blocking layer
7: light-emitting layer 8: an electron transport layer.
Claims (9)
1. An organic light-emitting element comprising: an anode, a cathode provided so as to face the anode, and one or more organic material layers provided between the anode and the cathode,
the organic layer includes a light-emitting layer,
the light emitting layer includes a compound represented by the following chemical formula 1,
a compound represented by the following chemical formula 2 is included between the anode and the light emitting layer:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
L 1 is a single bond or a phenylene group,
L 2 is a single bond or is derived from a group selected from benzene, naphthalene, benzothieno [2,3-d]Pyrimidine and benzothieno [3,2-d ]]The 2-valent residue of an arene or heteroarene in a pyrimidine,
Y 1 to Y 3 Each of which is independently a member of the group N,
Ar 1 and Ar 2 Each independently is C 6-30 Aryl group, or C containing 1 or more of O, N, si and S 2-30 (ii) a heteroaryl group, wherein,
Ar 3 is C 6-30 An aryl group which is a radical of an aromatic group,
m is an integer of 1 to 2,
chemical formula 2
In the chemical formula 2, the first and second organic solvents,
Ar 4 and Ar 5 Each independently is C 6-30 An aryl group, a heteroaryl group,
R 1 and R 2 Each independently is C 6-20 An aryl group, a heteroaryl group,
n1 and n2 are each independently 0 or 1.
2. The organic light-emitting element according to claim 1, wherein Ar 1 And Ar 2 Each independently is derived from benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, 9-dimethylfluorene, 9-diphenylfluorene, spiro [ fluorene-9, 9' -fluorene]1-valent residues of aromatic or heteroaromatic hydrocarbons in dibenzofuran, dibenzothiophene, N-phenylcarbazole, phenyl-9, 9-dimethylfluorene, phenyldibenzofuran and phenyldibenzothiophene.
3. The organic light-emitting element according to claim 1, wherein Ar 3 Is derived from benzene, biphenyl, terphenyl, naphthalene, anthracene, tetracene,
1-valent residues of aromatic hydrocarbons in phenanthrene, triphenylene, fluoranthene, pyrene and perylene.
4. The organic light-emitting element according to claim 1, wherein L 2 -Ar 3 Is a substituent selected from the following substituents:
5. the organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 1 is selected from compounds represented by the following chemical formulae 1-1 and 1-2:
chemical formula 1-1
In the chemical formula 1-1,
L 1 、Y 1 to Y 3 、Ar 1 And Ar 2 In the same manner as in the chemical formula 1,
L 2a is a single bond or is derived from a group selected from benzene, naphthalene, benzothieno [2,3-d]Pyrimidine and benzothieno [3,2-d]The 2-valent residue of an arene or heteroarene in a pyrimidine,
Ar 3a is C 6-30 An aryl group which is a radical of an aromatic group,
chemical formula 1-2
In the chemical formula 1-2,
L 1 、Y 1 to Y 3 、Ar 1 And Ar 2 In the same manner as in the chemical formula 1,
L 2b and L 2c Each independently a single bond, or from benzene, naphthalene, benzothieno [2,3-d ]]Pyrimidine and benzothieno [3,2-d]The 2-valent residue of an arene or heteroarene in a pyrimidine,
Ar 3b and Ar 3c Each independently is C 6-30 And (4) an aryl group.
6. The organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 1 is selected from the following compounds:
7. the organic light-emitting element according to claim 1, wherein Ar 4 And Ar 5 Each independently is a compound derived from a group selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, phenyl terphenyl, phenyl naphthalene, phenyl phenanthrene, 9-dimethylfluorene, 9-diphenylfluorene and spiro [ fluorene-9, 9' -fluorene]The 1-valent residue of aromatic hydrocarbon in (1).
8. The organic light-emitting element according to claim 1,
R 1 and R 2 Is a phenyl group, and the phenyl group,
n1 and n2 are each independently 0 or 1.
9. The organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 2 is selected from the following compounds:
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| KR20200093442A (en) | 2019-01-28 | 2020-08-05 | 주식회사 엘지화학 | Organic light emitting device |
| CN110429187B (en) * | 2019-07-05 | 2020-12-08 | 武汉华星光电半导体显示技术有限公司 | Thin film electroluminescent device, preparation method thereof and electronic equipment |
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| CN113678274B9 (en) * | 2019-11-11 | 2023-10-24 | 株式会社Lg化学 | Organic light emitting device |
| WO2021182893A1 (en) * | 2020-03-11 | 2021-09-16 | 주식회사 엘지화학 | Organic light emitting device |
| KR102360903B1 (en) * | 2020-03-11 | 2022-02-09 | 주식회사 엘지화학 | Organic light emitting device |
| WO2021230715A1 (en) * | 2020-05-14 | 2021-11-18 | 주식회사 엘지화학 | Organic light-emitting element |
| EP4238969A1 (en) * | 2020-10-30 | 2023-09-06 | LT Materials Co., Ltd. | Heterocyclic compound, organic light-emitting device comprising same, composition for organic layer of organic light-emitting device, and method for manufacturing organic light-emitting device |
| CN114075176B (en) * | 2020-11-10 | 2023-09-12 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device and electronic device |
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