CN113195456A - Heterocyclic compound and organic light emitting device including the same - Google Patents
Heterocyclic compound and organic light emitting device including the same Download PDFInfo
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- CN113195456A CN113195456A CN202080006996.0A CN202080006996A CN113195456A CN 113195456 A CN113195456 A CN 113195456A CN 202080006996 A CN202080006996 A CN 202080006996A CN 113195456 A CN113195456 A CN 113195456A
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- 238000002347 injection Methods 0.000 claims description 42
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- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000006267 biphenyl group Chemical group 0.000 claims description 31
- 239000012044 organic layer Substances 0.000 claims description 31
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
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- 229910052805 deuterium Inorganic materials 0.000 claims description 27
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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- 150000001339 alkali metal compounds Chemical class 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 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
- 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
- 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
- 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
- 125000005956 isoquinolyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([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
- 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-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
- 239000003960 organic solvent Substances 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
- 229910052763 palladium Inorganic materials 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 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
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PWSROGYYCPXIGK-UHFFFAOYSA-N spiro[benzo[c]fluorene-7,9'-fluorene] Chemical compound C1=CC=CC=2C3=CC=CC=C3C3(C=4C=CC=CC4C=4C5=C(C=CC34)C=CC=C5)C12 PWSROGYYCPXIGK-UHFFFAOYSA-N 0.000 description 1
- AFYJRAFRYWVOOZ-UHFFFAOYSA-N spiro[cyclopentane-1,9'-fluorene] Chemical compound C1CCCC21C1=CC=CC=C1C1=CC=CC=C12 AFYJRAFRYWVOOZ-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 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
- 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
- 125000001544 thienyl 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- Chemical & Material Sciences (AREA)
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Abstract
The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification relates to a heterocyclic compound and an organic light-emitting device including the same.
The present application claims priority to korean patent application No. 10-2019-0052173, filed by 03.05.9.2019, the entire contents of which are incorporated in the present specification.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer 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 two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a 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 a ground state.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
[ Prior Art document ] (patent document 1) laid-open patent publication No. 10-2013-
Disclosure of Invention
Technical subject
The present specification provides heterocyclic compounds and organic light emitting devices comprising the same.
Means for solving the problems
The present specification provides heterocyclic compounds represented by the following chemical formula 1 or 2.
[ chemical formula 1]
[ chemical formula 2]
In the above chemical formula 1 or 2,
l1 is a direct bond, a substituted or unsubstituted 2-to 4-valent phenyl group, a substituted or unsubstituted 2-to 4-valent biphenyl group, or a substituted or unsubstituted 2-to 4-valent terphenyl group,
l2 is a 2-to 4-valent phenyl group, a 2-to 4-valent biphenyl group, or a 2-to 4-valent terphenyl group,
l3 and L4, which are identical to or different from one another, are each independently a direct bond or a substituted or unsubstituted aromatic radical having a valency 2 to 4,
ar1 is a 2-valent group represented by the following chemical formula A1,
m is 0 or 1, and m is,
r1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r2 and r4, which are the same as or different from each other, are each independently an integer of 0 to 4,
a1, a2, b1 and b2, which are the same or different from each other, are each independently an integer of 1 to 3,
when R2 is 2 or more, R2 may be the same or different from each other,
when R4 is 2 or more, R4 may be the same or different from each other,
[ chemical formula A1]
In the above-described chemical formula a1,
x1 and X2 are each hydrogen, or are bonded directly to one another or via-O-or-S-,
any one of Q1 to Q16 is linked to L3 of the above chemical formula 2, and the other is linked to L4 of the above chemical formula 2, and the others are the same or different from each other, and each independently is hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In addition, the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided 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 include a heterocyclic compound represented by the chemical formula 1 or 2.
Effects of the invention
The compound according to one embodiment of the present specification is used in an organic light emitting device, so that a driving voltage of the organic light emitting device can be reduced and light efficiency can be improved. In addition, the thermal stability of the compound is utilized, so that the life characteristics of the device can be improved.
Drawings
Fig. 1 and 2 illustrate an example of an organic light emitting device according to an embodiment of the present specification.
[ description of symbols ]
101: substrate
102: anode
103: hole injection layer
104: a first hole transport layer
105: second hole transport layer
106: luminescent layer
107: electron injection and transport layer
108: cathode electrode
Detailed Description
The present specification will be described in more detail below.
The compound represented by the above chemical formula 1 has one or more cyano groups connected to the end of a core structure in which a quinazoline is connected to a phenylene group or a naphthylene group. The compound represented by the above chemical formula 2 has one or more cyano groups connected to the end of the spiro polycyclic or diphenylfluorene core structure to which the quinazoline is connected. When the compound of the above chemical formula 1 or 2 is used as an electron transport layer or an electron injection layer substance, the long-life characteristics of the organic light emitting device are improved due to an increase in the dipole moment in the molecule.
In addition, the compound represented by chemical formula 1 or 2 has a cyano group connected to the end of the structure, and thus has improved high efficiency and low voltage characteristics as compared to a compound having a cyano group at a different substitution position.
In addition, the compound represented by the above chemical formula 1 does not include a naphthalene linking group at L1 and L2, and high efficiency and low voltage characteristics are improved as compared with the compound including a naphthalene linking group.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
In the context of the present specification,
indicating the location of the connection.
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 deuterium, a halogen group, a cyano group, an alkyl group, an aryl group, and a heteroaryl group containing 1 or more heteroatoms other than carbon atoms, or substituted with substituents formed by connecting 2 or more substituents among the above-exemplified substituents, or having no substituent.
In the context of the present specification,the linkage of 2 or more substituents means that the hydrogen of any one substituent is linked to another substituent. For example, isopropyl and phenyl are linked to form
A substituent of (1).
In the present specification, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, 2 phenyl groups and isopropyl groups are linked to form
A substituent of (1). The same explanation as above applies to the case where 4 or more substituents are bonded.
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 30, 1 to 20, 1 to 10, or 1 to 5. 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-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
In the present specification, aryl means a 1-valent group of a 1-valent aromatic hydrocarbon or aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon refers to a compound containing a planar ring in which pi electrons are completely conjugated, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is fused to an aromatic hydrocarbon. In the present specification, the aryl group includes 2 or more aryl groupsA group having a valence of 1 wherein aromatic hydrocarbons or aromatic hydrocarbon derivatives are bonded to each other. The aryl group is not particularly limited, but is preferably an aryl group having 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the above aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a perylene, a metal, and a metal,
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 present specification, when it is indicated that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which substituents of five-membered rings of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes, but is not limited to, 9 '-spirobifluorene, spiro [ cyclopentane-1, 9' -fluorene ], spiro [ benzo [ c ] fluorene-7, 9-fluorene ] and the like.
In the present specification, the heterocyclic group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, S and the like. The number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Azolyl group,
Examples of the organic solvent include, but are not limited to, diazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, dihydrophenothiazinyl, dihydrobenzisoquinolinyl, and benzopyranyl.
In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the above-mentioned examples of heterocyclic groups.
In the present specification, heteroaryl means an aromatic heterocycle having a valence of 1. Here, the aromatic heterocyclic ring is an aromatic ring or a 1-valent group of an aromatic ring derivative, and represents a group containing at least 1 of O, N and S as a hetero atom in the ring. The aromatic ring derivative includes all of the structures in which an aromatic ring or an aliphatic ring is fused to an aromatic ring. In the present specification, the heteroaryl group includes a 1-valent group in which 2 or more heteroatom-containing aromatic rings or derivatives of the heteroatom-containing aromatic rings are linked to each other. The number of carbon atoms of the above heteroaryl group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13.
The heterocyclic compound represented by the above chemical formula 1 or 2 will be described in detail below.
In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted 2-to 4-valent phenyl group, a substituted or unsubstituted 2-to 4-valent biphenyl group, or a substituted or unsubstituted 2-to 4-valent terphenyl group.
In one embodiment of the present specification, L1 is a direct bond, a2 to 4 valent phenyl group substituted or unsubstituted with a cyano group or an alkyl group, a2 to 4 valent biphenyl group substituted or unsubstituted with a cyano group or an alkyl group, or a2 to 4 valent terphenyl group substituted or unsubstituted with a cyano group or an alkyl group.
In one embodiment of the present specification, L1 is a direct bond, a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group.
In one embodiment of the present specification, L1 is a direct bond, a 2-to 3-valent phenyl group, or a 2-to 3-valent biphenyl group.
In one embodiment of the present specification, L1 is a direct bond, a 2-valent phenyl group, a 2-valent biphenyl group, or a 2-valent terphenyl group.
In another embodiment, L1 is a phenyl group having a valence of 3.
In one embodiment of the present specification, L2 is an unsubstituted 2-to 4-valent phenyl group, an unsubstituted 2-to 4-valent biphenyl group, or an unsubstituted 2-to 4-valent terphenyl group.
In one embodiment of the present specification, L2 is a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group.
In one embodiment of the present specification, L2 is a 2-to 3-valent phenyl group, or a 2-to 3-valent biphenyl group.
In one embodiment of the present specification, L2 is a 2-valent phenyl group, a 2-valent biphenyl group, or a 2-valent terphenyl group.
In another embodiment, L2 is a 3 valent phenyl group, a 3 valent biphenyl group, or a 3 valent terphenyl group.
In one embodiment of the present specification, L3 and L4, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted 2-to 4-valent aryl group.
In one embodiment of the present specification, L3 and L4, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and having 2 to 4 valences.
In one embodiment of the present specification, L3 and L4, which are the same or different from each other, are each independently a direct bond or an aryl group having 6 to 20 carbon atoms and having 2 to 3 valences.
In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted 2-to 4-valent phenyl group, a substituted or unsubstituted 2-to 4-valent biphenyl group, a substituted or unsubstituted 2-to 4-valent terphenyl group, a substituted or unsubstituted 2-to 4-valent naphthyl group, a substituted or unsubstituted 2-to 4-valent fluorenyl group, a substituted or unsubstituted 2-to 4-valent phenanthryl group, a substituted or unsubstituted 2-to 4-valent anthryl group, a substituted or unsubstituted 2-to 4-valent pyrenyl group, or a substituted or unsubstituted 2-to 4-valent pyrenyl group
And (4) a base.
In one embodiment of the present specification, L3 is a direct bond, a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group.
In one embodiment of the present specification, L3 is a direct bond, a 2-to 3-valent phenyl group, or a 2-to 3-valent biphenyl group.
In one embodiment of the present specification, L3 is a direct bond, a 2-valent phenyl group, a 2-valent biphenyl group, or a 2-valent terphenyl group.
In another embodiment, L3 is a phenyl group having a valence of 3.
In one embodiment of the present specification, L4 is a direct bond, a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group.
In one embodiment of the present specification, L4 is a direct bond, a 2-to 3-valent phenyl group, or a 2-to 3-valent biphenyl group.
In one embodiment of the present specification, L4 is a direct bond, a 2-valent phenyl group, a 2-valent biphenyl group, or a 2-valent terphenyl group.
In another embodiment, L4 is a direct bond, a 3-valent phenyl group, a 3-valent biphenyl group, or a 3-valent terphenyl group.
In one embodiment of the present specification, L1, L3 and L4, which are the same or different from each other, are each independently a direct bond or selected from the following structures, and L2 is selected from the following structures.
In one embodiment of the present specification, L1, L3 and L4, which are the same or different from each other, are each independently selected from direct bonding or from the following structures, and L2 is selected from the following structures.
In one embodiment of the present specification, R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 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.
In one embodiment of the present specification, R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
In one embodiment of the present specification, R1 is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R1 is an aryl group having 6 to 20 carbon atoms, and R2 is hydrogen or deuterium.
In one embodiment of the present specification, R1 is phenyl, biphenyl, or naphthyl.
In one embodiment of the present specification, R3 is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R3 is an aryl group having 6 to 20 carbon atoms, and R4 is hydrogen or deuterium.
In one embodiment of the present specification, R3 is phenyl, biphenyl, or naphthyl.
In one embodiment of the present specification, R2 is each hydrogen or deuterium.
In one embodiment of the present specification, R4 is each hydrogen or deuterium.
In one embodiment of the present specification, R2 and R4 are the same as or different from each other, and each independently is an integer of 0 to 4, R2 is 2 or more, R2 is the same as or different from each other, and R4 is 2 or more, R4 is the same as or different from each other.
In one embodiment of the present specification, r2 is 0.
In one embodiment of the present specification, r4 is 0.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 101 or 102.
[ chemical formula 101]
[ chemical formula 102]
In the above-described chemical formulas 101 and 102,
l1, L2, R1, R2, R2, m, a1 and b1 are as defined in chemical formula 1.
In one embodiment of the present specification, the chemical formula 2 is represented by the following chemical formula 201 or 202.
[ chemical formula 201]
[ chemical formula 202]
In the above-mentioned cases 201 and 202,
l3, L4, R3, R4, R4, Ar1, a2 and b2 are as defined in chemical formula 2.
In one embodiment of the present specification, m is 0 or 1.
When m is 1, the compound of formula 1
Is a 2-valent naphthyl group, and is linked to L1 and L2 of the above chemical formula 1.
In one embodiment of the present specification, Ar1 is a 2-valent group represented by the following chemical formula a 1.
[ chemical formula A1]
In the above-described chemical formula a1,
x1 and X2 are each hydrogen, or are bonded directly to one another or via-O-or-S-,
any one of Q1 to Q16 is linked to L3 of the above chemical formula 2, and the other is linked to L4 of the above chemical formula 2, and the others are the same or different from each other, and each independently is hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, Ar1 is a 2-valent group represented by any one of the following chemical formulae a11 to a 14.
In the above chemical formulae a11 to a14, Q1 to Q16 are defined as in the chemical formula a 1.
In one embodiment of the present specification, the substituents of Q1 to Q16, which are not linked to L3 or L4 of chemical formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, the substituents of Q1 to Q16, which are not linked to L3 or L4 of chemical formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
In one embodiment of the present specification, the substituent not linked to L3 or L4 of chemical formula 2 in Q1 to Q16 is hydrogen.
In one embodiment of the present specification, Ar1 is a 2-valent group selected from the following structures.
The above structures are substituted or unsubstituted with deuterium, cyano, alkyl, aryl or heteroaryl,
In one embodiment of the present specification, Ar1 is a 2-valent group selected from the following structures.
The above structures are substituted or unsubstituted with deuterium, cyano, alkyl, aryl or heteroaryl,
In one embodiment of the present specification, a1, a2, b1 and b2 are the same as or different from each other, and are each independently an integer of 1 to 3.
In one embodiment of the present specification, a1 is 1 or 2.
In one embodiment of the present specification, a1 is 1.
In one embodiment of the present specification, a1 is 2.
In one embodiment of the present specification, a2 is 1 or 2.
In one embodiment of the present specification, a2 is 1.
In one embodiment of the present specification, a2 is 2.
In one embodiment of the present specification, chemical formula 1 is represented by chemical formula 103 or 104 below.
[ chemical formula 103]
[ chemical formula 104]
In the above-described chemical formulas 103 and 104,
r1, R2, R2, m, L2 and b1 are as defined in chemical formula 1,
l11 is a direct bond, a substituted or unsubstituted 2-valent phenyl group, or a substituted or unsubstituted 2-valent biphenyl group,
r11 and R12, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r12 is an integer of 0 to 4, and when R12 is 2 or more, R12 may be the same as or different from each other.
In one embodiment of the present specification, R11 is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R11 is phenyl.
In one embodiment of the present specification, R12 is hydrogen.
In one embodiment of the present specification, r12 is 0.
In one embodiment of the present description, L11 is a direct bond.
In one embodiment of the present specification, b1 is 1 or 2.
In one embodiment of the present specification, b1 is 1.
In one embodiment of the present specification, b1 is 2.
In one embodiment of the present specification, b2 is 1 or 2.
In one embodiment of the present specification, b2 is 1.
In one embodiment of the present specification, b2 is 2.
In one embodiment of the present specification, — L2- (CN) of the above chemical formula 1b1or-L4- (CN) of the above chemical formula 2b2Selected from the following structures.
In the above structure, L21 is a direct bond, a 2-valent phenyl group, or a 2-valent biphenyl group.
In one embodiment of the present specification, L21 is a direct bond or a 2-valent phenyl group.
In one embodiment of the present description, L21 is a direct bond.
In one embodiment of the present specification, — L2- (CN) of the above chemical formula 1b1or-L4- (CN) of the above chemical formula 2b2Selected from the following structures.
In one embodiment of the present specification, L1 is a direct bond, a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group,
l2 is a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group,
l3 and L4, which are the same or different from each other, are each independently a direct bond, or a 6 to 20-carbon-atom-number aryl group having 2 to 3 valences,
r1 is an aryl group having 6 to 20 carbon atoms, R2 is hydrogen or deuterium,
r3 is an aryl group having 6 to 20 carbon atoms, R4 is hydrogen or deuterium,
the substituent not linked to L3 or L4 of chemical formula 2 in Q1 to Q16 is hydrogen.
In one embodiment of the present specification, the heterocyclic compound represented by the above chemical formula 1 is any one selected from the following compounds.
In one embodiment of the present specification, the heterocyclic compound represented by the above chemical formula 2 is any one selected from the following compounds.
The compound according to one embodiment of the present specification can be produced by a production method described later. Substituents may be added or excluded, and the position of the substituent may be changed, as necessary. Further, the starting materials, reaction conditions, and the like may be changed based on techniques known in the art.
For example, the compound represented by the above chemical formula 1 may produce a core structure as shown in the following reaction formula 1, and the compound represented by the above chemical formula 2 may produce a core structure as shown in the following general formula 2. The substituents may be combined by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art. The substituents may be bonded as shown in the following general formulae 1 and 2, but are not limited thereto.
[ general formula 1]
[ general formula 2]
In the above formula 1, L1, L2, R1, R2, R2, m, a1, and b1 are defined as in the above formula 1, and in the above formula 2, L3, L4, Ar1, R3, R4, R4, a2, and b2 are defined as in the above formula 2. In formulas 1 and 2, X is halogen, more preferably bromine or chlorine. The above reaction is a suzuki coupling reaction, preferably in the presence of a palladium catalyst and a base, and the reactive group used for the suzuki coupling reaction can be modified according to techniques known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
The present specification provides an organic light-emitting device comprising the above-mentioned compound.
The present specification provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided 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 include a compound represented by the chemical formula 1.
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.
In the present specification, the above-mentioned "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target area. The size of the above "layer" is not limited, and the size of each "layer" may be the same or different. In one embodiment, the size of the "layer" may be equal to the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel (sub-pixel).
In the present specification, the meaning that a specific substance a is contained in a B layer is that i) the case where 1 or more substances a are contained in a B layer of one layer, and ii) the case where a B layer is composed of 1 or more layers and substances a are contained in 1 or more layers of a plurality of B layers are all included.
In the present specification, the meaning that the specific substance a is contained in the C layer or the D layer is that all cases where i) the substance a is contained in 1 or more of the 1 or more C layers, ii) the substance a is contained in 1 or more of the 1 or more D layers, or iii) the substance a is contained in the 1 or more C layers and the 1 or more D layers, respectively, are included.
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 el device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, or the like. 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 light emitting layer including a heterocyclic compound represented by the chemical formula 1.
In one embodiment of the present disclosure, the organic layer includes an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, or a hole blocking layer, and the electron injection layer, the electron transport layer, the layer that simultaneously injects and transports electrons, or the hole blocking layer includes the heterocyclic compound represented by chemical formula 1.
In one embodiment of the present specification, the electron injection layer, the electron transport layer, the layer in which electron injection and transport are simultaneously performed, or the hole blocking layer contains 1 or 2 or more types of n-type dopants selected from alkali metals and alkaline earth metals.
When the organic alkali metal compound or the organic alkaline earth metal compound is used as the n-type dopant, stability with respect to holes from the light-emitting layer can be secured, and thus the lifetime of the organic light-emitting device can be improved. In addition, the electron mobility of the electron transport layer, the proportion of the organic alkali metal compound or the organic alkaline earth metal compound are adjusted to maximize the balance of holes and electrons in the light emitting layer, and thus the light emitting efficiency can be increased.
In this specification, LiQ is more preferable as the n-type dopant used for the electron transport layer.
The electron transport layer may include the heterocyclic compound represented by chemical formula 1 and the n-type dopant at a weight ratio of 1:9 to 9: 1. Preferably, the heterocyclic compound of the above chemical formula 1 and the above n-type dopant may be contained at 2:8 to 8:2, and more preferably, may be contained at 3:7 to 7: 3.
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, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
In one embodiment of the present specification, 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 1 or more organic material layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.
In one embodiment of the present specification, the 1 or more organic layers further include 1 or more layers selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In one embodiment of the present disclosure, the second electrode is a cathode, and the second electrode is an anode.
In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present disclosure, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
For example, fig. 1 to 2 illustrate the structure of an organic light emitting device according to an embodiment of the present specification. The organic light emitting device is illustrated in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light-emitting device in which an anode 102, a light-emitting layer 106, and a cathode 108 are sequentially stacked on a substrate 101. The compound represented by the above chemical formula 1 is contained in the light emitting layer.
Fig. 2 illustrates a structure of an organic light emitting device in which an anode 102, a hole injection layer 103, a first hole transport layer 104, a second hole transport layer 105, a light emitting layer 106, an electron injection and transport layer 107, and a cathode 108 are sequentially stacked on a substrate 101. According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is included in the electron injecting and transporting layer 107.
The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light emitting layer contains the above-described 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.
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 display device is manufactured by depositing a metal, 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 (e-beam evaporation) method to form 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 device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.
In addition, the compound represented by the above chemical formula 1 may be formed into 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 cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device. However, the production method 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. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., 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 cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but 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 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 dibenzofuran derivatives and ladder furan compounds (R) ((R))
) And pyrimidine derivatives, but are not limited thereto.
In one embodiment of the present specification, an anthracene derivative substituted with deuterium can be used as a host material of the light-emitting layer.
As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, 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, perylene, and the like having an arylamine group,
Diindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine 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 hole injection layer is a layer that receives holes from the electrode. The hole injection substance is preferably as follows: a substance having an ability to transport holes, an effect of receiving holes from the anode, and an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, a substance excellent in the ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film-forming ability is preferable. Further, it is preferable that 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. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and 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. In addition, the hole transport layer may have a multi-layer structure. For example, a first hole transport layer and a second hole transport layer may be included.
The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (3), the organic radical compound, the 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. Suitable cathode substances are, in particular, the usual substances having a low work function and accompanied by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is receivingA layer of electrons from the electrode. The electron-injecting substance is preferably as follows: a substance which has an excellent ability to transport electrons, has an effect of receiving electrons from the second electrode, and has an excellent electron injection effect for the light-emitting layer or the light-emitting material. Further, a substance which prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and which has excellent thin-film-forming ability is preferable. 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 electron blocking layer is a layer that can prevent electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer, thereby improving the lifetime and efficiency of the device. Any known material may be used without limitation, and the layer may be formed between the light-emitting layer and the hole-injecting layer or between the light-emitting layer and the layer where hole injection and hole transport are performed simultaneously.
The hole blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the electron injection layer. Specifically, there are
Oxadiazole derivatives or triazolesDerivatives, phenanthroline derivatives, aluminum complexes, and the like, but are 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
Hereinafter, in order to specifically explain the present specification, the details will be explained by referring to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.
Production example 1: preparation of Compound E1
After completely dissolving the above-mentioned compound E1-A (10g, 41.5mmol) and the above-mentioned compound E1-B (19.0g, 41.5mmol) in tetrahydrofuran (200mL), potassium carbonate (17.2g, 124.6mmol) was dissolved in 60mL of water and added. Tetrakis (triphenylphosphine) palladium (1.4g, 1.25mmol) was added, followed by stirring with heating for 8 hours. Cooling to normal temperature, removing the potassium carbonate solution after the reaction is finished, and filtering the white solid. The filtered white solid was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce compound E1(17.1g, yield 77%).
MS[M+H]+＝536
Production example 2: preparation of Compound E2
A compound represented by the above chemical formula E2 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝536
Production example 3: preparation of Compound E3
A compound represented by the above chemical formula E3 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝586
Production example 4: preparation of Compound E4
A compound represented by the above chemical formula E4 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝624
Production example 5: preparation of Compound E5
A compound represented by the above chemical formula E5 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝561
Production example 6: preparation of Compound E6
A compound represented by the above chemical formula E6 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝586
Production example 7: preparation of Compound E7
A compound represented by the above chemical formula E7 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝510
Production example 8: preparation of Compound E8
A compound represented by the above chemical formula E8 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝638
Production example 9: preparation of Compound E9
A compound represented by the above chemical formula E9 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝622
Production example 10: preparation of Compound E10
A compound represented by the above chemical formula E10 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝510
Production example 11: preparation of Compound E11
A compound represented by the above chemical formula E11 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝510
Production example 12: preparation of Compound E12
A compound represented by the above chemical formula E12 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝730
Production example 13: preparation of Compound E13
A compound represented by the above chemical formula E13 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝714
Production example 14: preparation of Compound E14
A compound represented by the above chemical formula E14 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝638
Production example 15: preparation of Compound E15
A compound represented by the above chemical formula E15 was produced in the same manner as in the production method of E1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝790
Example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) 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, or 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, the following HI-A compound was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, HAT compound described below is sequentially added
And the following HT-A compounds
The first hole transport layer and the second hole transport layer are formed by vacuum evaporation.
Then, on the hole transport layer, the film thickness
The following BH compound and BD compound were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, compound E1 of production example 1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form a 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 rate of the organic material is maintained at 0.4-0.4
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 2 to 15
Organic light-emitting devices were manufactured by the same method as in example 1 above, except that compounds E2 to E15 described in table 1 below were used instead of compound E1, respectively.
Comparative examples 1 to 10
An organic light-emitting device was produced in the same manner as in mutexample 1 above, mutexcept that compounds ET-a to ET-J described in table 1 below were used instead of compound E1 in production mutexample 1.
Examples of the experiments
For the organic light emitting devices manufactured in the above examples 1 to 15 and comparative examples 1 to 10, at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time (T90) until the luminance became 90% of the initial luminance was measured at the current density of (1). The results are shown in table 1 below.
[ Table 1]
As described in table 1 above, the compound represented by chemical formula 1 or 2 according to the present invention may be used in an organic layer of an organic light emitting device that can simultaneously perform electron injection and electron transport.
Comparing the mutexamples of table 1 and comparative mutexamples 1 and 2(ET-a and ET-B), the compounds having a cyano substituent substituted on quinazoline according to chemical formula 1 or 2 of the present invention are significantly superior in efficiency of an organic light emitting device, as compared to the compounds of chemical formula 1 in which L1 or L2 is naphthylene.
Comparing the examples of table 1 and comparative examples 3 to 5(ET-C to ET-E), the compound having a cyano substituent substituted on the quinazoline as in chemical formula 1 or 2 according to the present invention is significantly superior in efficiency of the organic light emitting device, compared to the compound having a substituted arylene group as L2 of chemical formula 1.
When the examples in table 1 and comparative example 6(ET-F) are compared, the compounds having a cyano substituent substituted on the quinazoline as shown in chemical formula 1 or 2 according to the present invention are significantly superior in efficiency of the organic light emitting device as compared to the compounds having a direct bond of L1 or L2 in chemical formula 1.
Comparing the examples of table 1 and comparative examples 7 and 8(ET-G and ET-H), the compounds having a cyano substituent substituted on quinazoline according to chemical formula 1 or 2 of the present invention are significantly superior in efficiency of an organic light emitting device, compared to the structure of chemical formula 2 in which a cyano group is bonded to R3 or L3.
Comparing the examples of table 1 with comparative examples 9 and 10(ET-I and ET-J), the compounds having a cyano substituent substituted on the quinazoline as shown in chemical formula 1 or 2 according to the present invention are significantly superior in terms of the lifetime of the organic light emitting device, compared to the compounds having a cyano group not substituted on the core structure.
Claims (16)
1. A heterocyclic compound represented by the following chemical formula 1 or 2:
chemical formula 1
Chemical formula 2
Wherein, in the chemical formula 1 or 2,
l1 is a direct bond, a substituted or unsubstituted 2-to 4-valent phenyl group, a substituted or unsubstituted 2-to 4-valent biphenyl group, or a substituted or unsubstituted 2-to 4-valent terphenyl group,
l2 is a 2-to 4-valent phenyl group, a 2-to 4-valent biphenyl group, or a 2-to 4-valent terphenyl group,
l3 and L4 are identical to or different from one another and are each independently a direct bond or a substituted or unsubstituted aromatic radical having a valency of 2 to 4,
ar1 is a 2-valent group represented by the following chemical formula A1,
m is 0 or 1, and m is,
r1 to R4 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r2 and r4 are the same as or different from each other and each independently an integer of 0 to 4,
a1, a2, b1 and b2 are the same as or different from each other and each independently is an integer of 1 to 3,
when R2 is 2 or more, R2 may be the same or different from each other, and
when R4 is 2 or more, R4 may be the same or different from each other,
chemical formula A1
In the chemical formula a1, the chemical formula a,
x1 and X2 are each hydrogen, or are bonded directly to one another or via-O-or-S-, and
any one of Q1 to Q16 is linked to L3 of said chemical formula 2, and the other is linked to L4 of said chemical formula 2, and the others are the same or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 101 or 102:
chemical formula 101
Chemical formula 102
In the chemical formulae 101 and 102,
l1, L2, R1, R2, R2, m, a1 and b1 are as defined in chemical formula 1.
3. The heterocyclic compound according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 201 or 202:
chemical formula 201
Chemical formula 202
In the chemical formulas 201 and 202 as described above,
l3, L4, R3, R4, R4, Ar1, a2 and b2 are as defined in chemical formula 2.
4. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 103 or 104:
chemical formula 103
Chemical formula 104
In the chemical formulae 103 and 104,
r1, R2, R2, m, L2 and b1 are as defined in chemical formula 1,
l11 is a direct bond, a substituted or unsubstituted 2-valent phenyl group, or a substituted or unsubstituted 2-valent biphenyl group,
r11 and R12 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and
r12 is an integer of 0 to 4, and R12 is 2 or more, R12 are the same as or different from each other.
5. The heterocyclic compound according to claim 1, wherein Ar1 is a 2-valent group selected from the following structures:
said structure being substituted or unsubstituted with deuterium, cyano, alkyl, aryl, or heteroaryl, and
is a position to which L3 or L4 of chemical formula 2 is attached.
6. The heterocyclic compound according to claim 1, wherein-L2- (CN) of the chemical formula 1b1or-L4- (CN) of the chemical formula 2b2Selected from the following structures:
in the structure, L21 is a direct bond, a 2-valent phenyl group, or a 2-valent biphenyl group.
7. The heterocyclic compound according to claim 1, wherein L1, L3 and L4 are the same or different from each other and are each independently a direct bond or selected from the following structures, and L2 is selected from the following structures:
8. the heterocyclic compound according to claim 1, wherein R1 is an aryl group having 6 to 20 carbon atoms, and R2 is hydrogen or deuterium.
9. The heterocyclic compound according to claim 1, wherein R3 is an aryl group having 6 to 20 carbon atoms, and R4 is hydrogen or deuterium.
10. The heterocyclic compound according to claim 1, wherein L1 is a direct bond, a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group,
l2 is a 2-to 3-valent phenyl group, a 2-to 3-valent biphenyl group, or a 2-to 3-valent terphenyl group,
l3 and L4 are the same as or different from each other, and are each independently a direct bond, or a 6 to 20-carbon-atom-number aryl group having 2 to 3 valences,
r1 is an aryl group having 6 to 20 carbon atoms, and R2 is hydrogen or deuterium,
r3 is an aryl group having 6 to 20 carbon atoms, and R4 is hydrogen or deuterium, and
the substituent not linked to L3 or L4 of chemical formula 2 in Q1 to Q16 is hydrogen.
11. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by the chemical formula 1 is any one selected from the group consisting of:
12. the heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by the chemical formula 2 is any one selected from the group consisting of:
13. 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 heterocyclic compound according to any one of claims 1 to 12.
14. The organic light-emitting device according to claim 13, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer contains the heterocyclic compound.
15. The organic light-emitting device according to claim 13, wherein the organic layer comprises an electron injection layer, an electron transport layer, a layer that performs electron injection and transport simultaneously, or a hole blocking layer, and the electron injection layer, the electron transport layer, the layer that performs electron injection and transport simultaneously, or the hole blocking layer contains the heterocyclic compound.
16. The organic light-emitting device according to claim 15, wherein the electron injection layer, the electron transport layer, the layer simultaneously performing electron injection and transport, or the hole blocking layer contains 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.
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| WO2013162148A1 (en) * | 2012-04-24 | 2013-10-31 | 제일모직 주식회사 | Compound for organic optoelectric device, organic light emitting device containing same, and display device containing said organic light emitting device |
| CN107848989A (en) * | 2016-07-20 | 2018-03-27 | 株式会社Lg化学 | Novel heterocyclic compound and the organic luminescent device for including it |
| CN108063188A (en) * | 2016-11-08 | 2018-05-22 | 株式会社Lg化学 | Organic illuminating element |
| KR20180131482A (en) * | 2017-05-31 | 2018-12-10 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN109111398A (en) * | 2018-09-30 | 2019-01-01 | 长春海谱润斯科技有限公司 | A kind of heterocyclic compound and its organic electroluminescence device |
| CN109476678A (en) * | 2017-02-14 | 2019-03-15 | 株式会社Lg化学 | Heterocyclic compound and organic illuminating element comprising it |
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| KR102572294B1 (en) * | 2015-09-25 | 2023-08-30 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| WO2013162148A1 (en) * | 2012-04-24 | 2013-10-31 | 제일모직 주식회사 | Compound for organic optoelectric device, organic light emitting device containing same, and display device containing said organic light emitting device |
| CN107848989A (en) * | 2016-07-20 | 2018-03-27 | 株式会社Lg化学 | Novel heterocyclic compound and the organic luminescent device for including it |
| CN108063188A (en) * | 2016-11-08 | 2018-05-22 | 株式会社Lg化学 | Organic illuminating element |
| CN109476678A (en) * | 2017-02-14 | 2019-03-15 | 株式会社Lg化学 | Heterocyclic compound and organic illuminating element comprising it |
| KR20180131482A (en) * | 2017-05-31 | 2018-12-10 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN109111398A (en) * | 2018-09-30 | 2019-01-01 | 长春海谱润斯科技有限公司 | A kind of heterocyclic compound and its organic electroluminescence device |
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