CN109415375B - Heterocyclic compound and organic light-emitting element comprising same - Google Patents
Heterocyclic compound and organic light-emitting element comprising same Download PDFInfo
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- CN109415375B CN109415375B CN201780041153.2A CN201780041153A CN109415375B CN 109415375 B CN109415375 B CN 109415375B CN 201780041153 A CN201780041153 A CN 201780041153A CN 109415375 B CN109415375 B CN 109415375B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 76
- 239000010410 layer Substances 0.000 claims description 155
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000012044 organic layer Substances 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 38
- 239000007924 injection Substances 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 35
- 229910052805 deuterium Inorganic materials 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 230000005525 hole transport Effects 0.000 claims description 20
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 15
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
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- 125000005264 aryl amine group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
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- 125000005110 aryl thio group Chemical group 0.000 claims description 9
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- -1 nitro, hydroxyl Chemical group 0.000 description 112
- 125000004432 carbon atom Chemical group C* 0.000 description 104
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 57
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 20
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 9
- 125000001769 aryl amino group Chemical group 0.000 description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 9
- 125000005493 quinolyl group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 8
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 125000004653 anthracenylene group Chemical group 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 125000004957 naphthylene group Chemical group 0.000 description 6
- 125000006836 terphenylene group Chemical group 0.000 description 6
- 125000005556 thienylene group Chemical group 0.000 description 6
- 125000004306 triazinyl group Chemical group 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 5
- 125000005956 isoquinolyl group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 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
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Abstract
The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting element including the same.
Description
Technical Field
This application claims priority to korean patent application No. 10-2016-.
The present specification relates to a heterocyclic compound and an organic light-emitting element including the same.
Background
The organic light emitting phenomenon is one example of conversion of current into visible light through an internal process of a specific organic molecule. The principle of the organic light emitting phenomenon is as follows. When an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer are recombined to form excitons (exiton), which are re-transitioned to the ground state to emit light. An organic light-emitting element utilizing such a principle may generally be composed of a cathode and an anode, and an organic layer including, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like, located therebetween.
In order to improve the performance, lifetime, or efficiency of organic light emitting elements, development of organic thin film materials is continuously demanded.
Disclosure of Invention
The present specification provides a heterocyclic compound and an organic light-emitting element including the same.
One embodiment of the present specification provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above,
r5 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, nitro, hydroxyl, aryloxy, alkylthio(s) ((R))
Alkyl thio), arylthio(s) ((R)
Aryl thio), alkyl sulfoxide group(s) ((s)
Alkyl sulfonyl), aryl sulfoxide group(s) ((s)
Aryl sufoxy), silyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted Aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted alkylamino, substituted or unsubstituted aralkylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted arylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted arylphosphino, or substituted or unsubstituted heterocyclic group,
l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
ar1 is a substituted or unsubstituted heterocyclic group,
r1 to R4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
a and b are each an integer of 0 to 4,
c is an integer of 0 to 3,
d is an integer of 0 to 5,
when a to d are each 2 or more, the substituents in parentheses may be the same or different from each other,
n1 and n2 are 0 or 1,
1 or more of n1 and n2 are integers of 1,
x1 and X2 are hydrogen or are directly bonded to each other.
In addition, one embodiment of the present specification provides an organic light-emitting element including: the organic light-emitting device includes a first electrode, a second electrode, and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers include the heterocyclic compound.
The compound described in this specification can be used as a material for an organic layer of an organic light-emitting element. The compound according to at least one embodiment can achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting element. The compound described in the present specification can be used as a hole injection material, a hole transport material, an electron suppression material, a light emission material, a hole suppression material, an electron transport material, or an electron injection material.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4.
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
Detailed Description
The present specification will be described in more detail below.
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above,
r5 to R8 are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
ar1 is a substituted or unsubstituted heterocyclic group,
r1 to R4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
a and b are each an integer of 0 to 4,
c is an integer of 0 to 3,
d is an integer of 0 to 5,
when a to d are each 2 or more, the substituents in parentheses may be the same or different from each other,
n1 and n2 are 0 or 1,
1 or more of n1 and n2 are integers of 1,
x1 and X2 are hydrogen or are directly bonded to each other.
The following are examples of the above-mentioned substituent, but the present invention is not limited thereto.
In the present specification, 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 substituted position 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.
The term "substituted or unsubstituted" in the present specification means that the substituent is substituted with 1 or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are bonded" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, or a substituent sterically closest to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring are considered to be "adjacent" groups to each other.
In this specification, the expressions "and
refers to a site bound to chemical formula 1 or a core structure.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the silyl group may be represented by-SiRaRbRcThe above chemical formula (II) representsa、RbAnd RcEach may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In this specification, the boron group may be represented by-BRaRbThe above chemical formula (II) representsaAnd RbEach may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
In the present specification, the alkyl group may be linear or branched, the number of carbon atoms is not particularly limited, and may be 1 to 50, and according to one embodiment, the number of carbon atoms may be 1 to 30, and according to another embodiment, the number of carbon atoms may be 1 to 20. 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, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, and the number of carbon atoms may be 3 to 60, according to one embodiment, 3 to 30, and according to another embodiment, 3 to 20. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, and the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, the amine group may be selected from-NH2Alkylamino, N-arylalkylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino radicals, carbogenThe number of subunits is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, and a triphenylamino group.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, and is preferably 2 to 40. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, styryl and the like.
In the present specification, the number of carbon atoms of the alkylamino group is not particularly limited, and may be 1 to 40, according to one embodiment, the number of carbon atoms may be 1 to 30, and according to another embodiment, the number of carbon atoms may be 1 to 20. Specific examples of the alkylamino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, and a triphenylamino group.
In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.
Specific examples of the arylamine group include a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 3-methyl-phenylamino group, a 4-methyl-naphthylamino group, a 2-methyl-biphenylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, and a triphenylamino group, but the present invention is not limited thereto.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. The heteroaryl group in the heteroarylamino group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group containing 2 or more heteroaryls may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group.
In the present specification, arylheteroarylamino refers to an amino group substituted with an aryl group and a heteroaryl group.
In the present specification, as an example of the arylphosphino group, there is a substituted or unsubstituted monoarylphosphino group, a substituted or unsubstituted diarylphosphino group, or a substituted or unsubstituted triarylphosphino group. The aryl group in the above-mentioned arylphosphino group may be a monocyclic aryl group or a polycyclic aryl group. The above-mentioned arylphosphino group containing 2 or more aryl groups may be a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, and the number of carbon atoms may be 6 to 60, 6 to 30 according to one embodiment, and 6 to 20 according to another embodiment. Specific examples of the monocyclic aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, and the like.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, and may be 10 to 60, 10 to 30 according to one embodiment, and 10 to 20 according to another embodiment. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, the heterocyclic group contains 1 or more heteroatoms other than carbon atoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but the number of carbon atoms may be 2 to 60. According to one embodiment, the number of carbon atoms may be 2 to 30. According to another embodiment, the number of carbon atoms may be from 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzoquinolinyl, pyridazinyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phen)anthracoline), thiazolyl, isothiazolyl
Azolyl group,
Examples of the organic group include, but are not limited to, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, a benzimidazolaphthyl group, a phenanthroimidazoimidazolyl group, and a benzimidazolphenanthridinyl group.
The heterocyclic group may be monocyclic or polycyclic, or may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.
In the present specification, the hydrocarbon ring may be an aliphatic, aromatic, or condensed ring of an aliphatic and an aromatic, and the hydrocarbon ring may be selected from the cycloalkyl group and the aryl group, except that the hydrocarbon ring has a valence of 1. The heterocyclic group may be aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, and may be selected from the examples of the heterocyclic group except that it has a valence of 1.
In the present specification, the aryl group in the aryloxy group, arylthio group, arylsulfoxide group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group, arylheteroarylamino group can be applied to the aryl group described above.
In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxide group, the arylalkyl group, the aralkylamino group, the alkylaryl group, and the alkylamino group can be applied to the above description of the alkyl group.
In the present specification, the heteroaryl group in the heteroaryl group, heteroarylamino group and arylheteroarylamino group can be applied to the above-mentioned description of the heterocyclic group.
In the present specification, the alkenyl group in the aralkenyl group and the arylalkenyl group can be applied to the above-mentioned description of the alkenyl group.
In the present specification, the alkyl group in the arylalkyl group and the thioalkyl group can be applied to the above description of the alkyl group.
In the present specification, the aryl group can be applied to the above description of the aryl group, except that the arylene group has a valence of 2.
In the present specification, the heteroaryl group can be used in addition to the 2-valent group.
In one embodiment of the present specification, X1 and X2 are both hydrogen.
In another embodiment, the above X1 and X2 are directly bonded to each other to form a five-membered ring.
In one embodiment of the present specification, n1 and n2 are 0 or 1, and 1 or more of n1 and n2 are integers of 1.
According to another embodiment, n1 and n2 are integers of 1.
In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
In one embodiment of the present disclosure, Ar1-L2-NR3R4 has one of the following structures.
In the above-described structure, the first and second electrodes,
l2, R3 and R4 are as defined in the above chemical formula 1,
r 'and R' are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
the above structures may be further substituted.
In one embodiment of the present specification, the above R' and R ″ are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, the above R' and R ″ are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R' and R ″ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
In one embodiment of the present specification, R' and R ″ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
In another embodiment, the above R' and R "are the same or different from each other and each independently is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
According to another embodiment, R' and R "are the same or different from each other and are each independently a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted tert-butyl group.
In another embodiment, R' and R "are the same or different from each other and are each independently methyl, ethyl or tert-butyl.
According to an embodiment of the present specification, the heterocyclic compound represented by the above chemical formula 1 may be any one selected from the following chemical formulas 1-a to 1-D.
[ chemical formula 1-A ]
[ chemical formula 1-B ]
[ chemical formula 1-C ]
[ chemical formula 1-D ]
In the above chemical formulas 1-A to 1-D,
x1, X2, R1 to R8, L1, L2, n1 and n2 are the same as defined in the above chemical formula 1,
w1 to W4, equal to or different from each other, are each independently O, S or SiT1T2,
t1, T2, R101 to R104, equal to or different from each other, are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
s1 and s3 are each an integer of 0 to 5,
s2 and s4 are each an integer of 0 to 7,
when s1 to s4 are each an integer of 2 or more, the substituents in parentheses may be the same or different from each other.
According to an embodiment of the present specification, s1 is 0 or 1.
According to an embodiment of the present specification, s2 is 0 or 1.
According to an embodiment of the present specification, s3 is 0 or 1.
According to an embodiment of the present specification, s4 is 0 or 1.
In another embodiment, T1 and T2 are the same or different from each other and are each independently hydrogen or substituted or unsubstituted alkyl.
According to another embodiment, T1 and T2 are the same as or different from each other, and each is independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.
In another embodiment, T1 and T2 which may be the same or different from each other, are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
According to another embodiment, T1 and T2 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted T-butyl group.
In another embodiment, the T1 and T2 are methyl.
In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to another embodiment, R101 to R104 are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, R101 to R104 are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, R101 to R104 are hydrogen.
In one embodiment of the present specification, R5 to R8 are the same or different and each independently hydrogen, deuterium, a halogen group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R5 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
In another embodiment, R5 to R8 which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
According to another embodiment, the above R5 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.
In another embodiment, R5 to R8 are the same or different and are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl, phenyl, biphenyl, naphthyl, or dibenzofuranyl.
According to another embodiment, R5 and R8 are hydrogen.
In one embodiment of the present specification, L1 and L2, which may be the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 30 carbon atoms.
In another embodiment, each of L1 and L2, which are the same as or different from each other, is independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted furylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazolyl group.
According to another embodiment, L1 and L2, which are the same as or different from each other, are each independently a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a9, 9-diphenylfluorenyl group, a9, 9-dimethylfluorenyl group, a phenanthrylene group, an anthracenylene group, a triphenylene group, a thienylene group, a furanylene group, a pyrrolylene group substituted with a methyl group or a phenyl group or unsubstituted, a dibenzofuranylene group, a dibenzothiophenylene group, a carbazolyl group substituted with an ethyl group or a phenyl group or unsubstituted.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or one of the following structures.
In one embodiment of the present specification, L1 and L2 are directly bonded to each other.
In one embodiment of the present specification, R1 to R4 are the same or different and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present specification, R1 to R4 are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In another embodiment, R1 to R4 which may be the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to another embodiment, R1 to R4 which may be the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to another embodiment, R1 to R4 are the same as or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthryl group
A phenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted,Substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzofuranyl
An azole group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted fluorenylbenzofuranyl group, or a substituted or unsubstituted benzofurodibenzofuranyl group.
In one embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each is independently one selected from the following structures.
In the above-described structure, the first and second electrodes,
r201 to R297 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a silyl group, a boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
a1, a6, a10, a23 and a25 are integers of 0 to 5, respectively,
a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are respectively integers of 0 to 4,
a3 and a22 are each an integer of 0 to 7,
a4, a7, a12, a15, a19, a26 and a27 are integers of 0 to 3, respectively,
a11 is an integer from 0 to 9,
a13, a20 and a24 are integers of 0 to 6,
a18, b5, b10, b14 and b16 are integers of 0 to 2, respectively,
in the case where a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other,
when a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15, b17 to b32, a3, a22, a4, a7, a12, a15, a19, a26, a27, a11, a13, a20, and a24 are respectively 2 or more, the substituents in parentheses are the same as or different from each other.
In one embodiment of the present specification, R201 to R297 are the same or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a silyl group substituted or unsubstituted with an alkyl group, an alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted, a cycloalkyl group having 3 to 20 carbon atoms which is substituted or unsubstituted, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted.
According to another embodiment, the above R201 to R297 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a silyl group substituted with a methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group.
In another embodiment, R201 to R297 are the same or different from each other and are each independently hydrogen, deuterium, fluorine (F), trimethylsilyl, methyl, tert-butyl, phenyl, or biphenyl.
In one embodiment of the present disclosure, the a1 to a35 and the b1 to b32 are integers of 0 to 2, respectively.
In one embodiment of the present specification, R1 to R4, which may be the same or different from each other, are each independently a phenyl group substituted or unsubstituted with fluorine (-F), a methyl group, a tert-butyl group or a trimethylsilyl group; 9, 9-dimethylfluorenyl; a naphthyl group; or a dibenzofuranyl group.
According to an embodiment of the specification, the heterocyclic compound of chemical formula 1 may be any one selected from the following heterocyclic compounds.
The compound according to one embodiment of the present specification can be produced by a production method described later. For example, the compound of chemical formula 1 can be produced into a core structure as in the production example described below. The substituents may be bonded 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.
According to an embodiment of the present specification, there can be provided an organic light-emitting element including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the heterocyclic compound.
According to one embodiment of the present description, the organic layer of the organic light-emitting device of the present description may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and fewer or more organic layers may be included.
The organic light emitting device structure of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates an example of the structure of an organic light-emitting element in which an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In this structure, the above compound may be contained in the above light-emitting layer 3.
Fig. 2 illustrates an example of the structure of an organic light-emitting element in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4 are stacked in this order on a substrate 1. In such a structure, the above compound may be contained in the above hole injection layer 5, hole transport layer 6, light emitting layer 3, or electron transport layer 7.
According to one embodiment of the present disclosure, the organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes a heterocyclic compound represented by the chemical formula 1.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the chemical formula 1.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes a heterocyclic compound represented by the chemical formula 1, and the light emitting layer further includes a compound represented by the chemical formula 2.
[ chemical formula 2]
In the above-described chemical formula 2,
r9 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkyl amine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
p is an integer of 0 to 6,
when p is 2 or more, the substituents in parentheses may be the same or different from each other,
l3 to L6, which are identical to or different from one another, are each independently a direct bond, or a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar2 to Ar5, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to one embodiment of the present disclosure, R9 is hydrogen, deuterium, a halogen group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R9 is the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R9 each represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, which may be the same or different from each other.
In one embodiment of the present specification, R9 each represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
According to another embodiment, R9 is hydrogen.
In one embodiment of the present specification, p is 0 or 1.
In one embodiment of the present specification, L3 to L6 may be the same or different and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
In one embodiment of the present specification, L3 to L6, which may be the same or different, each independently represent a direct bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
According to another embodiment, the above L3 to L6, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted carbazolyl group.
In another embodiment, L3 to L6 which are the same as or different from each other, are each independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, a triphenylene group, a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group, a thienylene group, a furanylene group, a dibenzothiophenylene group, a dibenzofuranylene group, or a carbazolyl group substituted or unsubstituted with an ethyl group or a phenyl group.
According to another embodiment, the above L3 to L6, which are the same or different from each other, are each independently a direct bond or may be selected from the following structures.
According to one embodiment of the present description, L3 is a direct bond.
According to an embodiment of the present description, L4 is phenylene.
According to one embodiment of the present description, L5 and L6 are directly bonded.
In one embodiment of the present specification, Ar2 to Ar5, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to another embodiment, Ar2 to Ar5 which are the same as or different from each other, are each independently hydrogen, an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, Ar2 to Ar5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl groupOr unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoquinonyl
An azole group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted dihydroacridinyl group, a substituted or unsubstituted xanthenyl group, or a substituted or unsubstituted dibenzothiazolyl group.
According to another embodiment, Ar2 to Ar5 are the same as or different from each other, and are each independently hydrogen, phenyl, biphenyl, aryl-substituted or unsubstituted naphthyl, phenanthryl, anthracenyl, triphenylenyl, aryl-substituted or unsubstituted dibenzofuranyl, naphthobenzofuranyl, aryl-substituted or unsubstituted dibenzothiophenyl, alkyl-or aryl-substituted or unsubstituted carbazolyl, alkyl-or aryl-substituted or unsubstituted fluorenyl, aryl-substituted or unsubstituted thienyl, aryl-substituted or unsubstituted furanyl, benzothiophenyl, benzofuranyl, alkyl-or aryl-substituted or unsubstituted benzocarbazolyl, alkyl-or aryl-substituted or unsubstituted benzofluorenyl, indolocarbazolyl, pyridyl, aryl-substituted or unsubstituted isoquinolyl, quinolyl, aryl-substituted or unsubstituted quinazolinyl, quinolyl, and quinoxalinyl, Triazinyl substituted or unsubstituted by aryl, benzimidazolyl substituted or unsubstituted by aryl, benzo substituted or unsubstituted by aryl
Azolyl, benzothiazolyl substituted or unsubstituted by aryl, dihydroacridinyl substituted or unsubstituted by alkyl or aryl, xanthenyl substituted or unsubstituted by alkyl or aryl, or substituted by alkyl or arylA substituted or unsubstituted dibenzosilole group.
In another embodiment, Ar2 to Ar5 are the same or different from each other, and are each independently hydrogen; a phenyl group; a biphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; an anthracene group; a triphenylene group; dibenzofuranyl substituted or unsubstituted with phenyl; naphthobenzofuranyl; dibenzothienyl substituted or unsubstituted with phenyl; carbazolyl substituted or unsubstituted with methyl, ethyl or phenyl; fluorenyl substituted or unsubstituted with methyl or phenyl; thienyl substituted or unsubstituted with phenyl; furyl substituted or unsubstituted with phenyl; benzothienyl; a benzofuranyl group; benzocarbazolyl substituted or unsubstituted with methyl or phenyl; benzofluorenyl substituted or unsubstituted with methyl or phenyl; indolocarbazolyl; pyridyl substituted or unsubstituted with phenyl or naphthyl; isoquinolinyl substituted or unsubstituted with phenyl; a quinolyl group; a quinazolinyl group substituted or unsubstituted with a phenyl group; a triazinyl group substituted or unsubstituted with a phenyl group; benzimidazolyl substituted or unsubstituted with phenyl; benzo substituted or unsubstituted by phenyl
An azole group; a benzothiazolyl group substituted or unsubstituted with a phenyl group; a dihydroacridinyl group substituted or unsubstituted by a methyl or phenyl group; xanthyl substituted or unsubstituted with methyl or phenyl; or a dibenzosilole radical which is unsubstituted or substituted by methyl or phenyl.
In one embodiment of the present disclosure, Ar2 to Ar5 are the same or different and each independently hydrogen or selected from the following structures.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes a heterocyclic compound represented by the chemical formula 1, and the light emitting layer further includes a compound represented by the chemical formula 3.
[ chemical formula 3]
In the chemical formula 3 above, the first and second,
r10 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkyl amine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
q is an integer of 0 to 7,
when q is 2 or more, the substituents in parentheses may be the same or different from each other,
l7 to L9, which are identical to or different from one another, are each independently a direct bond, or a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar6 to Ar8, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, R10 is hydrogen, deuterium, a halogen group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R10 is the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R10 each represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, which may be the same or different from each other.
In one embodiment of the present specification, R10 represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
In another embodiment, R10 is hydrogen.
In one embodiment of the present specification, q is 0 or 1.
In one embodiment of the present specification, L7 to L9 may be the same or different and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
In one embodiment of the present specification, L7 to L9, which may be the same or different, each independently represent a direct bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
According to another embodiment, the above L7 to L9, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted carbazolyl group.
In another embodiment, L7 to L9 which are the same as or different from each other, are each independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, a triphenylene group, a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group, a thienylene group, a furanylene group, a dibenzothiophenylene group, a dibenzofuranylene group, or a carbazolyl group substituted or unsubstituted with an ethyl group or a phenyl group.
According to another embodiment, the L7 to L9 are the same or different from each other, and each is independently a direct bond, or selected from the following structures.
In one embodiment of the present disclosure, L7 to L9 are directly bonded.
In one embodiment of the present specification, Ar6 to Ar8, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to another embodiment, Ar6 to Ar8 which are the same as or different from each other, are each independently an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, Ar6 through Ar8 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstitutedSubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzimidazolyl, Substituted or unsubstituted benzo
An azole group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted dihydroacridinyl group, a substituted or unsubstituted xanthenyl group, or a substituted or unsubstituted dibenzothiazolyl group.
According to another embodiment, Ar6 to Ar8 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a naphthyl group substituted or unsubstituted with an aryl group, a phenanthryl group, an anthryl group, a triphenylene group, a dibenzofuranyl group substituted or unsubstituted with an aryl group, a naphthobenzofuranyl group, a dibenzothiophenyl group substituted or unsubstituted with an aryl group, a carbazolyl group substituted or unsubstituted with an alkyl group or an aryl group, a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group, a thienyl group substituted or unsubstituted with an aryl group, a furanyl group substituted or unsubstituted with an aryl group, a benzothiophenyl group, a benzofuranyl group, a benzocarbazolyl group substituted or unsubstituted with an alkyl group or an aryl group, a benzofluorenyl group substituted or unsubstituted with an alkyl group, an indolocarbazolyl group, a pyridyl group, an isoquinolyl group substituted or unsubstituted with an aryl group, a quinolyl group, an quinazolinyl group substituted or unsubstituted with an aryl group, Benzimidazolyl substituted or unsubstituted by aryl, benzo substituted or unsubstituted by aryl
An azole group, a benzothiazolyl group substituted or unsubstituted with an aryl group, a dihydroacridinyl group substituted or unsubstituted with an alkyl group or an aryl group, a xanthenyl group substituted or unsubstituted with an alkyl group or an aryl group, or a dibenzothiazolyl group substituted or unsubstituted with an alkyl group or an aryl group.
In another embodiment, Ar6 to Ar8 are the same or different from each other and are each independently phenyl; a biphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; an anthracene group; a triphenylene group; dibenzofuranyl substituted or unsubstituted with phenyl; naphthobenzofuranyl; dibenzothienyl substituted or unsubstituted with phenyl; carbazolyl substituted or unsubstituted with methyl, ethyl or phenyl; fluorenyl substituted or unsubstituted with methyl or phenyl; thienyl substituted or unsubstituted with phenyl; furyl substituted or unsubstituted with phenyl; benzothienyl; a benzofuranyl group; benzocarbazolyl substituted or unsubstituted with methyl or phenyl; benzofluorenyl substituted or unsubstituted with methyl or phenyl; indolocarbazolyl; pyridyl substituted or unsubstituted with phenyl or naphthyl; isoquinolinyl substituted or unsubstituted with phenyl; a quinolyl group; a quinazolinyl group substituted or unsubstituted with a phenyl group; a triazinyl group substituted or unsubstituted with a phenyl group; benzimidazolyl substituted or unsubstituted with phenyl; benzo substituted or unsubstituted by phenyl
An azole group; a benzothiazolyl group substituted or unsubstituted with a phenyl group; a dihydroacridinyl group substituted or unsubstituted by a methyl or phenyl group; xanthyl substituted or unsubstituted with methyl or phenyl; or a dibenzosilole radical which is unsubstituted or substituted by methyl or phenyl.
In one embodiment of the present disclosure, Ar6 to Ar8 are the same or different and each is independently selected from the following structures.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a host material of the light emitting layer.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a dopant of the light emitting layer.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a dopant of the light emitting layer, and the compound represented by the chemical formula 2 or the chemical formula 3 as a host material of the light emitting layer.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound represented by the chemical formula 1 as a dopant of the light emitting layer, the compound represented by the chemical formula 2 or 3 as a host material of the light emitting layer, and the heterocyclic compound represented by the chemical formula 1 may be doped at 2 to 10 wt%.
According to one embodiment of the present disclosure, the organic layer includes a hole blocking layer, an electron transporting layer, or an electron injecting layer, and the hole blocking layer, the electron transporting layer, or the electron injecting layer includes a heterocyclic compound represented by the chemical formula 1.
According to an embodiment of the present disclosure, the organic layer may further include 1 or more layers selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
An organic light-emitting element according to an embodiment of the present specification includes: the light-emitting device includes a first electrode, a second electrode, and a light-emitting layer between the first electrode and the second electrode, wherein the light-emitting layer includes a heterocyclic compound represented by the chemical formula 1.
According to another embodiment, an organic light-emitting element of the present invention includes: the light-emitting device includes a first electrode, a second electrode, and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a dopant, and may further include a host material.
In another embodiment, an organic light-emitting element of the present invention includes: the light-emitting device includes a first electrode, a second electrode, and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a dopant, and may further include a host material, and the host material may be a compound represented by the chemical formula 2 or 3. The organic light-emitting element may further include 1 or more organic layers selected from a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer in addition to the light-emitting layer. However, the structure of the organic light emitting element is not limited thereto.
According to another embodiment, an organic light-emitting element of the present invention includes: the organic light emitting device may include a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, wherein 1 or more organic layers selected from a hole injection layer and a hole transport layer may be included between the first electrode and the light emitting layer, and 1 or more organic layers selected from an electron transport layer and an electron injection layer may be included between the second electrode and the light emitting layer. However, the structure of the organic light emitting element of the present invention is not limited thereto.
In another embodiment, an organic light-emitting element of the present invention includes: the organic light emitting device may include a first electrode, a second electrode, and a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a host material, 1 or more organic layers selected from a hole injection layer and a hole transport layer may be included between the first electrode and the light emitting layer, and 1 or more organic layers selected from an electron transport layer and an electron injection layer may be included between the second electrode and the light emitting layer. However, the structure of the organic light emitting element of the present invention is not limited thereto.
According to another embodiment, an organic light-emitting element of the present invention includes: the light emitting device may include a first electrode, a second electrode, and a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a dopant, includes a compound represented by the chemical formula 2 or 3 as a host material of the light emitting layer, may include 1 or more organic layers selected from a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and may include 1 or more organic layers selected from an electron transport layer and an electron injection layer between the second electrode and the light emitting layer. However, the structure of the organic light emitting element of the present invention is not limited thereto.
In the organic light-emitting device of the present specification, 1 or more of the organic layers may be produced from a material and a method known in the art, except that the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above chemical formula 1 is contained.
When the organic light emitting element 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 element of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following method can be used: a first electrode is formed by depositing 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 (e-beam evaporation) method, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and a substance which can be used as a second electrode is deposited on the organic layer. In addition to the above method, the second electrode material, the organic layer material, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light-emitting element. In addition, regarding the heterocyclic compound represented by the above chemical formula 1, in the manufacture of the organic light emitting element, the 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.
According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment of the present disclosure, the first electrode is a cathode, and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. As specific examples of the anode material which can be used in the present invention, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SnO2A combination of a metal such as Sb and an oxide; such as 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. As specific examples of the cathode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; such as LiF/Al or LiO2Multilayer structure materials such as/Al, Mg/Ag, etc., 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 injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting species is between the work function of the anode species 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 the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having a high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; a poly (p-phenylene vinyl) (PPV) polymer; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing 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 carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
And pyrimidine derivatives, but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styrene 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 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 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 material is a material that can receive electrons from the cathode well and transfer the electrons to the light emitting layer, and a material having a high electron mobility is preferable. 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. 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, which are 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 electron transporting ability, electron injecting effect from cathode, and electron beam pairExcellent electron injection effect in the light-emitting layer or the light-emitting material, prevention of transfer of excitons generated in the light-emitting layer to the hole-injecting layer, and excellent film-forming performance. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,
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 organic light-emitting element according to the present specification may be of a top emission type, a bottom emission type, or a bidirectional emission type depending on a material used.
Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments described in the present specification may be modified into other various forms, and the scope of the present specification should not be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.
< Synthesis example >
Synthesis example 1 Synthesis of intermediate 1-a
Intermediate 1-a was synthesized according to the following reaction formula 1.
< reaction formula 1>
After 2-bromo-5-chlorobenzaldehyde (20.0g,74mmol) and 4-dibenzofuranylboronic acid (17.3g,82mmol) were completely dissolved in 300mL of tetrahydrofuran, 100mL of an aqueous potassium carbonate solution (30.7g,222mmol) was added, and tetrakis (triphenylphosphine) palladium (0.86g,0.74mmol) was added, followed by stirring under reflux for 24 hours. After completion of the reaction, the temperature was lowered to normal temperature, and then the organic layer was separated by extraction with water and ethyl acetate. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate to give < intermediate 1-a > (21.7g, 82%).
MS[M+]＝356.06
Synthesis example 2 Synthesis of intermediate 1-b
Intermediates 1-b were synthesized according to the following reaction scheme 2.
< reaction formula 2>
After < intermediate 1-a > (20.0g,56mmol) was dissolved in 300mL of tetrahydrofuran, sodium hypochlorite (5.6g,62mmol) and sulfamic acid (8.2g,84mmol) were diluted with water (50 mL each) and added, followed by stirring with heating for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, and the organic layer was separated by extraction with water and ethyl acetate. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give < intermediate 1-b > (18.8g, 90%).
MS[M+]＝372.80
Synthesis example 3 Synthesis of intermediates 1-c
Intermediates 1-c were synthesized according to the following reaction scheme 3.
< reaction formula 3>
< intermediate 1-b > (18.0g,48mmol) and 250mL of methanesulfonic acid were added, and the mixture was stirred at 80 ℃ for 9 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then the mixture is slowly dripped into water to generate solid. The resulting solid was washed with water and ethanol to give < intermediate 1-c > (16.2g, 95%).
MS[M+]＝354.79
Synthesis example 4 Synthesis of intermediates 1-d
Intermediates 1-d were synthesized according to reaction 4 below.
< reaction formula 4>
After < intermediate 1-c > (10.0g,28.1mmol) was added to 300mL of dichloromethane and stirred, bromine (6.76g,42.3mmol) diluted in 50mL of dichloromethane was slowly dropped, and then stirred at room temperature for 48 hours. Then, the resulting solid was filtered, and washed with dichloromethane and hexane. The solid was recrystallized from toluene and hexane to give < intermediate 1-d > (7.92g, 65%).
MS[M+]＝433.69
Synthesis example 5 Synthesis of intermediates 1-e
Intermediates 1-e were synthesized according to the following reaction scheme 5.
< reaction formula 5>
Under a nitrogen atmosphere, 9- (2-bromophenyl) -9H-carbazole (6.13g,19.0mmol) and 150mL of tetrahydrofuran were added and cooled to-78 ℃. To the cooled reaction solution, n-butyllithium (7.60mL,19.0mmol) was added dropwise, followed by stirring for 1 hour. Then, < intermediate 1-d > (7.50g,17.3mmol) was added thereto, and stirred at room temperature. After completion of the reaction, saturated sodium bicarbonate was added to complete the reaction, followed by extraction with ethyl acetate and water. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give < intermediate 1-e > (8.31g, 71%).
Synthesis example 6 Synthesis of intermediates 1 to f
Intermediates 1-f were synthesized according to the following reaction scheme 6.
< reaction formula 6>
To < intermediate 1-e > (8.00g,11.8mmol) and acetic acid (100mL) was added 2 drops of sulfuric acid, and the mixture was stirred with heating for 3 hours. After the reaction was complete, the solid was filtered, washed with water and ethanol, and then recrystallized from ethyl acetate and hexane to give < intermediate 1-f > (7.40g, 95%).
MS[M+]＝658.98
Synthesis example 7 Synthesis of Compound 1
< reaction formula 7>
In a round-bottom flask under nitrogen, < intermediate 1-f > (6.0g,9.10mmol), bis (4-tert-butylphenyl) amine (5.63g,20.0mmol), sodium tert-butoxide (4.37g,45.5mmol), bis (tri-tert-butylphosphine) palladium (0) (0.23g,0.46mmol) were added to 80mL of toluene and stirred at reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, and then extracted with toluene and water to remove the water layer. After treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. The resultant was separated and purified by column chromatography, and then recrystallized from toluene and hexane to obtain < compound 1> (6.03g, 60%).
MS[M+]＝1104.5
Synthesis example 8 Synthesis of Compounds 2, 10 and 11
By using<Intermediates 1-f>4-tert-butylphenyl-4-trimethylsilylphenylamine, di-o-tolylamine
2-fluoro-o-tolueneAmine amines
Compounds 2 and 10 and 11 were synthesized according to synthesis example 7, respectively.
A compound 2; MS [ M + ] ═ 1136.6, compound 10; MS [ M + ] ═ 936.1, compound 11; MS [ M + ] -944.1
Synthesis example 9 Synthesis of intermediate 3-a
< intermediate 3-a > was synthesized according to synthesis example 1 using 1-dibenzofuranylboronic acid.
MS[M+]＝356.06
Synthesis example 10 Synthesis of intermediate 3-f
Using < intermediate 3-a >, the < intermediate 3-f > was synthesized according to synthesis examples 2 to 6.
MS[M+]＝658.98
Synthesis example 11 Synthesis of Compounds 3,4, 6 and 7
Synthesis example 12 Synthesis of intermediate 5-a
The < intermediate 5-a > was synthesized according to synthesis example 1 using 1-dimethylfluorenylboronic acid.
MS[M+]＝398.96
Synthesis example 13 Synthesis of intermediate 5-f
Using < intermediate 5-a >, the < intermediate 5-f > was synthesized according to synthesis examples 2 to 6.
MS[M+]＝701.14
Synthesis example 14 Synthesis of Compound 5
Synthesis example 15 Synthesis of intermediate 8-a
< intermediate 8-a > was synthesized according to synthesis example 1 using 4-naphthobenzofuran boronic acid.
MS[M+]＝406.87
Synthesis example 16 Synthesis of intermediate 8-f
Using < intermediate 8-a >, < intermediate 8-f > was synthesized according to synthesis examples 2 to 6.
MS[M+]＝709.04
Synthesis example 17 Synthesis of Compound 8
Compound 8 was synthesized according to Synthesis example 8 using < intermediate 8-f > and bis-4-tert-butylaniline.
Compound 8; MS [ M + ] -1154.5
Synthesis example 18 Synthesis of intermediate 9-a
< intermediate 9-a > was synthesized according to synthesis example 1 using 4-dibenzothiophene boronic acid.
MS[M+]＝372.87
Synthesis example 19 Synthesis of intermediate 9-f
Using < intermediate 9-a >, < intermediate 9-f > was synthesized according to synthesis examples 2 to 6.
MS[M+]＝675.04
Synthesis example 20 Synthesis of Compound 9
Compound 9 was synthesized according to Synthesis example 7 using < intermediate 9-f > and 4-tert-butylphenyl-1-phenylamine.
Compound 9; MS [ M + ] -1008.3
< example >
Example 1.
Will be provided with
Is coated with ITO (indium tin oxide)in oxide) was put in distilled water in which a dispersant was dissolved, and the glass substrate (corning 7059 glass) was washed with ultrasonic waves. At this time, the detergent was prepared by Fischer Co, and distilled water was filtered 2 times by 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, ultrasonic washing was sequentially performed with solvents of isopropyl alcohol, acetone, and methanol, and drying was performed.
On the ITO transparent electrode thus prepared, to
The HAT is thermally vacuum-deposited to a thickness of (1) to form a hole injection layer. Vacuum evaporation is performed on the hole injection layer as a hole transport layer
HT-A as described above, followed by
And evaporating HT-B in thickness. Doping H-A and compound 1 as a host material on the light-emitting layer in an amount of 2-10 wt% to form a mixture
And (5) performing vacuum evaporation on the thickness. Then, in film thickness
ET-A and Liq were deposited at a ratio of 1:1, and successively deposited thereon
Magnesium (Mg) doped with 10 wt% silver (Ag) and
the cathode is formed of aluminum in a thickness to manufacture the organic light emitting element.
In the above process, the evaporation speed of the organic material is maintained
Maintenance of LiF
Deposition rate of (3), aluminum maintenance
To
The deposition rate of (3).
Example 2.
An organic light-emitting element was produced in the same manner as in example 1, except that compound 3 was used instead of compound 1 in example 1.
Example 3.
An organic light-emitting element was produced in the same manner as in example 1, except that compound 4 was used instead of compound 1 in example 1.
Example 4.
An organic light-emitting element was produced in the same manner as in example 1, except that compound 7 was used instead of compound 1 in example 1.
Example 5.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 10 was used instead of the compound 1.
Example 6.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 11 was used instead of the compound 1.
Example 7.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, H — B was used instead of the host material H-a.
Example 8.
An organic light-emitting element was produced in the same manner as in example 7, except that compound 3 was used instead of compound 1 in example 7.
Example 9.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, compound 4 was used instead of compound 1.
Example 10.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, compound 7 was used instead of compound 1.
Example 11.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, compound 10 was used instead of compound 1.
Example 12.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, compound 11 was used instead of compound 1.
Example 13.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 1, the host material H — C was used instead of H-a.
Example 14.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, compound 3 was used instead of compound 1.
Example 15.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, compound 4 was used instead of compound 1.
Example 16.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, compound 7 was used instead of compound 1.
Example 17.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, compound 10 was used instead of compound 1.
Example 18.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, compound 11 was used instead of compound 1.
< comparative example >
Comparative example 1.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, D-1 was used instead of compound 1.
Comparative example 2.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, D-2 was used instead of compound 1.
Comparative example 3.
An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, D-3 was used instead of compound 1.
Comparative example 4.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, D-1 was used instead of compound 1.
Comparative example 5.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, D-2 was used instead of compound 1.
Comparative example 6.
An organic light-emitting element was produced in the same manner as in example 7, except that in example 7, D-3 was used instead of compound 1.
Comparative example 7.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, D-1 was used instead of compound 1.
Comparative example 8.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, D-2 was used instead of compound 1.
Comparative example 9.
An organic light-emitting element was produced in the same manner as in example 13, except that in example 13, D-3 was used instead of compound 1.
The organic light-emitting elements of examples 1 to 18 and comparative examples 1 to 9 described above were measured for driving voltage and light-emitting efficiency at a current density of 10mA/cm and for the time required for the initial luminance to decrease to 95% at a current density of 20mA/cm (LT 95). The results are shown in table 1 below.
[ Table 1]
Comparing examples 1 to 18 of the above table 1 and comparative examples 1 to 9, in the case of an organic light emitting element manufactured including a heterocyclic compound represented by the above chemical formula 1, attenuation of intermolecular fluorescence due to dense intermolecular packing is prevented due to a three-dimensional structure, thereby exhibiting excellent performance. Further, in a state where one electron is lost (cation condition), the electron density distribution of the HOMO is generally distributed in a nitrogen-containing spiroindolocaridine portion known to have a stable cation state, leading to improvement in the lifetime of the device. Therefore, it was confirmed that the efficiency and the life characteristics were excellent as compared with the organic light emitting elements manufactured in comparative examples 1 to 9 including pyrene-based or fluorene-based compounds.
Claims (12)
1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
r5 to R8 are hydrogen,
l1 and L2 are direct bonds,
a and b are each a number of 4,
c is the number of 3,
the value of d is 5, and the value of d is,
n1 and n2 are 1,
x1 and X2 are directly bonded to each other,
ar1-L2-NR3R4 is one of the following structures:
r 'and R' are methyl groups,
r1 to R4, equal to or different from each other, are each independently one of the following structures:
in the structure, in the process of manufacturing the composite material,
r201, R203, R228, R229 and R257 to R259, which are identical or different from one another, are each independently hydrogen, fluorine, trimethylsilyl, methyl or tert-butyl,
a1 is an integer of 0 to 5,
a28, a29 and b18 are integers of 0 to 4,
a3 is an integer from 0 to 7,
when a1, a28, a29, b18 and a3 each represent 2 or more, the substituents in parentheses may be the same or different from each other.
2. The heterocyclic compound according to claim 1, wherein the compound of formula 1 is selected from the following compounds:
3. an organic light-emitting element, comprising: a first electrode, a second 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 claim 1 or 2.
4. The organic light-emitting element according to claim 3, wherein the organic layer comprises a hole injection layer or a hole transport layer,
the hole injection layer or the hole transport layer includes the heterocyclic compound of chemical formula 1.
5. The organic light-emitting element according to claim 3, wherein the organic layer comprises an electron-transporting layer or an electron-injecting layer,
the electron transport layer or the electron injection layer includes the heterocyclic compound of chemical formula 1.
6. The organic light-emitting element according to claim 3, wherein the organic layer comprises a light-emitting layer,
the light emitting layer includes the heterocyclic compound of chemical formula 1.
7. The organic light-emitting element according to claim 6, wherein the light-emitting layer further comprises a compound of the following chemical formula 2:
chemical formula 2
In the chemical formula 2, the first and second organic solvents,
r9 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkyl amine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
p is an integer of 0 to 6,
when p is 2 or more, the substituents in parentheses may be the same or different from each other,
l3 to L6, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
ar2 to Ar5, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
8. The organic light-emitting element according to claim 7, wherein the L3 to L6 are the same as or different from each other, each independently is a direct bond, or is selected from the following structures:
9. the organic light-emitting element according to claim 7, wherein the Ar2 to Ar5 are the same as or different from each other, each independently hydrogen, or are selected from the following structures:
10. the organic light-emitting element according to claim 6, wherein the light-emitting layer further comprises a compound of the following chemical formula 3:
chemical formula 3
In the chemical formula 3, the first and second organic solvents,
r10 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an arylsulfoxide group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylalkyl amine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group,
q is an integer of 0 to 7,
when q is 2 or more, the substituents in parentheses may be the same or different from each other,
l7 to L9, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
ar6 to Ar8, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
11. The organic light-emitting element according to claim 10, wherein the L7 to L9 are the same as or different from each other, each independently is a direct bond, or is selected from the following structures:
12. the organic light-emitting element according to claim 10, wherein the Ar6 to Ar8 are the same as or different from each other, and each is independently selected from the following structures:
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