CN113646915A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN113646915A CN113646915A CN202080026781.5A CN202080026781A CN113646915A CN 113646915 A CN113646915 A CN 113646915A CN 202080026781 A CN202080026781 A CN 202080026781A CN 113646915 A CN113646915 A CN 113646915A
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 494
- 229910052805 deuterium Inorganic materials 0.000 claims description 494
- 239000010410 layer Substances 0.000 claims description 389
- 239000000126 substance Substances 0.000 claims description 293
- 125000003118 aryl group Chemical group 0.000 claims description 234
- 229910052739 hydrogen Inorganic materials 0.000 claims description 214
- 239000001257 hydrogen Substances 0.000 claims description 214
- 125000000217 alkyl group Chemical group 0.000 claims description 207
- 150000002431 hydrogen Chemical group 0.000 claims description 183
- 125000001424 substituent group Chemical group 0.000 claims description 167
- 125000000623 heterocyclic group Chemical group 0.000 claims description 165
- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 145
- 125000005843 halogen group Chemical group 0.000 claims description 141
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 88
- 239000012044 organic layer Substances 0.000 claims description 76
- 238000002347 injection Methods 0.000 claims description 66
- 239000007924 injection Substances 0.000 claims description 66
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000003277 amino group Chemical group 0.000 claims description 61
- 125000004104 aryloxy group Chemical group 0.000 claims description 58
- 125000005110 aryl thio group Chemical group 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000004414 alkyl thio group Chemical group 0.000 claims description 56
- 125000003342 alkenyl group Chemical group 0.000 claims description 54
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- 239000012153 distilled water Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 14
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 14
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- 238000001308 synthesis method Methods 0.000 description 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 11
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 11
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- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
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- 125000004076 pyridyl group Chemical group 0.000 description 10
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- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 9
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- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 4
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Abstract
The present specification provides an organic light emitting device.
Description
Technical Field
The present specification relates to a compound and an organic light emitting device including the same.
The present application claims priority of korean patent application No. 10-2019-0093187 filed by korean patent office at 31.07.2019, the entire contents of which are incorporated herein by reference.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
Disclosure of Invention
Technical subject
In this specification, an organic light-emitting device is described.
Means for solving the problems
An embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, the organic layer including a first organic layer including a compound represented by chemical formula 1 or 2 and a second organic layer including a compound represented by chemical formula 3.
[ chemical formula 1]
In the above-described chemical formula 1,
ar1 to Ar4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
A1, A2, R1 to R3, Z1 and Z2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
n1 to n3 are each an integer of 0 to 3, and when n1 to n3 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
p1 is 0 or 1 and,
[ chemical formula 2]
In the above-described chemical formula 2,
e1 to E3, which are the same or different from each other, are each independently an aromatic hydrocarbon ring,
1 or more of R4 to R8 are represented by the following chemical formula 1-a or 1-B, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
n4 and n5 are each an integer of 0 to 4, n6 is an integer of 0 to 3, n7 and n8 are each an integer of 0 to 5,
n4+ n5+ n6+ n7+ n8 is 1 or more,
when n4 to n8 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
[ chemical formula 1-A ]
[ chemical formula 1-B ]
In the above chemical formulas 1-A and 1-B,
t1 to T17 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
ar11 to Ar14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
L11 is a direct bond or a substituted or unsubstituted arylene group,
p2 is 0 or 1 and,
represents a position to which chemical formula 2 is bound,
[ chemical formula 3]
(HAr)a-L21-Ar21-L22-(CN)b
In the above-mentioned chemical formula 3,
HAr is a substituted or unsubstituted N-containing heterocyclic group,
l21 and L22, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted 2-to 4-valent aryl group, or a substituted or unsubstituted 2-to 4-valent heterocyclic group,
ar21 is a substituted or unsubstituted arylene group, a substituted or unsubstituted 2-valent heterocyclic group, or-O-,
a and b are each an integer of 1 to 3,
when a is 2 or more, the hars may be the same or different from each other.
Effects of the invention
The organic light emitting device described in this specification has a low driving voltage, has excellent efficiency characteristics, and has an excellent lifetime by including the compound represented by chemical formula 1 or 2 in the first organic layer and the compound represented by chemical formula 3 in the second organic layer. Specifically, the electron transport degree is adjusted by appropriately adjusting the HOMO level and the LUMO level, so that a low driving voltage, high efficiency can be achieved, and the lifetime can be improved.
Drawings
Fig. 1, 2, and 8 illustrate examples of an organic light emitting device according to an embodiment of the present specification.
Fig. 3 to 7 illustrate examples of an organic light emitting device including 2 or more stacks.
[ description of symbols ]
1: substrate/2: anode/3: hole injection layer/4: hole transport layer/4 a: first hole transport layer/4 b: second hole transport layer/4 c: third hole transport layer/4 d: fourth hole transport layer/4 e: fifth hole transport layer/4 f: sixth hole transport layer/4 p: p-doped hole transport layer/4R: red hole transport layer/4G: green hole transport layer/4B: blue hole transport layer/5: electron blocking layer/6: light-emitting layer/6 a: first light-emitting layer/6 b: second light-emitting layer/6 c: third light-emitting layer/6 BF: blue fluorescent light-emitting layer/6 BFa: first blue fluorescent light-emitting layer/6 BFb: second blue fluorescent light-emitting layer/6 YGP: yellow-green phosphorescent light-emitting layer/6 RP: red phosphorescent emission layer/6 GP: green phosphorescent light-emitting layer/7: hole blocking layer/8: electron injection and transport layer/9: electron transport layer/9 a: first electron transport layer/9 b: second electron transport layer/9 c: third electron transport layer/10: electron injection layer/11: cathode/12: n-type charge generation layer/12 a: first N-type charge generation layer/12 b: second N-type charge generation layer/13: p-type charge generation layer/13 a: first P-type charge generation layer/13 b: second P-type charge generation layer/14: covering layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides an organic light emitting device including both a first organic layer including a compound represented by chemical formula 1 or 2 and a second organic layer including a compound represented by chemical formula 3. The organic light emitting device has characteristics of low voltage, high efficiency, and long life by simultaneously including the first organic layer and the second organic layer. The light emitting layer including the compound of the above chemical formula 1 or 2 has a shallow HOMO level, and the compound of the above chemical formula 3 has a deep HOMO, LUMO level, and thus electrons can be easily transferred to the light emitting layer, thereby exhibiting high efficiency and lifetime.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
In the context of the present specification, 
Indicates a site to which another substituent or a binding moiety binds.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a cycloalkyl group, an aryl group, an amino group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.
In the present specification, the connection of 2 or more substituents means that the hydrogen of any one substituent is replaced with another substituent. For example, isopropyl is linked to phenyl to form Is composed of
A substituent of (1).
In the present specification, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, 2 phenyl groups and isopropyl groups are linked to form
A substituent of (1). The same explanation as above applies to the case where 4 or more substituents are bonded.
In the present specification, "substituted with a or B" includes not only the case of being substituted with only a or the case of being substituted with only B, but also the case of being substituted with a and B.
In the present specification, "substituted or unsubstituted" means that the substituent is substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an arylthio group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an amino group, and a heterocyclic group having 2 to 30 carbon atoms, or is substituted with a substituent in which 2 or more groups selected from the above group are linked, or does not have any substituent.
In the present specification, "substituted or unsubstituted" means that the substituent is substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an amino group, and a heterocyclic group having 2 to 20 carbon atoms, or is substituted with a substituent in which 2 or more groups selected from the above group are linked, or does not have any substituent.
Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the alkyl group includes a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the above alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and the like, and the above alkyl group may be straight or branched, and according to one example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, isobutyl and tert-butyl.
In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Cycloalkyl groups include not only monocyclic groups but also bicyclic groups such as bridgehead (bridged), fused rings (fused rings), spiro rings (spiro). Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like.
In the present specification, a cycloalkene (cycloalkene) is a cyclic group in which a double bond is present in a hydrocarbon ring but not aromatic, and the number of carbon atoms is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. The cyclic olefins include not only monocyclic groups but also bicyclic groups such as bridgehead, condensed ring, spiro ring and the like. Examples of the cycloolefin include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, and cyclohexene.
In the present specification, alkoxy is a group having an aryl group bonded to an oxygen atom, alkylthio is a group having an alkyl group bonded to a sulfur atom, and the above description of alkyl groups can be applied to the alkyl groups of alkoxy and alkylthio.
In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited but is 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, Biphenyl, terphenyl, quaterphenyl, and the like, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,
Examples of the group include, but are not limited to, a fluorenyl group, a fluoranthenyl group, and a triphenylenyl group.
In the present specification, the carbon atom (C) No. 9 of the fluorenyl group may be substituted with an alkyl group, an aryl group or the like, and 2 substituents may be bonded to each other to form a spiro structure such as cyclopentane, fluorene or the like.
In the present specification, the substituted aryl group may include a form in which an aliphatic ring is fused to the aryl group. For example, the tetrahydronaphthyl group of the structure below is included in the substituted aryl group. In the following structures, one of the carbons of the benzene ring may be attached at other positions.
In this specification, aryloxy is a group having an aryl group bonded to an oxygen atom, arylthio is a group having an aryl group bonded to a sulfur atom, and the above description about aryl groups can be applied to aryl groups of aryloxy and arylthio. The aryl group of the aryloxy group is exemplified by the aryl groups described above. Specifically, the aryloxy group includes, but is not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy, and the like, and the arylthio group includes phenylthio (phenylthio), 2-methylphenylthio, 4-tert-butylphenylthio, and the like.
In the present specification, the silyl group may be represented by-SiYaYbYcThe above-mentioned chemical formula is Ya、YbAnd YcMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstitutedUnsubstituted cycloalkyl, 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 dimethylphenylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In this specification, the boron group may be represented BY-BYdYeThe above-mentioned chemical formula is YdAnd YeMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a dimethylboronyl group, a diethylboronyl group, a tert-butylmethylboronyl group, a vinylmethylboronyl group, a propylmethylboronyl group, a methylphenylboronyl group, a diphenylboronyl group, and a phenylboronyl group.
In the present specification, the amine group may be represented by — NRaRb, and the above Ra and Rb may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, but are not limited thereto. The amine group may be selected from an alkylamino group, an alkylarylamino group, an arylamino group, a heteroarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, depending on the kind of the substituent (Ra, Rb) bonded thereto.
In the present specification, an alkylamino group means an amino group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40, 1 to 20. Specific examples of the alkylamino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, and a diethylamino group.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group. The aryl group in the above arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a bis (tert-butylphenyl) amino group and the like, but the arylamine group 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 arylheteroarylamino group.
In the present specification, arylheteroarylamino means an amino group substituted with an aryl group and a heteroaryl group, and the description about the above aryl group and the below-mentioned heteroaryl group can be applied.
In the present specification, a heterocyclic group is a cyclic group containing at least 1 of N, O, S and Si as a heteroatom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuryl, naphthobenzofuryl, carbazolyl, benzocarbazolyl, naphthobenzothienyl, hexahydrocarbazolyl, dihydroacridinyl, dibenzoazasilyl and thiophene
Examples of the heterocyclic group include, but are not limited to, an oxazinyl group (phenoxazine), a phenothiazinyl group (phenothiazine), a dihydrodibenzoazasilyl group, a spiro (dibenzothiaole-dibenzoazasilyl) group, and a spiro (acridine-fluorene) group.
In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.
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, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent.
In the present specification, "a ring formed by bonding adjacent groups" means a hydrocarbon ring or a heterocyclic ring.
In the present specification, "a five-or six-membered ring formed by combining adjacent groups" means that the ring containing a substituent participating in the ring formation is a five-or six-membered ring. It is possible to include a case where another ring is fused to the above-mentioned ring containing the substituent participating in the ring formation.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a fused ring of an aromatic and an aliphatic, the aromatic hydrocarbon ring may be the aromatic ring except for having a valence of 1, and the aromatic ring may be the aromatic ring except for having a valence of 1, and the aliphatic hydrocarbon ring may be the cycloalkyl ring except for having a valence of 1. Examples of the aromatic and aliphatic condensed ring include, but are not limited to, 1,2,3, 4-tetrahydronaphthyl and 2, 3-dihydro-1H-indenyl.
In the present specification, the description of the heterocyclic group is applicable except that the heterocyclic group is not 1-valent.
In the present specification, the aromatic hydrocarbon ring means a planar ring in which pi electrons are completely conjugated, and the above description on the aryl group can be applied in addition to the 2-valent group.
In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include a cycloalkyl ring. The cycloalkyl ring can be used in addition to the 2-valent group, as described above with respect to the cycloalkyl group. In the substituted aliphatic hydrocarbon ring, an aliphatic hydrocarbon ring fused with an aromatic ring is also included.
In the present specification, the above description about aryl groups can be applied to arylene groups other than those having a valence of 2.
In the present specification, the above description on the cycloalkyl group can be applied to cycloalkylene groups other than the 2-valent group.
Next, chemical formula 1 will be described.
[ chemical formula 1]
In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, Ar1 to Ar4, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms.
In another embodiment, Ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, Ar1 to Ar4, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or a group adjacent to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, wherein the aliphatic hydrocarbon ring may be substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or with 2 or more substituents selected from the group, and wherein a monocyclic to bicyclic aliphatic or aromatic hydrocarbon ring may be fused to the aliphatic hydrocarbon ring.
In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, or combine with an adjacent group to form a six-membered aliphatic hydrocarbon ring, which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, and to which a monocyclic to bicyclic hydrocarbon ring is condensed or not condensed.
In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, or combine with an adjacent group to form a six-membered aliphatic hydrocarbon ring, which is substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, or is unsubstituted, and which is condensed or not condensed with benzene or cyclohexane.
According to another embodiment, Ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted phenyl group, or combine with an adjacent group to form a substituted or unsubstituted cyclohexane, a substituted or unsubstituted tetrahydronaphthalene, or a substituted or unsubstituted decahydronaphthalene. At this time, the adjacent groups may be 2 selected from Ar1 to Ar 4.
According to another embodiment, Ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, a propyl group substituted or unsubstituted with deuterium, a butyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium, or combine with an adjacent group to form a cyclohexane substituted or unsubstituted with deuterium; tetrahydronaphthalene substituted or unsubstituted with deuterium, butyl or phenyl; or decahydronaphthalene substituted or unsubstituted with deuterium. At this time, the adjacent groups may be 2 selected from Ar1 to Ar 4.
According to an embodiment of the present specification, adjacent 2 of Ar1 to Ar4 form a substituted or unsubstituted aliphatic hydrocarbon ring, and the remaining 2 are the above-mentioned substituents.
In the present specification, the meaning that Ar1 to Ar4 bond to each other to form a ring is that Ar1 and Ar3, or Ar2 and Ar4 bond to each other to form a ring.
According to an embodiment of the present specification, when 2 of Ar1 to Ar4 are bonded to each other to form an aliphatic hydrocarbon ring, any one ring selected from the following rings is formed.
In the above ring, Ar101 and Ar102, which are the same as or different from each other, are substituents of Ar1 to Ar4 which do not form an aliphatic hydrocarbon ring,
Y1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
y1 is an integer of 0 to 14, and when Y1 is 2 or more, Y1 are the same as or different from each other.
According to one embodiment of the present specification, Y1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, Y1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group of carbon number 1 to 6, or a substituted or unsubstituted aryl group of carbon number 6 to 20.
According to another embodiment, Y1 is hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, butyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.
According to another embodiment, Y1 is hydrogen, deuterium, methyl, tert-butyl or phenyl.
According to one embodiment of the present description, Y1 is hydrogen, deuterium, or methyl.
In one embodiment of the present specification, y1 is an integer from 0 to 8. In another embodiment, y1 is 0 to 4. In another embodiment, y1 is 0 or 1.
In one embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, Ar101 and Ar102, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, Ar101 and Ar102, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In another embodiment, Ar101 and Ar102 are the same or different from each other, each independently hydrogen, deuterium, fluoro, methyl, ethyl, butyl, or phenyl.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 101 or 102.
In the above-described chemical formulas 101 and 102,
a1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are as defined above in chemical formula 1,
g1 to G4 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
G11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
g11 is an integer of 0 to 8, and when G11 is 2 or more, 2 or more G11 s are the same as or different from each other,
p3 is 0 or 1.
In one embodiment of the present disclosure, the descriptions of Ar1 to Ar4 above may be applied to G1 to G4.
In one embodiment of the present specification, the description of Y1 described above can be applied to G11.
In another embodiment, g11 can be used as described above with respect to y 1.
In one embodiment of the present specification, p3 is 1.
In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to another embodiment, G1 to G4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted phenyl group.
According to another embodiment, G1 to G4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, a propyl group substituted or unsubstituted with deuterium, a butyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
According to one embodiment of the present specification, G11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.
According to another embodiment, G11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
According to another embodiment, G11 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted butyl, or substituted or unsubstituted phenyl, or combines with an adjacent group to form substituted or unsubstituted cyclohexane, or substituted or unsubstituted benzene.
According to another embodiment, G11 is hydrogen, deuterium, methyl, tert-butyl or phenyl, or combines with adjacent groups to form cyclohexane substituted or unsubstituted with methyl, or combines with adjacent groups to form benzene substituted or unsubstituted with butyl or phenyl.
According to one embodiment of the present description, G11 is hydrogen, deuterium, or methyl.
In one embodiment of the present specification, a1 and a2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, a1 and a2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.
In another embodiment, a1 and a2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted ring.
According to another embodiment, a1 and a2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted five-or six-membered ring.
According to another embodiment, A1 and A2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms, or combine with each other to form a five-or six-membered ring,
the aryl group, heterocyclic group or ring of a1 and a2 described above is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a silyl group and an aryl group having 6 to 30 carbon atoms, or with 2 or more substituents selected from the above group, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is fused or unfused.
According to another embodiment, A1 and A2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, or combine with each other to form a five-or six-membered ring,
The aryl group, heterocyclic group or ring of a1 and a2 described above is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group and an aryl group having 6 to 20 carbon atoms, or with 2 or more substituents selected from the above group, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is fused or unfused.
In one embodiment of the present specification, a1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with a2 to form a substituted or unsubstituted ring.
In one embodiment of the present specification, a2 is hydrogen or deuterium, or combines with a1 or R1 to form a substituted or unsubstituted ring.
In another embodiment, a2 is hydrogen or deuterium, or binds with a1 to form a substituted or unsubstituted five or six membered ring, or binds with R1 to form a substituted or unsubstituted five or six membered ring.
In one embodiment of the present description, a2 may combine with an adjacent a1 or R2 to form a ring.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulae 103 to 106.
In the above-described chemical formulae 103 to 106,
r1 to R3, Z1, Z2, p1, Ar1 to Ar4 and n1 to n3 are as defined in the above chemical formula 1,
a3, A4, and G5 through G8 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
z3, Z4, G12 and G13 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
g12 is an integer of 0 to 8, g13 is an integer of 0 to 4, and when g12 and g13 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
p4 and p5 are each 0 or 1.
In one embodiment of the present specification, the above description about a1 can be applied to A3. In another embodiment, the above description of a2 may be applied to a 4.
In one embodiment of the present specification, p4 is the same as p 1.
In one embodiment of the present specification, p5 is 1.
In one embodiment of the present specification, a3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
In another embodiment, a3 is 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, a3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
In another embodiment, the aryl group or heterocyclic group of a3 is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are linked, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is fused or unfused.
In another embodiment, the aryl group or heterocyclic group of a3 is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are linked, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is fused or unfused.
In another embodiment, a3 is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with a condensed or unfused five-or six-membered aliphatic hydrocarbon ring, with 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or with 2 or more substituents selected from the above group bonded together; or a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted by 1 or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 or more carbon atoms which is unsubstituted or substituted by 2 or more groups selected from the above group.
In another embodiment, a3 is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
In another embodiment, a3 is phenyl substituted or unsubstituted with deuterium, fluoro, methyl, ethyl, propyl, butyl, 2-phenylpropan-2-yl (2-phenylpropan-2-yl), Ph-d5, naphthyl, or tetramethyltetrahydronaphthyl; biphenyl substituted or unsubstituted with deuterium, methyl, ethyl, propyl, butyl, trimethylsilyl, 2-phenylpropan-2-yl; terphenyl optionally substituted with deuterium or butyl; naphthyl substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted by deuterium, methyl or phenyl; fluorenyl substituted or unsubstituted with deuterium or methyl; dibenzofuranyl substituted or unsubstituted with deuterium or butyl; or dibenzothienyl substituted or unsubstituted with deuterium or butyl.
In one embodiment of the present specification, a4 is hydrogen or deuterium, or combines with R1 to form a substituted or unsubstituted ring.
In another embodiment, a2 is hydrogen or deuterium, or combines with R1 to form a substituted or unsubstituted five or six membered ring.
In another embodiment, a2 is hydrogen or deuterium, or combines with R1 to form a five or six membered ring substituted or unsubstituted with deuterium or an alkyl group of 1 to 6 carbon atoms.
In another embodiment, the five or six membered ring formed by combining a2 with R1 is benzofuran, benzothiophene, or indene.
In one embodiment of the present disclosure, the descriptions of G5 to G8 may be applied to the descriptions of G1 to G4. In another embodiment, G12 and G13 may be adapted as described above with respect to G11.
In one embodiment of the present specification, G5 to G8 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to another embodiment, G5 to G8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted phenyl group.
According to another embodiment, G5 to G8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, a propyl group substituted or unsubstituted with deuterium, a butyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, G12 and G13 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.
According to another embodiment, G12 and G13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or combine with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
According to another embodiment, G12 and G13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted trimethylsilyl group, or a substituted or unsubstituted phenyl group, or combine with adjacent groups to form a substituted or unsubstituted cyclohexane, or a substituted or unsubstituted benzene.
According to another embodiment, G12 combines with an adjacent G12 to form a substituted or unsubstituted ring.
According to another embodiment, G13 combines with an adjacent G13 to form a substituted or unsubstituted ring.
According to another embodiment, G12 is hydrogen, deuterium or methyl, or combines with each other with the adjacent G12 to form cyclohexane.
In another embodiment, G13 is hydrogen, deuterium, methyl, trimethylsilyl, or phenyl, or combines with the adjacent G13 to form a benzene substituted or unsubstituted with phenyl.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
In the above chemical formulas 1-1 to 1-4,
r1 to R3, n1 to n3 and Ar1 to Ar4 are as defined in the above chemical formula 1,
a3 and A4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
Z1 to Z4 and Ar21 to Ar24 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring.
In the present specification, the meaning that adjacent groups of Ar21 to Ar24 are bonded to each other to form a ring is i) 2 groups of Ar21 to Ar24 are bonded to each other to form an aliphatic hydrocarbon ring, or ii) all of Ar21 to Ar24 participate in ring formation to form an aromatic hydrocarbon ring.
In one embodiment of the present specification, the above description of the substituents G5 to G8, the aliphatic hydrocarbon ring to which G11 is bonded, and the aromatic hydrocarbon ring to which G12 is bonded can be applied to Ar21 to Ar 24.
In one embodiment of the present specification, Ar21 to Ar24, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring.
In another embodiment, Ar21 to Ar24, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, Ar21 to Ar24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or combine with an adjacent group to form a six-membered hydrocarbon ring which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms and to which a monocyclic to bicyclic hydrocarbon ring is fused or not fused.
In another embodiment, Ar21 to Ar24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or combine with an adjacent group to form a six-membered hydrocarbon ring substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms, which is condensed or not condensed with cyclohexane or benzene.
According to another embodiment, Ar21 to Ar24, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group, or combine with adjacent groups to form a substituted or unsubstituted cyclohexane, a substituted or unsubstituted benzene, or a substituted or unsubstituted decalin. At this time, the adjacent groups may be 2 selected from Ar21 to Ar 24.
According to another embodiment, Ar21 to Ar24, equal to or different from each other, are each independently hydrogen, deuterium, a halogen group, cyano, methyl, ethyl or phenyl, or combine with adjacent groups to form cyclohexane; decahydronaphthalene; benzene substituted or unsubstituted with methyl, tert-butyl or trimethylsilyl; or naphthalene substituted or unsubstituted with phenyl. At this time, the adjacent groups may be 2 selected from Ar21 to Ar 24.
According to an embodiment of the present specification, when 2 of Ar21 to Ar24 are bonded to each other to form a hydrocarbon ring, any one ring selected from the following rings is formed.
In the above ring, Ar103 and Ar104, which are the same as or different from each other, are substituents of Ar21 to Ar24 which do not form an aliphatic hydrocarbon ring,
Y2 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
y2 is an integer of 0 to 14, and when Y2 is 2 or more, Y2 are the same as or different from each other.
In one embodiment of the present specification, y2 is an integer from 0 to 8. In another embodiment, y2 is 0 to 4. In another embodiment, y2 is 0 or 1.
In one embodiment of the present specification, Ar103 and Ar104, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, Ar103 and Ar104, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, Ar103 and Ar104, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In another embodiment, Ar103 and Ar104 are the same or different from each other, each independently hydrogen, deuterium, fluoro, methyl, ethyl, butyl, or phenyl.
According to one embodiment of the present specification, Y2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, Y2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group of carbon number 1 to 6, a substituted or unsubstituted alkylsilyl group of carbon number 1 to 18, a substituted or unsubstituted arylsilyl group of carbon number 6 to 60, or a substituted or unsubstituted aryl group of carbon number 6 to 20.
According to another embodiment, Y2 is hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, butyl substituted or unsubstituted with deuterium, trimethylsilyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.
According to another embodiment, Y2 is hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted trimethylsilyl group, or a substituted or unsubstituted phenyl group.
According to one embodiment of the present description, Y2 is hydrogen, deuterium, or methyl.
According to an embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, R1 to R3, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of carbon atoms 1 to 30, a substituted or unsubstituted arylsilyl group of carbon atoms 6 to 90, a substituted or unsubstituted alkyl group of carbon atoms 1 to 10, a substituted or unsubstituted aryl group of carbon atoms 6 to 30, a substituted or unsubstituted arylamine group of carbon atoms 6 to 60, a substituted or unsubstituted heteroarylamine group of carbon atoms 2 to 90, or a substituted or unsubstituted heterocyclic group of carbon atoms 2 to 30, or combine with an adjacent group to form a substituted or unsubstituted ring of carbon atoms 2 to 30.
In another embodiment, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.
In another embodiment, R1 to R3, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of carbon atoms 1 to 18, a substituted or unsubstituted arylsilyl group of carbon atoms 6 to 60, a substituted or unsubstituted alkyl group of carbon atoms 1 to 6, a substituted or unsubstituted aryl group of carbon atoms 6 to 20, NY11Y12, or a substituted or unsubstituted heterocyclic group of carbon atoms 2 to 20, or combine with an adjacent group to form a substituted or unsubstituted ring of carbon atoms 2 to 20.
In another embodiment, R1 to R3, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; NY11Y 12; or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or with 2 or more substituents selected from the above group, or a ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or with 2 or more substituents selected from the above group, bonded to adjacent groups.
In another embodiment, R1 to R3, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; NY11Y 12; or a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or with 2 or more substituents selected from the above group, or a ring having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or with 2 or more substituents selected from the above group, bonded to adjacent groups.
In another embodiment, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, NY11Y12, a substituted or unsubstituted N-containing heterocyclic group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or combine with an adjacent group to form a substituted or unsubstituted benzofuran, a substituted or unsubstituted ring.
In another embodiment, R1 to R3, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted biphenylamino group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenyldibenzothiophenyl group, a substituted or unsubstituted N-containing heterocyclic group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or combine with an adjacent group to form a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclohexene.
In another embodiment, R1 to R3 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted biphenylamino group, a substituted or unsubstituted phenyldibenzofuran amino group, a substituted or unsubstituted phenyldibenzothiophene amino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted hexahydrocarbazolyl group, a substituted or unsubstituted dihydroacridinyl group, a substituted or unsubstituted thiophene.
An oxazinyl group (phenoxazine), a substituted or unsubstituted phenothiazinyl group (phenothiazine), a substituted or unsubstituted dihydrodibenzoazasilyl group, a substituted or unsubstituted spiro (dibenzothiaole-dibenzoazasilyl), a substituted or unsubstituted spiro (acridine-fluorene), a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or combine with an adjacent group to form a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclohexene.
According to another embodiment, R1 to R3, equal to or different from each other, are each independently hydrogen; deuterium; a fluorine group; methyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with deuterium; tert-butyl substituted or unsubstituted with deuterium; trimethylsilyl substituted or unsubstituted with deuterium; by deuterium, fluoro, methyl, trifluoromethyl, trimethylsilylAlkyl or naphthyl substituted or unsubstituted phenyl; naphthyl substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD3T-butyl, 2-phenylpropan-2-yl, trimethylsilyl, triphenylsilyl or a diphenylamino group substituted or unsubstituted with phenyl and fused with or without hexene; a substituted or unsubstituted phenylnaphthylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a biphenylylamino group substituted or unsubstituted with deuterium or tert-butyl; a phenyldibenzofuran amine group substituted or unsubstituted with deuterium, methyl or tert-butyl, and condensed or unfused with hexene; phenyl dibenzothiophene amine groups substituted or unsubstituted with deuterium, methyl or tert-butyl, and fused or unfused with hexene; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; hexahydrocarbazolyl, fused or unfused with hexane, hexene or benzene, substituted or unsubstituted with deuterium, fluoro, cyano, methyl, phenyl or Ph-d 5; dihydroacridinyl substituted or unsubstituted by methyl, ethyl or phenyl; phen 
An oxazine group; a phenothiazinyl group; a dihydrodibenzoazasilyl group substituted or unsubstituted with a phenyl group; spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzothiaole-dibenzoazasilyl) group; a dibenzofuranyl group; or dibenzothienyl.
According to another embodiment, R1 to R3 combine with adjacent groups to form benzofuran substituted or unsubstituted with tert-butyl or phenyl, naphthobenzofuran, thiophene substituted or unsubstituted with tert-butyl, indole substituted or unsubstituted with phenyl, indene substituted or unsubstituted with methyl or tert-butyl, spiro (fluorene-indene) substituted or unsubstituted with tert-butyl, cyclopentene substituted or unsubstituted with methyl, or cyclohexene substituted or unsubstituted with methyl.
According to another embodiment, adjacent 2R 1, R1 and a2, R1 and a4, or adjacent 2R 2 combine with adjacent groups to form benzofuran substituted or unsubstituted with tert-butyl or phenyl, naphthobenzofuran, thiophene substituted or unsubstituted with tert-butyl, indole substituted or unsubstituted with phenyl, indene substituted or unsubstituted with methyl or tert-butyl, spiro (fluorene-indene) substituted or unsubstituted with tert-butyl, cyclopentene substituted or unsubstituted with methyl, or cyclohexene substituted or unsubstituted with methyl.
In another embodiment, the N-containing heterocyclic group of R1 to R3 described above may be represented by any one of the following chemical formulae HAr1 to HAr3 or chemical formula 1-B.
In the above chemical formulae HAr1 to HAr3,
q1 is CY4Y5 or SiY4Y5, Q2 is C or Si,
y3 to Y5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic ring,
when Y3 is an integer of 0 to 8 and Y3 is 2 or more, 2 or more Y3 s are the same as or different from each other.
According to an embodiment of the present specification, Y3 to Y5 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, Y3 to Y5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to another embodiment, Y3 to Y5, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, butyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.
According to another embodiment, Y3 to Y5, equal to or different from each other, are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl or phenyl.
According to another embodiment, Y3 is methyl.
According to another embodiment, Y4 and Y5, equal to or different from each other, are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl or phenyl.
In one embodiment of the present specification, Y11 and Y12, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted fused ring group having 9 to 30 carbon atoms of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a substituted or unsubstituted fused ring group having 9 to 20 carbon atoms of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12, which are the same as or different from each other, are each independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent formed by connecting 2 or more groups selected from the above group; or a condensed ring group having 9 to 30 carbon atoms which is a C9-30 condensed ring group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring, the condensed ring group being substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent formed by connecting 2 or more substituents selected from the above group.
In another embodiment, Y11 and Y12, which are the same as or different from each other, are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; a heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent formed by connecting 2 or more groups selected from the above group; or a condensed ring group having 9 to 20 carbon atoms which is a C9-20 condensed ring group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring, the condensed ring group being substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent formed by connecting 2 or more substituents selected from the above group.
In another embodiment, Y11 and Y12, which are the same as or different from each other, are each independently an aryl group of carbon number 6 to 30 substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group of carbon number 1 to 10, an arylalkyl group of carbon number 7 to 60, an alkylsilyl group of carbon number 1 to 30, or an arylsilyl group of carbon number 6 to 90; a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; or a condensed ring group of 9 to 30 carbon atoms which is an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted or unsubstituted with deuterium or an alkyl group of 1 to 10 carbon atoms.
In another embodiment, Y11 and Y12, which are the same as or different from each other, are each independently an aryl group of carbon number 6 to 20 substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group of carbon number 1 to 6, an arylalkyl group of carbon number 7 to 40, an alkylsilyl group of carbon number 1 to 18, or an arylsilyl group of carbon number 6 to 60; a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms; or a condensed ring group of 9 to 20 carbon atoms which is an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted or unsubstituted with deuterium or an alkyl group of 1 to 6 carbon atoms.
In another embodiment, Y11 and Y12, which are the same or different from each other, are each independently a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted tetrahydronaphthyl.
In another embodiment, Y11 and Y12, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms; naphthyl substituted or unsubstituted with deuterium, a halogen group, cyano, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms; dibenzothienyl substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms; or tetrahydronaphthyl substituted or unsubstituted by deuterium or an alkyl group having 1 to 6 carbon atoms.
In another embodiment, Y11 and Y12, equal to or different from each other, are each independently deuterium, fluoro, cyano, methyl, CD3Phenyl substituted or unsubstituted with butyl, trimethylsilyl, triphenylsilyl, or 2-phenylpropan-2-yl; biphenyl substituted or unsubstituted with deuterium; naphthyl substituted or unsubstituted with deuterium; dibenzofuranyl substituted or unsubstituted with deuterium or butyl; dibenzothienyl substituted or unsubstituted with deuterium or butyl; or tetrahydronaphthyl substituted or unsubstituted by deuterium or methyl.
In one embodiment of the present specification, R1 to R3 combine with adjacent groups to form a ring represented by Cy11 or Cy12 described below. Specifically, adjacent 2R 1, R1 and a2, R1 and a4, or adjacent 2R 2 are bonded to each other to form a ring represented by the following chemical formula Cy11 or Cy 12.
[ chemical formula Cy11] [ chemical formula Cy12]
In the above chemical formulas Cy11 and Cy12,
the double dashed line is the position of the fusion,
q3 is O, S, NY9, CY10Y11 or SiY10Y11,
y7 to Y11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic ring, or combine with an adjacent group to form a substituted or unsubstituted ring,
p10 is 1 or 2,
y6 is an integer of 0 to 4, y8 is an integer of 0 to 8, and when y6 and y8 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other.
According to an embodiment of the present specification, Y7 to Y11 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a ring having 3 to 30 carbon atoms.
According to another embodiment, Y7 to Y11, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or combine with an adjacent group to form a ring having 3 to 20 carbon atoms.
According to another embodiment, Y7 to Y11, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, butyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium, or combine with adjacent groups to form hexane substituted or unsubstituted with deuterium, hexene substituted or unsubstituted with deuterium, or benzene substituted or unsubstituted with deuterium.
According to another embodiment, Y7 to Y11, equal to or different from each other, are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl or phenyl.
According to another embodiment, Y7 is hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, or butyl substituted or unsubstituted with deuterium, or combines with each other with adjacent Y7 to form benzene substituted or unsubstituted with deuterium, or hexene substituted or unsubstituted with deuterium.
According to another embodiment, Y8 is hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, or butyl substituted or unsubstituted with deuterium, or combines with each other with adjacent Y7 to form benzene substituted or unsubstituted with deuterium, or hexane substituted or unsubstituted with deuterium.
According to another embodiment, Y9 is phenyl substituted or unsubstituted with deuterium.
In another embodiment, in the above formulas Cy11 and Cy12, Y10 and Y11 are the same as or different from each other, each independently is a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium or butyl, or Y10 and Y11 are each a phenyl group substituted or unsubstituted with deuterium or butyl, and combine with each other to form fluorene substituted or unsubstituted with deuterium or butyl.
In another embodiment, in the above formulas Cy11 and Cy12, Y10 and Y11 are the same as or different from each other, each independently is a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium or a butyl group, or Y10 and Y11 are each a phenyl group substituted or unsubstituted with deuterium or a butyl group, and combine with each other to form dibenzosilole (dibenzosilole) substituted or unsubstituted with deuterium or a butyl group.
In one embodiment of the present specification, y6 is 0 or 1.
In one embodiment of the present specification, y8 is 2 or more. In another embodiment, y8 is 4.
In one embodiment of the present specification, Y8 is 2 or more, and 2 of Y8 are substituted or unsubstituted alkyl groups. In another embodiment, Y8 is 2 or more and 2 of Y8 are methyl substituted or unsubstituted with deuterium.
In one embodiment of the present specification, adjacent 2R 1, R1 and a2, R1 and a4, or adjacent 2R 2 are bonded to each other to form a ring represented by the above chemical formula Cy 11.
In another embodiment, adjacent 2R 1 or adjacent 2R 2 are bound to each other to form a ring represented by the above formula Cy 12.
In one embodiment of the present specification, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; a fluorine group; methyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with deuterium; tert-butyl substituted or unsubstituted with deuterium; trimethylsilyl substituted or unsubstituted with deuterium; phenyl unsubstituted or substituted by deuterium, fluoro, methyl, trifluoromethyl, trimethylsilyl or naphthyl; naphthyl substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD 3T-butyl, 2-phenylpropan-2-yl, trimethylsilyl, triphenylsilyl or a diphenylamino group substituted or unsubstituted with phenyl and fused with or without hexene; a substituted or unsubstituted phenylnaphthylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a biphenylylamino group substituted or unsubstituted with deuterium or tert-butyl; a phenyldibenzofuran amine group substituted or unsubstituted with deuterium, methyl or tert-butyl, and condensed or unfused with hexene; phenyl dibenzothiophene amine groups substituted or unsubstituted with deuterium, methyl or tert-butyl, and fused or unfused with hexene; hexahydrocarbazolyl substituted or unsubstituted by deuterium, fluoro, cyano, methyl, phenyl or Ph-d5, condensed or unfused with hexane, hexene or benzene, or combined with an adjacent group to form benzofuran, naphthobenzofuran, thiophene substituted or unsubstituted by tert-butyl or phenyl, benzofuran, naphthobenzofuran, thiophene substituted or unsubstituted by tert-butyl, benzene or a mixture thereofAn indole substituted or unsubstituted by a methyl or tert-butyl group, a spiro (fluorene-indene) substituted or unsubstituted by a tert-butyl group, a cyclopentene substituted or unsubstituted by a methyl group, or a cyclohexene substituted or unsubstituted by a methyl group.
In one embodiment of the present description, R3 is hydrogen; deuterium; a fluorine group; methyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with deuterium; tert-butyl substituted or unsubstituted with deuterium; phenyl unsubstituted or substituted by deuterium, fluoro, methyl, trifluoromethyl, trimethylsilyl or naphthyl; naphthyl substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD3T-butyl, 2-phenylpropan-2-yl, trimethylsilyl, triphenylsilyl or a diphenylamino group substituted or unsubstituted with phenyl and fused with or without hexene; a substituted or unsubstituted phenylnaphthylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a biphenylylamino group substituted or unsubstituted with deuterium or tert-butyl; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; hexahydrocarbazolyl, fused or unfused with hexane, hexene or benzene, substituted or unsubstituted with deuterium, fluoro, cyano, methyl, phenyl or Ph-d 5; dihydroacridinyl substituted or unsubstituted by methyl, ethyl or phenyl; phen
An oxazine group; a phenothiazinyl group; a dihydrodibenzoazasilyl group substituted or unsubstituted with a phenyl group; spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzothiaole-dibenzoazasilyl) group; a dibenzofuranyl group; or a dibenzothienyl group.
According to an embodiment of the present description, n1 and n2 are integers from 0 to 2.
According to another embodiment, n1 and n2 are 0 or 1.
According to an embodiment of the present description, n3 is 0 or 1.
According to an embodiment of the present description, p1 is 0 or 1.
In one embodiment of the present specification, Z1 to Z4, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, Z1 through Z4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, Z1 through Z4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In another embodiment, Z1 through Z4, equal to or different from each other, are each independently hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is represented by any one of the following compounds.
Next, chemical formula 2 will be described.
[ chemical formula 2]
According to one embodiment of the present specification, E1 to E3 are the same as or different from each other, and each is independently an aromatic hydrocarbon ring.
According to another embodiment, E1 to E3, equal to or different from each other, are each independently benzene or naphthalene.
According to another embodiment, E1 and E2, equal to or different from each other, are each independently benzene or naphthalene.
According to another embodiment, E3 is benzene.
According to another embodiment, E1 to E3 are benzene.
In one embodiment of the present specification, 1 or more of R4 to R8 are represented by the following chemical formula 1-a or 1-B, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, the others are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring.
[ chemical formula 1-A ]
[ chemical formula 1-B ]
In the above chemical formulas 1-A and 1-B,
t1 to T17 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
ar11 to Ar14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
L11 is a direct bond or a substituted or unsubstituted arylene group,
p2 is 0 or 1 and,
represents the binding site of chemical formula 2.
In the present specification, the heterocyclic group includes the above chemical formula 1-B.
According to another embodiment, 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, and the others are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms is bonded to an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.
According to another embodiment, 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring.
According to another embodiment, 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dimethylamino group, or a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted dihydroacridine group.
In one embodiment of the present specification, i) 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or ii) adjacent 2R 4 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or iii) adjacent 2R 5 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or iv) adjacent 2R 6 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or v) adjacent 2R 7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or vi) adjacent 2R 8 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, i) 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or ii) adjacent 2R 4 are combined with each other to form a five-or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or iii) adjacent 2R 5 are combined with each other to form a five-or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or iv) adjacent 2R 6 are combined with each other to form a five-or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or v) adjacent 2R 7 are combined with each other to form a five-or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or vi) adjacent 2R 8 are combined with each other to form a five-or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group. In this case, the aliphatic hydrocarbon ring of ii) to vi) may contain 1 or more alkyl groups as substituents, and may contain substituents other than alkyl groups.
In another embodiment, i) 1 or more of R4 to R8 are represented by the above chemical formula 1-A or 1-B, or ii) adjacent 2R 4 combine with each other to form pentene substituted or unsubstituted by methyl, or hexene substituted or unsubstituted by methyl, or iii) adjacent 2R 5 combine with each other to form pentene substituted or unsubstituted by methyl, or hexene substituted or unsubstituted by methyl, or iv) adjacent 2R 6 combine with each other to form pentene substituted or unsubstituted by methyl, or hexene substituted or unsubstituted by methyl, or v) adjacent 2R 7 combine with each other to form pentene substituted or unsubstituted by methyl, or hexene substituted or unsubstituted by methyl, or vi) adjacent 2R 8 combine with each other to form pentene substituted or unsubstituted by methyl, or hexene substituted or unsubstituted by methyl. In this case, the above methyl group may be substituted by deuterium.
The compound of the above chemical formula 2 may correspond not only to one of the above i) to vi) but also to 2 or more of i) to vi). That is, the compound 2 may correspond to the i) and the ii).
In one embodiment of the present specification, 1 or more of R4 to R8, which are the same as or different from each other as the remaining substituents (hereinafter referred to as "the remaining substituents in R4 to R8") that are not bound to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, are represented by the above chemical formula 1-a or 1-B, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring.
In another embodiment, the remaining substituents in R4 to R8 may be applicable to the description of R1 to R3 described above with respect to chemical formula 1.
In another embodiment, the remaining substituents in R4 to R8, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of carbon atoms of 1 to 30, a substituted or unsubstituted arylsilyl group of carbon atoms of 6 to 90, a substituted or unsubstituted alkyl group of carbon atoms of 1 to 10, a substituted or unsubstituted aryl group of carbon atoms of 6 to 30, a substituted or unsubstituted alkylamino group of carbon atoms of 1 to 30, a substituted or unsubstituted arylamine group of carbon atoms of 6 to 60, a substituted or unsubstituted heteroarylamino group of carbon atoms of 2 to 90, or a substituted or unsubstituted heterocyclic group of carbon atoms of 2 to 30, or combine with an adjacent group to form a substituted or unsubstituted ring of carbon atoms of 2 to 30.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of carbon atoms of 1 to 18, a substituted or unsubstituted arylsilyl group of carbon atoms of 6 to 60, a substituted or unsubstituted alkyl group of carbon atoms of 1 to 6, a substituted or unsubstituted aryl group of carbon atoms of 6 to 20, a substituted or unsubstituted alkylamino group of carbon atoms of 1 to 18, a substituted or unsubstituted arylamine group of carbon atoms of 6 to 60, a substituted or unsubstituted heteroarylamino group of carbon atoms of 2 to 60, or a substituted or unsubstituted heterocyclic group of carbon atoms of 2 to 20, or combine with an adjacent group to form a substituted or unsubstituted ring of carbon atoms of 2 to 20.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of carbon atoms of 1 to 18, a substituted or unsubstituted arylsilyl group of carbon atoms of 6 to 60, a substituted or unsubstituted alkyl group of carbon atoms of 1 to 6, a substituted or unsubstituted aryl group of carbon atoms of 6 to 20, a substituted or unsubstituted alkylamino group of carbon atoms of 1 to 18, NY11Y12, or a substituted or unsubstituted heterocyclic group of carbon atoms of 2 to 20, or combine with an adjacent group to form a substituted or unsubstituted ring of carbon atoms of 2 to 20.
In another embodiment, the remaining substituents in R4 to R8, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; an alkylamino group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; NY11Y 12; or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or with 2 or more substituents selected from the above group, or a ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or with 2 or more substituents selected from the above group, bonded to adjacent groups.
In another embodiment, the remaining substituents in R4 to R8, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; a substituted or unsubstituted alkylamino group having 1 to 18 carbon atoms; NY11Y 12; or a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or with 2 or more substituents selected from the above group, or a ring having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or with 2 or more substituents selected from the above group, bonded to adjacent groups.
In another embodiment, the remaining substituents in R4 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dimethylamino group, NY11Y12, a substituted or unsubstituted N-containing heterocyclic group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or combine with an adjacent group to form a substituted or unsubstituted benzofuran, a substituted or unsubstituted ring.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylamino group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted biphenylamino group, a substituted or unsubstituted phenyldibenzofuran amino group, a substituted or unsubstituted phenyldibenzothiophene amino group, a substituted or unsubstituted N-containing heterocyclic group, a substituted or unsubstituted heterocyclic group, a heterocyclic group, and a method for producing a compound, Substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination of adjacent groups to form substituted or unsubstituted benzofuran, substituted or unsubstituted thiophene, substituted or unsubstituted indole, substituted or unsubstituted indene, substituted or unsubstituted cyclopentene, or substituted or unsubstituted cyclohexene.
In another embodiment, the remaining substituents in R4 to R8, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylamino group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dihydroacridinyl group, a substituted or unsubstituted thiophene group
An oxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted dihydrodibenzoazasilyl group, a substituted or unsubstituted spiro (dibenzothiaole-dibenzoazasilyl), a substituted or unsubstituted spiro (acridine-fluorene), a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or combine with an adjacent group to form a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclohexene.
According to another embodiment, the remaining substituents in R4 to R8, equal to or different from each other, are each independently hydrogen; deuterium; a fluorine group; methyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with deuterium; tert-butyl substituted or unsubstituted with deuterium; trimethylsilyl substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, trifluoromethyl, trimethylsilyl, butyldimethylsilylPhenyl substituted or unsubstituted with silyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluoro or tert-butyl; terphenyl optionally substituted with deuterium; naphthyl substituted or unsubstituted with deuterium; fluorenyl substituted or unsubstituted with deuterium, methyl; dimethylamino substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD3T-butyl, 2-phenylpropan-2-yl, trimethylsilyl, triphenylsilyl or a diphenylamino group substituted or unsubstituted with phenyl and fused with or without hexene; a substituted or unsubstituted phenylnaphthylamino group substituted or unsubstituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamino group substituted or unsubstituted with deuterium or a tert-butyl group; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; dihydroacridinyl substituted or unsubstituted by methyl, ethyl or phenyl; phen 
An oxazine group; a phenothiazinyl group; a dihydrodibenzoazasilyl group substituted or unsubstituted with a phenyl group; spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzothiaole-dibenzoazasilyl) group; a dibenzofuranyl group; or dibenzothienyl.
According to another embodiment, the remaining substituents of R4 to R8 combine with adjacent groups to form benzofuran substituted or unsubstituted with tert-butyl or phenyl, naphthobenzofuran, thiophene substituted or unsubstituted with tert-butyl, indole substituted or unsubstituted with phenyl, indene substituted or unsubstituted with methyl or tert-butyl, spiro (fluorene-indene) substituted or unsubstituted with tert-butyl, cyclopentene substituted or unsubstituted with methyl, or cyclohexene substituted or unsubstituted with methyl.
According to another embodiment, adjacent 2R 4, adjacent 2R 5, adjacent 2R 6, adjacent 2R 7, or adjacent 2R 8 combine with each other to form benzofuran, naphthobenzofuran, thiophene, indole, indene, spiro (fluorene-indene), cyclopentene, or cyclohexene substituted or unsubstituted with methyl.
In another embodiment, the N-containing heterocyclic group of R4 through R8 may be represented by any one of the above formulas HAr1 through HAr3, or the above formula 1-B.
In one embodiment of the present specification, the remaining substituents of R4 to R8 combine with adjacent groups to form a ring represented by Cy11 or Cy12 described above. Specifically, adjacent 2R 4, adjacent 2R 5, adjacent 2R 6, adjacent 2R 7, or adjacent 2R 8 are bonded to each other to form a ring represented by the following chemical formula Cy11 or Cy 12.
In one embodiment of the present specification, adjacent 2R 7 or adjacent 2R 8 are bonded to each other to form a ring represented by the following chemical formula Cy 11.
In another embodiment, adjacent 2R 4, adjacent 2R 5, adjacent 2R 6, adjacent 2R 7, or adjacent 2R 8 are bonded to each other to form a ring represented by the following chemical formula Cy 12.
In one embodiment of the present specification, the chemical formula 2 is represented by any one of chemical formulas 201 to 203.
[ chemical formula 203]
In the above-described chemical formulas 201 to 203,
e1 to E3, n4 to n8 are as defined in chemical formula 2,
r4 to R8, R11 and R12, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
p6 and p7 are each 1 or 2,
n5 'is an integer of 0 to 2, n 8' is an integer of 0 to 3, n11 and n12 are each an integer of 0 to 8,
when n5 ', n 8', n11 and n12 are each 2 or more, the substituents in parentheses of 2 or more are the same as or different from each other.
In one embodiment of the present specification, R11 and R12, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 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, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, R11 and R12, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, R11 and R12, which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, R11 and R12, which are the same as or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or combine with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms which is substituted or unsubstituted with deuterium.
In another embodiment, R11 and R12, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium, or combine with an adjacent group to form a benzene ring substituted or unsubstituted with deuterium or butyl, or combine with an adjacent group to form an indene ring substituted or unsubstituted with deuterium, methyl or butyl, or combine with an adjacent group to form a spiro (fluorene-indene) substituted or unsubstituted with deuterium, methyl or butyl.
In another embodiment, R11 and R12, equal to or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.
In one embodiment of the present specification, n4 to n6 are each 0 or 1.
In one embodiment of the present specification, the chemical formula 2 is represented by any one of the following chemical formulae 211 to 219.
[ chemical formula 219]
In the above-described chemical formulas 211 to 219,
n4 to n8 are as defined in chemical formula 2,
r4 to R8 and R11 to R14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
p6 to p9 are each 1 or 2,
n4 'and n 5' are each an integer of 0 to 2, n7 'and n 8' are each an integer of 0 to 3, n11 to n14 are each an integer of 0 to 8,
when n4 ', n 5', n7 ', n 8' and n11 to n14 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other.
In one embodiment of the present specification, R4 to R8 of the above chemical formulae 211 to 219 are hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, the above description of R11 can be applied to R13. In another embodiment, the above description of R12 can be applied to R14.
In another embodiment, R13 and R14, which are the same as or different from each other, are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or combine with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted or unsubstituted with deuterium.
In another embodiment, R13 and R14, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium, or combine with an adjacent group to form a benzene ring substituted or unsubstituted with deuterium or butyl, or combine with an adjacent group to form an indene ring substituted or unsubstituted with deuterium, methyl or butyl, or combine with an adjacent group to form a spiro (fluorene-indene) substituted or unsubstituted with deuterium, methyl or butyl.
In one embodiment of the present specification, 1 or more of R4 to R8 are bonded to an adjacent group to form an aliphatic hydrocarbon ring,
1 or more of the aliphatic hydrocarbon rings are represented by any one of the following chemical formulas Cy1 to Cy 3.
In the above chemical formulae Cy1 to Cy3,
r31 to R40, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group,
r41 to R43 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
n41 is an integer of 0 to 2, n42 and n43 are each an integer of 0 to 4,
when n41 to n43 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other.
In the present specification, the aliphatic hydrocarbon ring included in chemical formula 2 means one or more rings of 1) an aliphatic hydrocarbon ring in which 2R 4 are bonded to each other, 2) an aliphatic hydrocarbon ring in which 2R 5 are bonded to each other, 3) an aliphatic hydrocarbon ring in which 2R 6 are bonded to each other, 4) an aliphatic hydrocarbon ring in which 2R 7 are bonded to each other, and 5) an aliphatic hydrocarbon ring in which 2R 8 are bonded to each other.
In one embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
In another embodiment, R31 to R40, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
In another embodiment, R31 to R40 are substituted or unsubstituted methyl.
In another embodiment, R41 to R43, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, R41 to R43, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.
In another embodiment, R41 and R42, equal to or different from each other, are each independently hydrogen or deuterium.
In another embodiment, R43 is hydrogen or deuterium, or adjacent 4R 43 combine with each other to form a substituted or unsubstituted benzene ring.
In another embodiment, R43 is hydrogen or deuterium, or adjacent 4R 43 are bonded to each other to form a benzene ring substituted or unsubstituted with 1 or more substituents selected from deuterium and an alkyl group having 1 to 6 carbon atoms, or with 2 or more substituents bonded to each other.
In another embodiment, R43 is hydrogen or deuterium, or adjacent 4R 43 combine with each other to form a benzene ring.
In another embodiment, all the aliphatic hydrocarbon rings contained in the above chemical formula 2 are selected from the above structures,
in another embodiment, 1 or more of the aliphatic hydrocarbon rings included in the above chemical formula 2 are selected from the following structures.
In another embodiment, 1 to 4 of the aliphatic hydrocarbon rings contained in the above chemical formula 2 are selected from the above structures.
In another embodiment, one or more rings selected from the group consisting of 1) an aliphatic hydrocarbon ring in which 2R 4 are bonded to each other, 2) an aliphatic hydrocarbon ring in which 2R 5 are bonded to each other, 3) an aliphatic hydrocarbon ring in which 2R 6 are bonded to each other, 4) an aliphatic hydrocarbon ring in which 2R 7 are bonded to each other, and 5) an aliphatic hydrocarbon ring in which 2R 8 are bonded to each other are selected from the above structures.
In one embodiment of the present specification, chemical formula 2 is represented by chemical formula 204 below.
[ chemical formula 204]
In the chemical formula 204 described above,
1 or more of R21 to R25 are represented by chemical formula 1-a or 1-B, and the others are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to each other to form a substituted or unsubstituted ring,
E1 to E3, n4 to n8, chemical formula 1-A and 1-B are as defined in the above chemical formula 2.
In one embodiment of the present specification, T1 to T11 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
According to another embodiment, T1 to T11, which are the same or different from each other, are each independently hydrogen or deuterium, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
According to another embodiment, T1 to T11, which are the same or different from each other, are each independently hydrogen or deuterium, or combine with adjacent groups to form a substituted or unsubstituted bridgehead or fused aliphatic hydrocarbon ring.
According to another embodiment, T1 to T11, which are the same as or different from each other, are each independently hydrogen or deuterium, or T1, T4 and T8 are bonded to each other to form a substituted or unsubstituted bridgehead or fused ring aliphatic hydrocarbon ring, or T2, T6 and T10 are bonded to each other to form a substituted or unsubstituted bridgehead or fused ring aliphatic hydrocarbon ring.
In one embodiment of the present specification, L11 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In another embodiment, L11 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
In another embodiment, L11 is a 6 to 20 carbon atom arylene group bonded directly to or substituted with an alkyl group having 1 to 6 carbon atoms.
In another embodiment, L11 is a direct bond, or a substituted or unsubstituted phenylene group.
In another embodiment, L11 is phenylene directly bonded, or substituted or unsubstituted with deuterium or tert-butyl.
In one embodiment of the present specification, the chemical formula 1-a is represented by the following chemical formula 1-a-1 or 1-a-2.
In one embodiment of the present specification, the chemical formula 1-B is represented by the following chemical formula 1-B-1 or 1-B-2.
In another embodiment, the above chemical formula 1-A is represented by the following chemical formula 1-A-1 or 1-A-2, and the above chemical formula B-1 is represented by the following chemical formula 1-B-1 or 1-B-2.
[ chemical formula 1-A-1]
[ chemical formula 1-A-2]
[ chemical formula 1-B-1]
[ chemical formula 1-B-2]
In the above chemical formulas 1-A-1 and 1-A-2, L11 is as defined in the above chemical formula 1-A,
in the above chemical formulas 1-B-1 and 1-B-2, T12 to T17 and p2 are defined as same as those in the above chemical formula 1-B,
t18 to T21 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
t22 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to each other to form a substituted or unsubstituted ring,
When T22 is an integer of 0 to 8 and T22 is 2 or more, 2 or more T22 s are the same as or different from each other.
In one embodiment of the present specification, the cyclohexyl and adamantyl groups of the above chemical formulas 1-A-1 and 1-A-2 may be substituted or unsubstituted.
In one embodiment of the present specification, the cyclohexyl and adamantyl groups of the above chemical formulas 1-A-1 and 1-A-2 may be substituted with deuterium or an alkyl group having 1 to 6 carbon atoms or unsubstituted.
In one embodiment of the present specification, T12 to T17 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, T12 to T17, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, T12 to T17, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.
In another embodiment, T12 to T17, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or a ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or with 2 or more substituents selected from the group connected, bonded to adjacent groups.
In another embodiment, T12 to T17, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkylarylsilyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; an arylalkyl group of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; or a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or a ring having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or with 2 or more substituents selected from the group connected, bonded to adjacent groups.
In another embodiment, T12 to T15, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted methylsilyl group, a substituted or unsubstituted butylsilyl group, a substituted or unsubstituted phenylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridyl group, or combine with an adjacent group to form a substituted or unsubstituted hexene, or a substituted or unsubstituted benzene.
In another embodiment, T12 to T15, equal to or different from each other, are each independently hydrogen; deuterium; a halogen group; a cyano group; methyl substituted or unsubstituted with deuterium; ethyl substituted or unsubstituted with deuterium; propyl substituted or unsubstituted with deuterium; butyl substituted or unsubstituted with deuterium; trimethylsilyl substituted or unsubstituted with deuterium; butyldimethylsilyl substituted or unsubstituted with deuterium; dimethylphenylsilyl substituted or unsubstituted with deuterium; methyldiphenylsilyl substituted or unsubstituted with deuterium; triphenylsilyl substituted or unsubstituted with deuterium; phenyl substituted or unsubstituted with deuterium, cyano, methyl or butyl; biphenyl substituted or unsubstituted with deuterium, cyano, methyl or butyl; naphthyl substituted or unsubstituted with deuterium; or pyridyl substituted or unsubstituted by deuterium, or combine with an adjacent group to form hexene substituted or unsubstituted by deuterium or methyl, or benzene substituted or unsubstituted by deuterium or methyl.
In another embodiment, T16 and T17, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted methyl group.
In one embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, Ar11 to Ar14, which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent 2 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, Ar11 to Ar14, which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent 2 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
In another embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently represents hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or adjacent 2 groups are bonded to each other to form an aliphatic hydrocarbon ring having 3 to 20 carbon atoms which is substituted or unsubstituted with deuterium and to which an aromatic hydrocarbon ring having 6 to 20 carbon atoms is fused or not fused.
In another embodiment, Ar11 to Ar14, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, phenyl substituted or unsubstituted with deuterium, or pyridyl, or adjacent 2 groups are bound to each other to form cyclohexane or tetrahydronaphthalene.
In one embodiment of the present specification, 2 of Ar11 to Ar14, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the remaining 2 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, 2 of Ar11 to Ar14, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, phenyl substituted or unsubstituted with deuterium, or pyridyl, and the remaining 2 are combined with each other to form cyclohexane or tetrahydronaphthalene.
In one embodiment of the present disclosure, the descriptions of Ar11 to Ar14 above apply to T18 to T21.
In another embodiment, T18 through T21, which are the same as or different from each other, are each independently hydrogen, deuterium, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium, an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or a heterocyclic group of 2 to 20 carbon atoms substituted or unsubstituted with deuterium.
In another embodiment, T18 to T21, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, phenyl substituted or unsubstituted with deuterium, or pyridyl.
In one embodiment of the present specification, the above description of Ar11 to Ar14 applies to T22.
In another embodiment, T22 is hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or adjacent 2 groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.
In another embodiment, T22 is hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium, or adjacent 2 groups are joined to each other to form a benzene substituted or unsubstituted with deuterium.
In one embodiment of the present specification, t22 is an integer of 0 to 4. In another embodiment, t22 is an integer from 0 to 2.
In one embodiment of the present specification, 1 or more of R4 to R8 are represented by the above chemical formula 1-a. In another embodiment, 2 or more of R4 to R8 are represented by the above chemical formula 1-a.
In one embodiment of the present specification, R4 is represented by chemical formula 1-a above.
In one embodiment of the present specification, R5 is represented by chemical formula 1-a above.
In one embodiment of the present specification, R6 is represented by chemical formula 1-a above.
In one embodiment of the present specification, R7 is represented by chemical formula 1-a above.
In one embodiment of the present specification, R8 is represented by chemical formula 1-a above.
In one embodiment of the present specification, 1 or more of R4 to R8 are represented by the above chemical formula 1-B. In another embodiment, 2 or more of R4 to R8 are represented by the above chemical formula 1-B.
In one embodiment of the present specification, R4 is represented by chemical formula 1-B above.
In one embodiment of the present specification, R5 is represented by chemical formula 1-B above.
In one embodiment of the present specification, R6 is represented by chemical formula 1-B above.
In one embodiment of the present specification, R7 is represented by chemical formula 1-B above.
In one embodiment of the present specification, R8 is represented by chemical formula 1-B above.
In one embodiment of the present specification, n4 and n5 are each an integer of 0 to 4. In another embodiment, n4 and n5 are each integers from 0 to 2.
In one embodiment of the present specification, n6 is an integer of 0 to 3. In another embodiment, n6 is 0 or 1.
In one embodiment of the present specification, n7 and n8 are each an integer of 0 to 5. In another embodiment, n7 and n8 are each integers from 0 to 3. n7 and n8 are each 0 or 1.
According to an embodiment of the present specification, the compound represented by the above chemical formula 2 is represented by any one of the following compounds.
Next, chemical formula 3 will be described.
[ chemical formula 3]
(HAr)a-L21-Ar21-L22-(CN)b
In one embodiment of the present specification, HAr is a substituted or unsubstituted N-containing monocyclic to 3-ring heterocyclic group.
In one embodiment of the present specification, HAr is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzimidazolyl group.
In one embodiment of the present specification, HAr is represented by any one of the following chemical formulae a1 to a 5.
[ chemical formula A1]
[ chemical formula A2]
[ chemical formula A3]
[ chemical formula A4]
[ chemical formula A5]
In the above chemical formulas a1 to a5,
x1 to X3, equal to or different from each other, are each independently N, CH or CD,
at least one of X1 to X3 is N,
ar22 and Ar23, 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, or combine with each other with adjacent groups to form a substituted or unsubstituted ring,
r21 to R26, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
n21 is an integer of 0 to 7, n22 is an integer of 0 to 5, n24 and 26 are integers of 0 to 4, and when n21, n22, n24 and n26 are each 2 or more, substituents in parentheses of 2 or more are the same as or different from each other.
The dotted line indicates a site connected to L21.
In one embodiment of the present specification, the chemical formula a1 is any one selected from the following chemical formulae.
In the above chemical formulae, the dotted lines, Ar22, and Ar23 are the same as defined in chemical formula a 1.
In one embodiment of the present specification, the chemical formula a2 is any one selected from the following chemical formulae.
In the above chemical formula, the dotted line, R21, and n21 are the same as defined in chemical formula a 2.
In one embodiment of the present specification, the chemical formula a3 is any one selected from the following chemical formulae.
In the above chemical formula, the dotted line, R22, and n22 are the same as defined in chemical formula A3.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic 2 to 4-valent aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic 2 to 4-valent heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic 2 to 4-valent aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic 2 to 4-valent heterocyclic group having 2 to 20 carbon atoms.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond; or one selected from the group consisting of a substituted or unsubstituted 2 to 4 valent phenyl group, a substituted or unsubstituted 2 to 4 valent biphenyl group, a substituted or unsubstituted 2 to 4 valent terphenyl group, a substituted or unsubstituted 2 to 4 valent tetrabiphenyl group, and a substituted or unsubstituted 2 to 4 valent naphthyl group; or a 2-valent group in which 2 or more groups selected from the above groups are linked.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond; or one selected from the group consisting of a substituted or unsubstituted 2 to 4 valent phenyl group, a substituted or unsubstituted 2 to 4 valent biphenyl group, a substituted or unsubstituted 2 to 4 valent terphenyl group, a substituted or unsubstituted 2 to 4 valent tetrabiphenyl group, and a substituted or unsubstituted 2 to 4 valent naphthyl group; or 2-valent groups formed by connecting 2 groups selected from the group.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted 2-to 4-valent phenyl group, a substituted or unsubstituted 2-to 4-valent biphenyl group, a substituted or unsubstituted 2-to 4-valent terphenyl group, a substituted or unsubstituted 2-to 4-valent tetrabiphenyl group, or a substituted or unsubstituted 2-to 4-valent naphthyl group.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond; or a monocyclic or polycyclic, 2-to 4-valent aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are linked.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond; or a monocyclic or polycyclic, 2-to 4-valent aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a cyano group, an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms, or a substituent in which 2 or more groups selected from the above group are linked.
In one embodiment of the present specification, L21 and L22, which are the same or different from each other, are each independently a direct bond; a 2-to 4-valent phenyl group substituted or unsubstituted with deuterium, cyano, phenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl or pyridyl; a biphenyl group of 2 to 4 valences substituted or unsubstituted with deuterium, cyano or pyridyl; a 2-to 4-valent terphenyl group substituted or unsubstituted with deuterium or a cyano group; a 2 to 4 valent biphenylyl group substituted or unsubstituted with deuterium or cyano; or 2-to 4-valent naphthyl substituted or unsubstituted by deuterium or cyano.
In one embodiment of the present specification, a is 1 or 2.
In one embodiment of the present specification, b is 1 or 2.
In one embodiment of the present specification, the chemical formula 3 is represented by the following chemical formula 3-1 or 2-2.
[ chemical formula 3-1]
HAr1-L24-Ar21-L22-(CN)b
[ chemical formula 3-2]
In the above chemical formulas 3-1 and 2-2,
l22 and b are the same as defined in chemical formula 3 above,
HAr1 to HAr3 are as defined above for HAr,
l24 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
l25 is a substituted or unsubstituted 3-valent aryl group, or a substituted or unsubstituted 3-valent heterocyclic group.
In one embodiment of the present specification, the above description of L21 applies to L24 and L25.
In one embodiment of the present specification, — L22- (CN) of the above chemical formula 3bSelected from the following structures.
In the above-described structure, the first and second electrodes,
l23 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
r51 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n51 is an integer of 0 to 4, n51' is an integer of 0 to 3,
the dotted line is the position to which Ar21 is attached.
In one embodiment of the present specification, L23 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present specification, L23 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
In one embodiment of the present specification, L23 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L23 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, R51 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R51 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R51 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
In one embodiment of the present description, R51 is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of a cyano group, an aryl group having 2 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded.
In one embodiment of the present description, R51 is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of a cyano group, an aryl group having 2 to 20 carbon atoms and a heterocyclic group having 2 to 25 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded.
In one embodiment of the present description, R51 is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with a cyano group, an aryl group having 2 to 25 carbon atoms or a heterocyclic group having 2 to 25 carbon atoms.
In one embodiment of the present description, R51 is hydrogen; deuterium; phenyl unsubstituted or substituted by cyano or pyridyl; fluorenyl substituted or unsubstituted with phenyl; phenanthryl; a dibenzofuranyl group; a dibenzothienyl group; spiro [ fluorene-xanthene ] yl; or spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, Ar21 is a direct bond, a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic 2-valent heterocyclic group having 2 to 30 carbon atoms, or — O-.
In one embodiment of the present specification, Ar21 is a direct bond, a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic 2-valent heterocyclic group having 2 to 25 carbon atoms, or — O-.
In one embodiment of the present specification, Ar21 is a direct bond, a substituted or unsubstituted monocyclic arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted polycyclic arylene group having 10 to 25 carbon atoms, a substituted or unsubstituted polycyclic 2-valent heterocyclic group having 12 to 25 carbon atoms, or — O-.
In one embodiment of the present specification, Ar21 is 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 binaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted dibenzofuranyl group having a valence of 2, a substituted or unsubstituted dibenzothiophenyl group having a valence of 2, a substituted or unsubstituted spiro [ fluorene-xanthene ] group having a valence of 2, a substituted or unsubstituted spiro [ fluorene-thioxanthene ] group having a valence of 2, or-O-.
In one embodiment of the present description, Ar21 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms, or a substituent in which 2 or more groups selected from the above group are bonded; a monocyclic or polycyclic 2-valent heterocyclic group having 2 to 30 carbon atoms; or-O-.
In one embodiment of the present description, Ar21 is a direct bond; a monocyclic arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 25 carbon atoms or a heterocyclic group having 2 to 25 carbon atoms; a polycyclic arylene group having 10 to 25 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; a polycyclic 2-valent heterocyclic group having 12 to 25 carbon atoms; or-O-.
In one embodiment of the present specification, Ar21 is a phenylene group which is unsubstituted or substituted with a diphenylfluorenyl group, a spiro [ fluorene-xanthene ] group or a spiro [ fluorene-thioxanthene ] group; biphenylene substituted or unsubstituted with diphenylfluorenyl, spiro [ fluorene-xanthene ] yl or spiro [ fluorene-thioxanthene ] yl; a terphenylene group substituted or unsubstituted with a diphenylfluorenyl group, a spiro [ fluorene-xanthene ] group or a spiro [ fluorene-thioxanthene ] group; a naphthylene group; a binaphthylene group; a fluorenylene group substituted or unsubstituted with a methyl group or a phenyl group; spirobifluorene group; a 2-valent dibenzofuranyl group; a 2-valent dibenzothienyl group; a spiro [ fluorene-xanthene ] group having a valence of 2; a spiro [ fluorene-thioxanthene ] group having a valency of 2; or-O-.
In one embodiment of the present specification, Ar21 is a direct bond, phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, or spirobifluorenylene.
In one embodiment of the present specification, Ar21 is-O-, or is selected from the following structures.
In the above-described structure, the first and second electrodes,
x4 and X5, which are identical to or different from each other, are each independently CR52R53, O or S,
r27 to R30, R52 and R53, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n27, n28, n28', n29 and n30 are each integers of 0 to 4,
n29 'and n30' are each an integer of 0 to 3,
n29 'and n30' are each an integer of 0 to 2,
n28+ n28' is 6 or less,
when n27, n28 to n30 and n28 'to n30' are each 2 or more, the substituents in parentheses 2 or more are the same as or different from each other,
when n29 'and n30' are each 2, the substituents in parentheses are the same as or different from each other,
the dotted line is a position connected to the above L21 or L22.
In one embodiment of the present specification, X4 is O or S.
In one embodiment of the present specification, X5 is CR52R 53.
In one embodiment of the present specification, X5 is O or S.
In one embodiment of the present specification, R52 and R53, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R52 and R53, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R52 and R53, which are the same or different from each other, are each independently a methyl group substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R27 to R30, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R27 to R30 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R27 to R30 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.
In one embodiment of the present specification, R27 to R30, which are the same or different from each other, are each independently hydrogen, deuterium, a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group, a spirobifluorenyl group substituted or unsubstituted, a spiro [ fluorene-xanthene ] group substituted or unsubstituted, or a spiro [ fluorene-thioxanthene ] group substituted or unsubstituted.
In one embodiment of the present specification, R27 is hydrogen, deuterium, a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted spiro [ fluorene-xanthene ] group, or a substituted or unsubstituted spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, R28 to R30, which are the same or different from each other, are each independently hydrogen or deuterium.
In one embodiment of the present specification, the phenylene group (2-valent phenyl group) of L21, L22, L24, or Ar21 is one selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. Specifically, the substituent group bonded to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the biphenylene group (biphenyl group having a valence of 2) of L21, L22, L24 or Ar21 is one selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Specifically, the substituent group bonded to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the terphenylene group (2-valent terphenyl group) of L21, L22, L24, or Ar21 is one selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. Specifically, the substituent group bonded to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the naphthylene group (2-valent naphthyl group) of L21, L22, L24 or Ar21 is one selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. Specifically, the substituent group bonded to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the binaphthylene group (the 2-valent binaphthyl group) of L21, L22, L24, or Ar21 is one selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. Specifically, the substituent group bonded to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, at least 2 or more of X1 to X3 are N.
In one embodiment of the present specification, X1 to X3 are each N.
In one embodiment of the present specification, Ar22 and Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, Ar22 and Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 25 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 25 carbon atoms.
In one embodiment of the present specification, Ar22 and Ar23, which are the same as or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted spiro [ fluorene-xanthene ] group, or a substituted or unsubstituted spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, Ar22 and Ar23 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a spiro [ fluorene-xanthene ] group, or a spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, R21 to R26 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R21 to R26, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R21 to R26, 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 tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, R21 to R26, which are the same or different from each other, are each independently hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, a tert-butyl group substituted or unsubstituted with deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, or a naphthyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R21 to R26, which are the same or different from each other, are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl, phenyl, biphenyl, or naphthyl.
In one embodiment of the present specification, R22 is hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, R23 is hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, R25 is hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
In one embodiment of the present specification, R21, R24, and R26 are the same or different from each other, and each is independently hydrogen or deuterium.
In one embodiment of the present description, R21, R24, and R26 are each hydrogen.
In one embodiment of the present specification, the compound represented by the above chemical formula 3 is any one selected from the following compounds.
According to an embodiment of the present invention, the compounds of chemical formulas 1 and 2 may be produced as shown in the following reaction formula 1, and the compound of chemical formula 3 may be produced as shown in the following reaction formula 2. The following reaction formulae 1 and 2 describe the synthesis of some compounds corresponding to chemical formulae 1 to 3 of the present application, but various compounds corresponding to chemical formulae 1 to 3 of the present application can be synthesized by the synthesis procedures shown in the following reaction formulae 1 and 2, substituents can be bonded by a method known in the art, and the kind, position and number of substituents can be changed according to the techniques known in the art.
[ reaction formula 1]
[ reaction formula 2]
In the above reaction scheme 1, A1To A3Represents an aromatic hydrocarbon ring, and R represents a substituent attached to the nucleus, and may be R1 to R8, A1 or A2 of the present invention. In the above reaction formula 2, the substituents are as defined above.
The organic light emitting device of the present specification can be manufactured by using a general method and material for manufacturing an organic light emitting device, in addition to forming the first organic layer using the compound represented by chemical formula 1 or 2 and forming the second organic layer using the compound represented by chemical formula 3.
The first organic layer including the compound represented by chemical formula 1 or 2 and the second organic layer including the compound represented by chemical formula 3 may be formed by a solution coating method as well as a vacuum evaporation method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device in this specification may be formed of a structure including only the first organic layer and the second organic layer, or may be formed of a structure further including another organic layer. The other organic layer may be 1 or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.
In the organic light-emitting device according to one embodiment of the present specification, the first electrode is an anode, the second electrode is a cathode, the first organic layer is a light-emitting layer, and the second organic layer is provided between the second electrode and the first organic layer. That is, the second organic layer is provided between the cathode and the light-emitting layer.
In an organic light-emitting device according to an embodiment of the present specification, the first organic layer is a light-emitting layer.
In the organic light emitting device according to one embodiment of the present specification, the first organic layer is a light emitting layer, and the compound represented by the chemical formula 1 or 2 is included as a dopant of the light emitting layer.
In the organic light emitting device according to one embodiment of the present specification, the first organic layer is a light emitting layer, and the compound represented by the chemical formula 1 or 2 is used as a dopant of the light emitting layer and further includes a fluorescent host or a phosphorescent host. At this time, the dopant in the light emitting layer may be included by 1 to 50 parts by weight, preferably 0.1 to 30 parts by weight, and more preferably 1 to 10 parts by weight, with respect to 100 parts by weight of the host. When within the above range, energy transfer from the host to the dopant occurs efficiently.
In one embodiment of the present specification, the host is an anthracene derivative.
In one embodiment of the present disclosure, the organic layer includes 2 or more light emitting layers, and 1 of the 2 or more light emitting layers includes the compound represented by chemical formula 1 or 2.
In one embodiment of the present specification, the maximum emission peaks of the 2 or more light-emitting layers are different from each other. The light emitting layer including the compound represented by the above chemical formula 1 or 2 is blue, and the light emitting layer not including the compound represented by the above chemical formula 1 or 2 may include a blue, red or green light emitting compound known in the art.
In one embodiment of the present specification, a light-emitting layer including a compound represented by chemical formula 1 or 2 includes a fluorescent dopant, and a light-emitting layer not including a compound represented by chemical formula 1 or 2 includes a phosphorescent dopant.
In one embodiment of the present specification, the maximum emission peak of the light-emitting layer including the compound represented by the above chemical formula 1 or 2 is 400nm to 500 nm. That is, the light emitting layer including the compound represented by the above chemical formula 1 or 2 emits blue light.
The organic layer of the organic light emitting device according to an embodiment of the present specification includes 2 or more light emitting layers, the maximum light emission peak of one light emitting layer (light emitting layer 1) is 400nm to 500nm, and the maximum light emission peak of the other light emitting layer (light emitting layer 2) may show a maximum light emission peak of 510nm to 580nm, or 610nm680 nm. At this time, the light emitting layer 1 includes the compound represented by the above chemical formula 1 or 2.
In an organic light emitting device according to an embodiment of the present specification, the second organic layer is an electron transporting region. Specifically, the second organic layer includes 1 or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
In an organic light emitting device according to another embodiment, the second organic layer includes 1 or 2 layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
In an organic light emitting device according to another embodiment, the second organic layer is a hole blocking layer, an electron transporting layer, an electron injecting layer, or an electron injecting and transporting layer.
In an organic light emitting device according to another embodiment, the second organic layer is a hole blocking layer.
In an organic light emitting device according to another embodiment, the second organic layer is an electron transport layer.
In an organic light emitting device according to another embodiment, the second organic layer is an electron injection and transport layer.
In an organic light emitting device according to another embodiment, the second organic layer includes a hole blocking layer, and an electron injection and transport layer.
In one embodiment of the present specification, the second organic layer is provided in contact with the first organic layer.
In one embodiment of the present specification, the second organic layer further contains 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.
When the organic alkali metal compound or the organic alkaline earth metal compound is used as the n-type dopant, stability of holes in the light emitting layer can be secured, so that the life of the organic light emitting device can be improved. In addition, the electron mobility of the electron transport layer, the proportion of the organic alkali metal compound or the organic alkaline earth metal compound may be adjusted to maximize the balance of holes and electrons in the light emitting layer, thereby increasing the light emitting efficiency.
In this specification, LiQ is more preferable as the n-type dopant used for the second organic layer.
The second organic layer may include the compound of chemical formula 2 and the n-type dopant at a weight ratio of 1:9 to 9: 1. Preferably, the compound of the above chemical formula 2 and the above n-type dopant may be contained at 2:8 to 8:2, and more preferably, may be contained at 3:7 to 7: 3.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is an anode.
In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure in which an anode, 1 or more organic layers, and a cathode (normal type) are sequentially stacked on a substrate.
In one embodiment of the present disclosure, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1, 2, and 8, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 3 may be contained in the hole blocking layer 7 or the electron injection and transport layer 8.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 3 may be contained in the electron injecting and transporting layer 8.
Fig. 8 illustrates a substrate 1 stacked in this order; an anode 2; a p-doped hole transport layer 4 p; hole transport layers 4R, 4G, 4B; light-emitting layers 6RP, 6GP, 6 BF; a first electron transport layer 9 a; a second electron transport layer 9 b; an electron injection layer 10; cathode 11 and capping layer 14. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the light emitting layer 6RP, 6GP, 6BF, and the compound represented by the above chemical formula 3 may be contained in 1 or more layers among the first electron transporting layer 9a, the second electron transporting layer 9b and the electron injecting layer 10.
According to an embodiment of the present disclosure, the organic light emitting device may have a series structure in which two or more independent devices are connected in series. In one embodiment, the series structure may be a form in which the respective organic light emitting devices are bonded by a charge generation layer. The device having the series structure can be driven at a lower current than the unit device with the same luminance as a reference, and therefore, the device has an advantage that the lifetime characteristics are greatly improved.
According to an embodiment of the present disclosure, the organic layer includes: a first stacked body including 1 or more light emitting layers; a second stacked body including 1 or more light emitting layers; and a charge generation layer having 1 or more layers between the first stacked body and the second stacked body.
According to an embodiment of the present disclosure, the organic layer includes: a first stacked body including 1 or more light emitting layers; a second stacked body including 1 or more light emitting layers; and a third stacked body including 1 or more light emitting layers, each of which includes 1 or more charge generation layers between the first stacked body and the second stacked body and between the second stacked body and the third stacked body.
In the present specification, a Charge Generating layer (Charge Generating layer) refers to a layer that generates holes and electrons when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In this specification, the N-type charge generation layer refers to a charge generation layer provided closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer provided closer to the cathode than the N-type charge generation layer.
The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and an NP junction is formed. Holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer by the NP junction. Electrons are transported in the anode direction by the LUMO level of the N-type charge generation layer, and holes are transported in the cathode direction by the HOMO level of the P-type organic layer.
The above-described first stack, second stack, and third stack each include 1 or more light-emitting layers, and may further include 1 or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer which performs both hole transport and hole injection (a hole injection and transport layer), and a layer which performs both electron transport and electron injection (an electron injection and transport layer).
An organic light emitting device including the above-described first stack body and second stack body is illustrated in fig. 3.
Fig. 3 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, an N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second light emitting layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the first light emitting layer 6a or the second light emitting layer 6b, and the compound represented by the above chemical formula 3 may be contained in the first electron transporting layer 9a or the electron injecting and transporting layer 8.
Organic light emitting devices including the above-described first to third stacks are illustrated in fig. 4 to 7.
Fig. 4 illustrates an example of the structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light-emitting layer 6a, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a second hole transport layer 4b, a second light-emitting layer 6b, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a third hole transport layer 4c, a third light-emitting layer 6c, a third electron transport layer 9c, and a cathode 11 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the first, second, and third light emitting layers 6a, 6b, and 6c, and the compound represented by the above chemical formula 3 may be contained in 1 or more layers among the first, second, and third electron transport layers 9a, 9b, and 9 c.
Fig. 5 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light emitting layer 6RP, a yellow green phosphorescent light emitting layer 6YGP, a green phosphorescent light emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 3 may be contained in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.
Fig. 6 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light emitting layer 6RP, a green phosphorescent light emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a cover layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 3 may be contained in 1 or more layers among the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.
Fig. 7 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a first P-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a fourth hole transport layer 4d, a second blue fluorescent light emitting layer 6BFb, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fifth hole transport layer 4e, a sixth hole transport layer 4f, a third blue fluorescent light emitting layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 or 2 may be contained in 1 or more layers among the first blue fluorescent light-emitting layer 6BFa, the second blue fluorescent light-emitting layer 6BFb, and the third blue fluorescent light-emitting layer 6BFb, and the compound represented by the above chemical formula 2 may be contained in 1 or more layers among the first electron transporting layer 9a, the second electron transporting layer 9c, the third electron transporting layer 9c, and the electron injecting layer 10.
The N-type charge generation layer may be 2,3,5, 6-tetrafluoro-7, 7,8, 8-tetracyanodimethyl-p-benzoquinone (F4TCNQ), fluorine-substituted 3,4,9, 10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylamine derivatives, or the like, but is not limited thereto. In one embodiment, the N-type charge generation layer may include both a benzimidazolephenanthrene derivative and Li metal.
The P-type charge generation layer may contain both an arylamine derivative and a cyano group-containing compound.
The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that the organic layer contains the above-described compound.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances. The organic light emitting device according to the present specification may be manufactured as follows: the organic el device is manufactured by forming an anode by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate, forming an organic layer including the first organic layer and the second organic layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
The organic layer including the above-described first organic layer and second organic layer may be a multilayer structure further including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, and the like. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method using various polymer materials.
The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as Zinc Oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer that serves to smoothly inject holes from the anode into the light-emitting layer, and has a single-layer or multilayer structure of 2 or more layers. The hole injecting substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. In one embodiment of the present specification, the hole injection layer has a 2-layer structure, and each layer contains the same or different substances.
The hole transport layer may have a single-layer structure or a multilayer structure having 2 or more layers, and serves to smoothly transport holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously. In one embodiment of the present specification, the hole transport layer has a 2-layer structure, and each layer contains the same or different substances.
The above-mentioned hole injection and transport layer is a layer that simultaneously performs hole transport and hole injection, and a hole transport layer material and/or a hole injection layer material known in the art may be used.
The above-mentioned electron injection and transport layer is a layer that simultaneously performs electron transport and electron injection, and an electron transport layer material and/or an electron injection layer material known in the art may be used.
An electron blocking layer may be provided between the hole transport layer and the light-emitting layer. The electron blocking layer may be made of a material known in the art.
The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an 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; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent material such as piqir (acac) (bis (1-phenylisoquinoline) acetylacetonatoiridium, bis (1-phenylisoquinoline) acetylacetonatoiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonatoiridium, bis (1-phenylquinoline) acetylacetonatoiridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), PtOEP (octylporphyrin, platinum octaethylporphyrin), or Alq (r) may be used 3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits green light, Ir (ppy) can be used as a light-emitting dopant3Phosphorescent substances such as fac tris (2-phenylpyridine) iridium, and Alq tris (2-phenylpyridine) iridium3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits blue light, (4, 6-F) may be used as the light-emitting dopant2ppy)2Examples of the fluorescent substance include phosphorescent substances such as Irpic and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers, but the fluorescent substances are not limited thereto.
The electron transport layer and the light-emitting layer may be provided with a hole-blocking layer therebetween, and materials known in the art may be used.
The electron transport layer functions to smooth the transport of electrons. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq 3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto.
The electron injection layer serves to smoothly inject electrons. As the electron-injecting substance, the following compounds are preferred: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect for a light-emitting layer or a light-emitting material, and having an excellent thin film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
Hereinafter, in order to specifically explain the present specification, the details will be explained by referring to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.
The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that 1 or more of the organic layers are formed using the heterocyclic compound.
Synthesis example 1 Synthesis of Compound 1
1) Synthesis of intermediate 1
40g of 1-bromo-3-chloro-5-methylbenzene, 54.8g of bis (4- (tert-butyl) phenyl) amine, 56.1g of sodium tert-butoxide, and 1.0g of bis (tri-tert-butylphosphino) palladium (0) were added to 600ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 2 hours. After completion of the reaction, extraction was performed, and then, 65g of intermediate 1 was obtained by recrystallization. (yield 82%). MS [ M + H ] ]+＝407
2) Synthesis of intermediate 2
Under nitrogen atmosphere, 30g of intermediate 1, 30.5g of N- (5- (tert-butyl) - [1,1' -biphenyl]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, 14.2g of sodium tert-butoxide, 0.4g of bis (tri-tert-butylphosphine) palladium (0) were added to 450ml of toluene, followed by stirring at reflux for 2 hours. After completion of the reaction, extraction was performed, and then, 45g of intermediate 2 was obtained by recrystallization. (yield 78%). MS [ M + H ]]+＝782
3) Synthesis of Compound 1
25g of intermediate 2 and 21.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 8g of compound 1 (yield 32%). MS [ M + H ]]+＝789
Synthesis example 2 Synthesis of Compound 2
1) Synthesis of intermediate 3
For 30g of intermediate 1 and 38.6g of N- (4- (tert-butyl) -2- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) phenyl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 46g of intermediate 3 was obtained by recrystallization using the same materials and equivalents as those used for the synthesis of intermediate 2. (yield 70%). MS [ M + H ]]+＝892
2) Synthesis of Compound 2
25g of intermediate 3 and 20.2g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 8.1g of compound 2 (yield 31%). MS [ M + H ] ]+＝900
Synthesis example 3 Synthesis of Compound 3
1) Synthesis of intermediate 4
For 40g of 1-bromo-3-chloro-5-methylbenzene and 75.8g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 72g of intermediate 4 was obtained by recrystallization using the same materials and equivalents as those used for the synthesis of intermediate 1. (yield 72%). MS [ M + H ]]+＝515
2) Synthesis of intermediate 5
For 30g of intermediate 4, 30.5g of 20.9g of 5- (tert-butyl) -N- (3- (tert-butyl) phenyl) - [1,1' -biphenyl]-2-amine 39g of intermediate 5 was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 2. (yield 80%). MS [ M + H ]]+＝840
3) Synthesis of Compound 3
25g of intermediate 5 and 19.9g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then, recrystallization was performed to obtain 8.1g of compound 3 (yield 32%). MS [ M + H ]]+＝849
Synthesis example 4 Synthesis of Compound 4
1) Synthesis of intermediate 5
For 30g of intermediate 4, 23.7g of bis (4- (2-phenylpropan-2-yl) phenyl) amine 36g of intermediate 5 was obtained by recrystallization using the same materials and equivalent as in the synthesis method of intermediate 2. (yield 70%). MS [ M + H ] ]+＝884
2) Synthesis of Compound 4
25g of intermediate 5 and 18.8g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.6g of compound 4 (yield 30%). MS [ M + H ]]+＝892
Synthesis example 5 Synthesis of Compound 5
1) Synthesis of intermediate 6
For 30g of intermediate 4, 24.7g of N- (5- (tert-butyl) - [1,1' -biphenyl]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 39g of intermediate 6 was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 2. (yield 75%). MS [ M + H ]]+＝890
2) Synthesis of Compound 5
25g of intermediate 6 and 18.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.2g of compound 5 (yield 29%). MS [ M + H ]]+＝898
Synthesis example 6 Synthesis of Compound 6
1) Synthesis of intermediate 7
For 30g of intermediate 4, 28.5g of N- (5'- (tert-butyl) - [1,1':3', 1' -terphenyl]-2' -yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine the same materials and equivalents as used for the synthesis of intermediate 2 were used 42g of intermediate 7 were obtained by recrystallization. (yield 75%). MS [ M + H ]]+＝966
2) Synthesis of Compound 6
25g of intermediate 7 and 17.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.6g of compound 6 (yield 30%). MS [ M + H ]]+＝974
Synthesis example 7 Synthesis of Compound 7
1) Synthesis of intermediate 8
For 30g of intermediate 4, 20.4g of N- (4- (tert-butyl) -2-methylphenyl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 33g of intermediate 8 was obtained by recrystallization using the same materials and equivalents as those used for the synthesis of intermediate 2. (yield 68%). MS [ M + H ]]+＝828
2) Synthesis of Compound 7
25g of intermediate 8 and 20.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.7g of compound 7 (yield 31%). MS [ M + H ]]+＝836
Synthesis example 8 Synthesis of Compound 8
1) Synthesis of intermediate 9
20g of 1, 3-dibromo-5-tert-butylbenzene, 55.3g of 3,5,5,8, 8-pentamethyl-N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -5,6,7, 8-tetrahydronaphthalen-2-amine, 16.5g of sodium tert-butoxide, 1.0g of bis (tri-tert-butylphosphine) palladium (0) were added to 400ml of toluene, followed by stirring under reflux for 4 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 41.7g of intermediate 9. (yield 68%). MS [ M + H ] ]+＝938
2) Synthesis of Compound 8
25g of intermediate 9 and 20.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 150 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.8g of compound 8 (yield 31%). MS [ M + H ]]+＝946
Synthesis example 9 Synthesis of Compound 9
1) Synthesis of intermediate 10
For 15g of intermediate 1, 15.8g of N- (5- (tert-butyl) -2 '-fluoro- [1,1' -biphenyl]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 20.3g of intermediate 10 was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 2. (yield 69%). MS [ M + H ]]+＝780
2) Synthesis of Compound 9
15g of intermediate 10 and 11g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 150 ℃ for 4 hours. After the reaction is finished, extraction is carried out, and then, the reaction solution is passed throughRecrystallization afforded 5g of compound 9 (yield 33%). MS [ M + H ]]+＝808
Synthesis example 10 Synthesis of Compound 10
1) Synthesis of intermediate 11
For 40g of 1-bromo-3- (tert-butyl) -5-chlorobenzene, 66.5g of N- (5- (tert-butyl) - [1,1' -biphenyl]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 75g of intermediate 11 was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 1. (yield 80%). MS [ M + H ] ]+＝579
2) Synthesis of intermediate 12
After 40g of intermediate 11, 11.3g of 4-tert-butylaniline, 19.9g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene and refluxed for 1 hour, it was confirmed whether or not the reaction was carried out, 13.2g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was further carried out for 1 hour. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 28.8g of intermediate 12. (yield 52%). MS [ M + H ]]+＝801
3) Synthesis of intermediate 13
25g of intermediate 12 and 20.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 5.5g of intermediate 13 (yield 22%). MS [ M + H ]]+＝809
4) Synthesis of Compound 10
5g of intermediate 16, 1.5g of diphenylamine, 1.2g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, recrystallization was performed to obtain 4.6g of compound 10. (yield 80%). MS [ M + H ]]+＝943
Synthesis example 11 Synthesis of Compound 11
1) Synthesis of intermediate 14
40g of intermediate 4, 17.6g of 5- (tert-butyl) - [1,1' -biphenyl ]After adding 2-amine, 22.4g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphino) palladium (0) to 600ml of toluene and refluxing for 1 hour, it was confirmed whether or not the reaction was carried out, 14.9g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was further carried out for 1 hour. After completion of the reaction, extraction was performed, and then, 45g of intermediate 14 was obtained by recrystallization. (yield 71%). MS [ M + H ]]+＝814
2) Synthesis of intermediate 15
25g of intermediate 14 and 20.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 8.3g of intermediate 15 (yield 33%). MS [ M + H ]]+＝822
3) Synthesis of Compound 11
Mixing 7g ofIntermediate 15, 3.4g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 1.7g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphino) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.4g of compound 11. (yield 74%). MS [ M + H ]]+＝1175
Synthesis example 12 Synthesis of Compound 12
1) Synthesis of intermediate 16
For 40g of 3-bromo-5-chlorophenol, 79.4g of N- (5- (tert-butyl) - [1,1' -biphenyl ]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 70g of intermediate 3- ((5- (tert-butyl) - [1,1' -biphenyl) was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 1]-2-yl) (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amino) -5-chlorophenol. (yield 57%). MS [ M + H ]]+＝539
After 40g of 3- ((5- (tert-butyl) - [1,1' -biphenyl ] -2-yl) (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amino) -5-chlorophenol, 20ml of 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonyl fluoride and 30g of potassium carbonate were added to 400ml of tetrahydrofuran and 200ml of water, and after the reaction was completed for 3 hours, extraction was performed, and then the solution was removed, 58g of intermediate 16 was obtained. (yield 97%).
2) Synthesis of intermediate 17
40g of intermediate 16, 14g of bis (4- (tert-butyl) phenyl) amine, 0.85g of Pd (dba)21.42g of Xphos (2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl) and 48.6g of cesium carbonate were added to 500ml of xylene, followed by stirring under reflux for 24 hours. After completion of the reaction, extraction was carried out, followed by recrystallization to obtain 31g of intermediate 17 (yield)The rate was 78%). MS [ M + H ]]+＝802
3) Synthesis of intermediate 18
25g of intermediate 17 and 20.8g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene, followed by stirring at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.9g of intermediate 18 (yield 31%). MS [ M + H ]]+＝810
4) Synthesis of Compound 12
7g of intermediate 18, 1.5g of diphenylamine-d 5, 2.5g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, 6.2g of compound 12 was obtained by recrystallization. (yield 76%). MS [ M + H ]]+＝948
Synthesis example 13 Synthesis of Compound 13
1) Synthesis of intermediate 19
40g of intermediate 4, 14.3g of dibenzo [ b, d ]]Furan-1-amine, 22.4g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphino) palladium (0) were added to 600ml of toluene, and the mixture was refluxed for 1 hour, and after confirming whether or not the reaction had proceeded, 20.8g of 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene was added to the reflux reaction, and the reflux reaction was further carried out for 1 hour. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 54g of intermediate 19. (yield 82%). MS [ M + H ]]+＝848
2) Synthesis of Compound 13
25g of intermediate 19 and 19.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.5g of compound 13 (yield 30%). MS [ M + H ] ]+＝856
Synthesis example 14 Synthesis of Compound 14
1) Synthesis of intermediate 20
For 40g of intermediate 4, 15.5g of dibenzo [ b, d ]]Thiophene-4-amine 54g of intermediate 20 was obtained by recrystallization using the same materials and equivalents as the synthesis of intermediate 19. (yield 78%). MS [ M + H ]]+＝864
2) Synthesis of Compound 14
25g of intermediate 20 and 19.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.6g of compound 14 (yield 31%). MS [ M + H ]]+＝872
Synthesis example 15 Synthesis of Compound 15
1) Synthesis of intermediate 21
For 40g of intermediate 4, 18.1g of dibenzo [ b, d ]]Furan-4-bromide, 11.6g of 3- (tert-butyl) aniline Using the same materials and equivalent as in the synthetic method of intermediate 19, 50g of meso-form was obtained by recrystallizationAn intermediate 21. (yield 76%). MS [ M + H ]]+＝850
2) Synthesis of Compound 15
25g of intermediate 21 and 21g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 8.3g of compound 15 (yield 31%). MS [ M + H ] ]+＝858
Synthesis example 16 Synthesis of Compound 16
1) Synthesis of intermediate 22
40g of intermediate 4, 14.3g of dibenzo [ b, d ]]Furan-1-amine, 22.4g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphino) palladium (0) were added to 600ml of toluene, and the mixture was refluxed for 1 hour to confirm whether or not the reaction was carried out, and then 14.9g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was further carried out for 1 hour. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 46g of intermediate 22. (yield 77%). MS [ M + H ]]+＝771
2) Synthesis of intermediate 23
25g of intermediate 22 and 21.6g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.8g of intermediate 23 (yield 31%). MS [ M + H ]]+＝780
3) Synthesis of Compound 16
7g of intermediate 23, 1.8g of 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.7g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, 6.1g of compound 16 was obtained by recrystallization. (yield 72%). MS [ M + H ] ]+＝945
Synthesis example 17 Synthesis of Compound 17
1) Synthesis of intermediate 24
For 30g of N- (3-chloro-5- (methyl-d 3) phenyl) -5,5,8, 8-tetramethyl-N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -5,6,7, 8-tetrahydronaphthalen-2-amine, 17.9g of 3,5,5,8, 8-pentamethyl-N- (m-tolyl) -5,6,7, 8-tetrahydronaphthalen-2-amine, 31.3g of intermediate 24 was obtained by recrystallization using the same materials and equivalent as those used for the synthesis of intermediate 2. (yield 69%). MS [ M + H ]]+＝789
2) Synthesis of Compound 17
25g of intermediate 24 and 20.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7g of compound 17 (yield 29%). MS [ M + H ]]+＝797
Synthesis example 18 Synthesis of Compound 18
1) Synthesis of intermediate 25
40g of N-, (5- (tert-butyl) - [1,1' -biphenyl]After (2) -yl) -N- (3-chloro-5-methylphenyl) -1,1,3, 3-tetramethyl-2, 3-dihydro-1H-indene-5-amine, 12.1g of 4- (tert-butyl) -2-methylaniline, 22.1g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene, the mixture was refluxed for 1 hour, and after confirming whether or not the reaction had proceeded, 14.6g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was further carried out for 1 hour. After completion of the reaction, extraction was performed, and then, 43g of intermediate 25 was obtained by recrystallization. (yield 74%). MS [ M + H ] ]+＝760
2) Synthesis of intermediate 26
25g of intermediate 25 and 21.9g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.1g of intermediate 26 (yield 28%). MS [ M + H ]]+＝768
3) Synthesis of Compound 18
7g of intermediate 26, 2.5g of bis (4- (tert-butyl) phenyl) amine, 1.7g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, 6.5g of compound 18 was obtained by recrystallization. (yield 72%). MS [ M + H ]]+＝1013
Synthesis example 19 Synthesis of Compound 19
1) Synthesis of intermediate 28
For 40g of 3-bromo-5-chlorophenol, 75.2g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalene-2-Yl) amine 70g of intermediate 27 was obtained by recrystallization using the same materials and equivalents as for the synthesis of intermediate 35. (yield 70%). MS [ M + H ]]+＝517
The same materials and equivalents as for the synthesis of intermediate 16 were used for 40g of intermediate 27 to obtain 56g of intermediate 28. (yield 92%). MS [ M + H ]]+＝783
2) Synthesis of intermediate 29
For 40g of intermediate 28, 34g of N- (3- (dibenzo [ b, d ]) ]Thien-2-yl) phenyl) -3-methyl- [1,1' -biphenyl]The-4-amine was recrystallized using the same materials and equivalents as the synthesis of intermediate 17 to obtain 54g of intermediate 29. (yield 74%). MS [ M + H ]]+＝940
3) Synthesis of intermediate 30
25g of intermediate 29 and 17.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.5g of intermediate 30 (yield 30%). MS [ M + H ]]+＝948
3) Synthesis of Compound 19
7g of intermediate 30, 2.1g of bis (4- (tert-butyl) phenyl) amine, 1.7g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, 6.6g of compound 19 was obtained by recrystallization. (yield 72%). MS [ M + H ]]+＝1235
Synthesis example 20 Synthesis of Compound 20
1) Synthesis of intermediate 31
99g of intermediate 31 was obtained by recrystallization under a nitrogen atmosphere using the same materials and equivalent as the synthesis method of intermediate 9 for 40g of 1, 3-dibromo-5-chlorobenzene and 115.3g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine. (yield 75%). MS [ M + H ] ]+＝888
2) Synthesis of intermediate 32
25g of intermediate 31 and 18.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.7g of intermediate 32 (yield 31%). MS [ M + H ]]+＝896
3) Synthesis of Compound 20
7g of intermediate 32, 3g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 1.5g of sodium tert-butoxide, 0.04g of bis (tri-tert-butylphosphino) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, recrystallization was performed to obtain 7.1g of compound 20. (yield 73%). MS [ M + H ]]+＝1249
Synthesis example 21 Synthesis of Compound 21
1) Synthesis of intermediate 33
25g of intermediate 33 was obtained by the same method as that for synthesizing intermediate 1 of Synthesis example 1 using 25g of bis (3-isopropylphenyl) amine. (yield 67%). MS [ M + H ]]+＝378
2) Synthesis of intermediate 34
By the same method as that for synthesizing intermediate 2 of Synthesis example 1, using 27.3g of N- (5- (tert-butyl) - [1,1' -biphenyl)]-2-yl) -9,9,10, 10-tetramethyl-9, 10-dihydroanthracen-2-amine to yield 32.2g of intermediate 34. (yield 71%). MS [ M + H ] ]+＝858
3) Synthesis of Compound 21
25g of intermediate 34 and 20.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.3g of compound 21 (yield 29%). MS [ M + H ]]+＝866
Synthesis example 22 Synthesis of Compound 22
1) Synthesis of Compound 22
7g of intermediate 32, 1.93g of 4a,9 a-dimethyl-6-phenyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.52g of sodium tert-butoxide, 0.04g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene under a nitrogen atmosphere, and then stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and then, 6.9g of compound 22 was obtained by recrystallization. (yield 78%). MS [ M + H ]]+＝1137
Synthesis example 23 Synthesis of Compound 23
1) Synthesis of intermediate 36
40.5g of intermediate 36 was obtained by the same method as that for synthesizing intermediate 16 of Synthesis example 12 using 35g of bis ([1,1' -biphenyl ] -3-yl) amine. (yield 51%).
2) Synthesis of intermediate 37
Using 20.4g of N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] by the same method as that for the synthesis of intermediate 17 in Synthesis example 12]Furan-1-amine to yield 31.8g of intermediate 37. (yield 72%). MS [ M + H ] ]+＝799
3) Synthesis of intermediate 38
By the same method as that for synthesizing the intermediate 18 of synthesis example 12, using 30g of the intermediate 37, 11.8g of the intermediate 38 was obtained. (yield 39%). MS [ M + H ]]+＝808
3) Synthesis of Compound 23
By a method similar to that for synthesizing compound 12 of synthesis example 12, using 7g of intermediate 38, 2.4g of 4a,9 a-dimethyl-6- (trimethylsilyl) -2,3,4,4a,9,9 a-hexahydro-1H-carbazole, 6.2g of compound 23 was obtained. (yield 69%). MS [ M + H ]]+＝1045
Synthesis example 24 Synthesis of Compound 24
1) Synthesis of intermediate 39
27.3g of intermediate 39 was obtained by the same method as that for synthesizing intermediate 1 of Synthesis example 1, using 25g of 3' -bromo-5 ' -chloro-2, 6-dimethyl-1, 1' -biphenyl and 23.8g of bis (3- (tert-butyl) phenyl) amine. (yield 65%). MS [ M + H ]]+＝496
2) Synthesis of intermediate 40
23.9g of intermediate 40 was obtained by the same method as that for synthesizing intermediate 2 of Synthesis example 1, using 22g of intermediate 39 and 17.5g of 9, 9-dimethyl-N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-4-amine. (yield 63%). MS [ M + H ]]+＝856
3) Synthesis of Compound 24
By the same method as that for synthesizing compound 11 of synthesis example 1, using 20g of intermediate 39, 4.2g of compound 24 was obtained. (yield 21%). MS [ M + H ] ]+＝864
Synthesis example 25 Synthesis of Compound 25
1) Synthesis of intermediate 41
40g of A1, 69g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 34.1g of sodium tert-butoxide, 0.9g of bis (tri-tert-butylphosphino) palladium (0) were added to 600ml of toluene under a nitrogen atmosphere, followed by stirring at reflux for 2 hours. After the reaction was completed, extraction was performed, and then, 70g was obtained by recrystallizationIntermediate 41 of (1). (yield 74%). MS [ M + H ]]+＝535
2) Synthesis of intermediate 42
40g of intermediate 41, 16.9g of 5- (tert-butyl) - [1,1' -biphenyl were added under nitrogen atmosphere]2-amine, 0.4g of bis (tri-tert-butylphosphine) palladium (0), and 18g of sodium tert-butoxide were added to 600ml of toluene, followed by stirring under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 14.3g of 1-bromo-3-chlorobenzene was added while stirring, and then the mixture was refluxed and stirred for 4 hours. After completion of the reaction, extraction was performed, and then, 45g of intermediate 42 was obtained by recrystallization. (yield 72%). MS [ M + H ]]+＝835
3) Synthesis of intermediate 43
25g of intermediate 42 and 20.0g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.4g of intermediate 43 (yield 29%). MS [ M + H ] ]+＝843
4) Synthesis of Compound 25
7g of intermediate 43, 4.3g of 6- (tert-butyl) -4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.6g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) are added to 100ml of toluene under a nitrogen atmosphere, and then stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.7g of compound 25. (yield 72%). MS [ M + H ]]+＝1284
Synthesis example 26 Synthesis of Compound 26
1) Synthesis of Compound 26
7g of intermediate 4, 1.6g of 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole-5, 6,7,8-d4, 1.6g of sodium tert-butoxide, 0.04g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, 6.5g of compound 26 was obtained by recrystallization. (yield 78%). MS [ M + H ]]+＝1065
Synthesis example 27 Synthesis of Compound 27
1) Synthesis of intermediate 44
40g of A2, 71.9g of N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] are introduced under nitrogen]Furan-4-amine, 37.4g of sodium tert-butoxide, 1.0g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene, followed by stirring under reflux for 2 hours. After completion of the reaction, extraction was performed, and then, 72g of intermediate 44 was obtained by recrystallization. (yield 75%). MS [ M + H ] ]+＝495
2) Synthesis of intermediate 45
40g of intermediate 44, 14.8g of dibenzo [ b, d ] under nitrogen atmosphere]Furan-4-amine, 0.4g of bis (tri-tert-butylphosphine) palladium (0) and 19g of sodium tert-butoxide were added to 600ml of toluene, and then the mixture was stirred under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 15.5g of 1-bromo-3-chlorobenzene was added during the stirring, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and then, 45g of intermediate 45 was obtained by recrystallization. (yield 74%). MS [ M + H ]]+＝752
3) Synthesis of intermediate 46
25g of intermediate 45 and 22.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.7g of intermediate 46 (yield 30%). MS [ M + H ]]+＝760
4) Synthesis of Compound 27
7g of intermediate 46, 2.4g of 6- (tert-butyl) -4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.8g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) are added to 100ml of toluene under a nitrogen atmosphere, and then stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, 6.7g of compound 27 was obtained by recrystallization. (yield 74%). MS [ M + H ] ]+＝981
Synthesis example 28 Synthesis of Compound 28
1) Synthesis of intermediate 47
40g of A2, 71.9g of N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] are introduced under nitrogen]Furan-1-amine, 37.4g of sodium tert-butoxide, 1.0g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene, followed by stirring under reflux for 2 hours. After completion of the reaction, extraction was performed, and then, 73g of intermediate 47 was obtained by recrystallization. (yield 76%). MS [ M + H ]]+＝495
2) Synthesis of intermediate 48
40g of intermediate 47, 16.1g of dibenzo [ b, d ] under nitrogen atmosphere]Thiophene-4-amine, 0.4g bis (three tert butyl phosphine) palladium (0) into 600ml toluene, reflux stirring for 1 hours. Then, after confirming whether or not the reaction was carried out, 15.5g of 1-bromo-3-chlorobenzene was added during the stirring, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, extraction was performed, and then, 44g of intermediate 48 was obtained by recrystallization. (yield 71%). MS [ M + H ]]+＝768
3) Synthesis of intermediate 49
25g of intermediate 48 and 21.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.4g of intermediate 49 (yield 29%). MS [ M + H ] ]+＝776
4) Synthesis of Compound 28
7g of intermediate 49, 2.1g of 4a,5,7,9 a-tetramethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.8g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, 6.8g of compound 28 was obtained by recrystallization. (yield 78%). MS [ M + H ]]+＝969
Synthesis example 29 Synthesis of Compound 29
1) Synthesis of intermediate 50
Under nitrogen atmosphere, the mixture is20g of 1, 3-dibromo-5-chlorobenzene, 41.6g of bis (4- (tert-butyl) phenyl) amine, 35.5g of sodium tert-butoxide, and 0.4g of bis (tri-tert-butylphosphine) palladium (0) were added to 300ml of toluene, followed by stirring under reflux for 2 hours. After completion of the reaction, extraction was performed, and then, 35g of intermediate 50 was obtained by recrystallization. (yield 70%). MS [ M + H ]]+＝672
2) Synthesis of intermediate 51
25g of intermediate 50 and 24.8g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.4g of intermediate 51 (yield 29%). MS [ M + H ]]+＝680
3) Synthesis of Compound 29
7g of intermediate 51, 2.1g of 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 2.0g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) are added to 100ml of toluene under a nitrogen atmosphere, and then stirred under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, 6.8g of compound 29 was obtained by recrystallization. (yield 78%). MS [ M + H ] ]+＝845
Synthesis example 30 Synthesis of Compound 30
By the same method as that for producing intermediate 5 of synthesis example 3, using 15g of bis (4-cyclohexylphenyl) amine, 26.6g of intermediate 52 was obtained. (yield 73%). MS [ M + H ]]+＝812
Using 20g of the same method as that for the production of Compound 3 of Synthesis example 3Intermediate 52 to yield 9.2g of compound 30. (yield 46%). MS [ M + H ]]+＝820
Synthesis example 31 Synthesis of intermediate 53
The starting material B1(20g, 1 eq.), bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydro-naphthalen-2-yl) amine (35.6g, 2.05 eq.), Pd (PtBu) were charged3)2A flask of (1.1g, 0.05 eq), NaOtBu (12.8g, 3 eq), and toluene (250ml) was heated at 110 ℃ and stirred for 6 hours. The reaction solution was cooled to room temperature, water and toluene were added, and after liquid separation, the solvent was distilled off under reduced pressure. Purification by recrystallization (toluene/hexane) gave intermediate 53(30.9 g). (yield 65%). MS [ M + H ]]+＝1066
Synthesis example 32 Synthesis of Compound 31
To a flask containing intermediate 53(25g) and toluene (150ml) was added a solution of n-butyllithium pentane (18.7ml, 2.5M in hexane (2.5M in hexane, 2 equiv.) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 50 ℃ and stirred for 2 hours. Cooled to-40 ℃, boron tribromide (3.4ml, 1.5 equivalents) was added, warmed to room temperature, and stirred for 4 hours. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (10ml) was added, and the reaction solution was further stirred at room temperature for 30 minutes. A NaCl saturated solution (sat. aq. NaCl) and ethyl acetate were added, and after liquid separation, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (toluene/hexane), whereby compound 31(6.3g) was obtained. (yield 27%). MS [ M + H ] ]+＝996
Synthesis example 33 Synthesis of Compound 2-1
1) Synthesis of intermediate 55
Intermediate 54(41g, yield 63%) was produced by the same method as that for the synthesis of intermediate 53 in synthesis example 31 using the starting material of the above formula. MS [ M + H ]]+＝623
Intermediate 55(7.5g, yield 49%) was obtained using 15g of intermediate 54 by the same method as that for the production of compound 3 of synthesis example 3. MS [ M + H ]]+＝631
2) Synthesis of Compound 2-1
By a method similar to the method for synthesizing compound 29 of synthesis example 29, compound 2-1(8.6g, yield 77%) was obtained using the starting material of the above formula. MS [ M + H ]]+＝778
Synthesis example 34 Synthesis of Compound 2-2
1) Synthesis of intermediate 72
40g of A2, 50.1g of 6- (tert-butyl) -4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.0g of bis (tri-tert-butylphosphine) palladium (0) and 38g of sodium tert-butoxide were added to 600ml of toluene under a nitrogen atmosphere, and then stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by column purification to obtain 52g of intermediate 72. (yield 70%). MS [ M + H ]]+＝383
2) Synthesis of intermediate 57
Obtained by a similar method to that for the synthesis of intermediate 48 in Synthesis example 28, using the starting material of the above formula Intermediate 56(39.5g, 59% yield) was obtained. MS [ M + H ]]+＝695
Intermediate 57(8.5g, yield 44%) was obtained using 19g of intermediate 56 by the same method as that for producing compound 3 of synthesis example 3. MS [ M + H ]]+＝703
3) Synthesis of Compound 2-2
By a method similar to the method for synthesizing compound 29 of synthesis example 29, compound 2-2(6.9g, yield 71%) was obtained using the starting material of the above formula. MS [ M + H ]]+＝865
Synthesis example 35 Synthesis of Compound 2-3
1) Synthesis of intermediate 73
40g of intermediate 72, 20.9g of dibenzo [ b, d ] under nitrogen atmosphere]Thiophene-4-amine, 0.6g bis (three tert butyl phosphine) palladium (0), 25.2g tert butyl alcohol sodium into 600ml toluene, reflux stirring for 1 hours. Then, after confirming whether or not the reaction was carried out, 20.1g of 1-bromo-3-chlorobenzene was added during the stirring, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and then, recrystallization was performed to obtain 54g of intermediate 73. (yield 79%). MS [ M + H ]]+＝656
2) Synthesis of intermediate 74
25g of intermediate 73 and 25.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.4g of intermediate 74 (yield 29%). MS [ M + H ] ]+＝664
2) Synthesis of Compounds 2-3
By a method similar to the method for synthesizing compound 29 of synthesis example 29, using the starting material of the above formula, compound 2-3(6.9g, yield 74%) was obtained. MS [ M + H ]]+＝886
Synthesis example 36 Synthesis of Compounds 2 to 4
1) Synthesis of intermediate 58
The starting material of the above formula was used to obtain intermediate 58(32g, yield 76%) by the same method as that for the synthesis of intermediate 72 of synthesis example 34. MS [ M + H ]]+＝410
2) Synthesis of intermediate 60
By a method similar to that for the synthesis of intermediate 48 in synthesis example 28, starting material of the above formula was used to obtain intermediate 59(20.7g, yield 62%). MS [ M + H ]]+＝701
Intermediate 60(5.8g, yield 38%) was obtained using 15g of intermediate 59 in the same manner as in the production of compound 3 of synthesis example 3. MS [ M + H ]]+＝709.44
3) Synthesis of Compounds 2-4
A compound was obtained by the same method as that for synthesizing Compound 29 of Synthesis example 29 using the starting material of the above formulaProduct 2-4(4.4g, 66% yield). MS [ M + H ]]+＝949
Synthesis example 37 Synthesis of Compounds 2 to 5
1) Synthesis of intermediate 62
By a method similar to the method for synthesizing intermediate 72 of synthesis example 34, intermediate 61(26g, yield 79%) was obtained using the starting material of the above formula. MS [ M + H ] ]+＝396
By a method similar to the method for synthesizing intermediate 34 of synthesis example 21, intermediate 62(15.9g, yield 67%) was obtained using the starting material of the above formula. MS [ M + H ]]+＝691
2) Synthesis of Compounds 2-5
Compound 2-5(5g, yield 35%) was obtained by the same method as that for the production of compound 3 of synthesis example 3 using 14g of intermediate 62. MS [ M + H ]]+＝699
Synthesis example 38 Synthesis of Compounds 2 to 6
1) Synthesis of intermediate 64
By a method similar to the method for synthesizing intermediate 72 of synthesis example 34, intermediate 63(26.3g, yield 76%) was obtained using the starting material of the above formula. MS [ M + H ]]+＝424
The starting material of the above formula was used to obtain intermediate 64(29.8g, yield 70%) by the same method as that for synthesizing intermediate 34 of synthesis example 21. MS [ M + H ]]+＝754
2) Synthesis of Compounds 2-6
By a method similar to the method for producing compound 3 of synthesis example 3, 19g of intermediate 64 was used to obtain compounds 2 to 6(7.5g, yield 39%). MS [ M + H ]]+＝761
Synthesis example 39 Synthesis of Compounds 2 to 7
1) Synthesis of intermediate 68
40g of A2, 39.2g of 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole, 1.0g of bis (tri-tert-butylphosphine) palladium (0) and 38g of sodium tert-butoxide were added to 600ml of toluene under a nitrogen atmosphere, and then stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by column purification to obtain 49g of intermediate 68. (yield 77%). MS [ M + H ] ]+＝326
2) Synthesis of intermediate 69
Under nitrogen atmosphere, 40g of intermediate 68, 22.5g of dibenzo [ b, d ] are added]Furan-1-amine, 0.6g of bis (tri-tert-butylphosphine) palladium (0) and 29.5g of sodium tert-butoxide were added to 600ml of toluene, and then the mixture was stirred under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 23.5g of 1-bromo-3-chlorobenzene was added while stirring, and then the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and then, 55g of intermediate 69 was obtained by recrystallization. (yield 77%). MS [ M + H ]]+＝584
3) Synthesis of Compounds 2-7
25g of intermediate 69 and 28.5g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.8g of intermediate 70 (yield 31%). MS [ M + H ]]+＝592
7g of intermediate 70, 3.4g of bis (4- (tert-butyl) phenyl) amine, 2.3g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.4g of compounds 2 to 7. (yield 75%). MS [ M + H ]]+＝836
Synthesis example 40 Synthesis of Compounds 2 to 8
1) Synthesis of intermediate 71
Under nitrogen atmosphere, 40g of intermediate 68, 22.5g of dibenzo [ b, d ] are added]Furan-4-amine, 0.6g of bis (tri-tert-butylphosphine) palladium (0) and 29.5g of sodium tert-butoxide were added to 600ml of toluene, and then the mixture was stirred under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 23.5g of 1-bromo-3-chlorobenzene was added while stirring, and then the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was carried out to obtain 54g of intermediate 71. (yield 76%). MS [ M + H ]]+＝584
2) Synthesis of Compounds 2 to 8
25g of intermediate 71 and 28.5g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.6g of intermediate 72 (yield 30%). MS [ M + H ]]+＝592
Under nitrogen atmosphere, 7g of intermediate 72, 3.4g of bis (4- (tert-butyl) phenyl)) Amine, 2.3g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.6g of compounds 2 to 8. (yield 76%). MS [ M + H ]]+＝836
Synthesis example 41 Synthesis of Compounds 2 to 9
1) Synthesis of Compounds 2-9
7g of intermediate 72, 4.6g of bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 2.3g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphino) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.5g of compounds 2 to 9. (yield 76%). MS [ M + H ]]+＝945
Synthesis example 42 Synthesis of Compounds 2 to 10
1) Synthesis of Compounds 2-10
7g of intermediate 74, 3.5g of bis (4- (tert-butyl) phenyl) amine, 2.1g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.5g of compounds 2 to 10. (yield 78%). MS [ M + H ]]+＝909
Synthesis example 43 Synthesis of Compounds 2 to 11
1) Synthesis of intermediate 75
Under nitrogen atmosphere, 40g of A1, 35.7g of 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexaHydrogen-1H-carbazole, 0.9g of bis (tri-t-butylphosphino) palladium (0), and 34g of sodium t-butoxide were added to 600ml of toluene, followed by stirring under reflux for 4 hours. After completion of the reaction, extraction was performed, followed by column purification to obtain 47g of intermediate 75. (yield 77%). MS [ M + H ] ]+＝347
2) Synthesis of intermediate 76
40g of intermediate 75, 21.2g of dibenzo [ b, d ] under nitrogen]Furan-4-amine, 0.6g of bis (tri-tert-butylphosphine) palladium (0) and 27.8g of sodium tert-butoxide were added to 600ml of toluene, and then the mixture was stirred under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 22.1g of 1-bromo-3-chlorobenzene was added while stirring, and then the mixture was refluxed and stirred for 4 hours. After completion of the reaction, extraction was performed, and then, 55g of intermediate 76 was obtained by recrystallization. (yield 79%). MS [ M + H ]]+＝604
3) Synthesis of Compounds 2-11
25g of intermediate 76 and 27.6g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.2g of intermediate 77 (yield 28%). MS [ M + H ]]+＝612
7g of intermediate 77, 6.5g of bis (4- (tert-butyl) phenyl) amine, 2.1g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, recrystallization was carried out to obtain 7.9g of compounds 2 to 11. (yield 63%). MS [ M + H ]]+＝1102
Synthesis example 44 Synthesis of Compounds 2 to 12
1) Synthesis of intermediate 78
40g of intermediate 72, 21.6g of 3,5,5,8, 8-pentamethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, 0.5g of bis (tri-tert-butylphosphino) palladium (0) and 23.9g of sodium tert-butoxide are added to 600ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 1 hour. Then, after confirming whether or not the reaction was carried out, 19.1g of 1-bromo-3-chlorobenzene was added while stirring, and then the mixture was refluxed and stirred for 4 hours. After completion of the reaction, extraction was performed, and then, 53g of intermediate 78 was obtained by recrystallization. (yield 77%). MS [ M + H ]]+＝694
2) Synthesis of Compounds 2-12
25g of intermediate 78 and 24.0g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under a nitrogen atmosphere, and the mixture was stirred at 160 ℃ for 4 hours. After completion of the reaction, extraction was performed, and then recrystallization was performed to obtain 7.4g of intermediate 79 (yield 29%). MS [ M + H ]]+＝702
7g of intermediate 79, 5.6g of bis (4- (tert-butyl) phenyl) amine, 2.0g of sodium tert-butoxide, and 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under a nitrogen atmosphere, followed by stirring under reflux for 6 hours. After completion of the reaction, extraction was performed, and then, 8.3g of compounds 2 to 12 was obtained by recrystallization. (yield 70%). MS [ M + H ]]+＝1192
Synthesis example 45 Synthesis of Compounds 2 to 13
22g of intermediate 80 was obtained by the same method as that for synthesizing intermediate 17 of synthesis example 12, using intermediate 28 and 4a,5,7,9 a-tetramethyl-6-phenyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole. (yield 61%). MS [ M + H ]]+＝804
By a method similar to the method for producing compound 3 of synthesis example 3, 20g of intermediate 80 was used to obtain intermediate 81(5.9g, 29%). MS [ M + H ]]+＝811
By a method similar to the method for synthesizing compound 29 of synthesis example 29, using the starting materials of the above formula, compound 2-13(5.4g, yield 68%) was obtained. MS [ M + H ]]+＝1097
Synthesis example 46 Synthesis of Compound 32
The substance of the above formula was used to obtain 16.3g of intermediate 82 by the same method as that for producing intermediate 5 of synthesis example 3. (yield 77%). MS [ M + H ]]+＝647
By the same method as that for the production of compound 3 of synthesis example 3, 16g of intermediate 82 was used to obtain 5.3g of compound 32. (yield 33%). MS [ M + H ]]+＝655
Synthesis example 47 Synthesis of Compound 33
1) Synthesis of intermediate 84
32g of intermediate 83 was obtained using the substance of the above formula by the same method as that for producing intermediate 31 of Synthesis example 20. (yield 71%). MS [ M + H ] ]+＝663
10g of intermediate 84 was obtained using the substance of the above formula by the same method as that for producing intermediate 32 of Synthesis example 20. (yield: 32%). MS [ M + H ]]+＝671
2) Synthesis of Compound 33
8.5g of compound 33 was obtained using the substance of the above formula by the same method as that for producing compound 20 of Synthesis example 20. (yield 70%). MS [ M + H ]]+＝913
The present specification also provides a method for manufacturing an organic light-emitting device using the heterocyclic compound.
Synthesis example 48.
20g of the compound 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine A2-1, 27g of B-1, 21g of potassium carbonate [ potassium carbonate ] were added]380mL of tetrahydrofuran and 50mL of water, 1.1g of tetrakis (triphenylphosphine) palladium (0) [ tetrazolis (triphenylphosphinothhine) palladium (0)]Pd(PPh3)4After that, the mixture was stirred with heating for 8 hours. After the reaction, the reaction mixture was cooled to room temperature, the organic solvent was removed, and the organic solvent was dissolved in toluene and extracted, followed by dissolving the organic solvent with MgSO4(anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/ethyl acetate), whereby 26g of compound E1 was obtained. (yield 82%, Mass [ M +) ]＝613)
Synthesis example 49.
18g of intermediate 2-1 was obtained by the same method as the synthetic method for Compound E1 in synthetic example 48, except that 16g of B-2 was used instead of starting material B-1. (yield 77%, Mass [ M + ] ═ 452)
A charge of 18g of intermediate 2-1, 23g of potassium carbonate, 10.7mL of perfluorobutanesulfonyl fluoride [ perfluorobutanesulfonyl fluoride ] was charged]And a 180mL flask of Dimethylformamide (DMF) were stirred at room temperature for 1 hour. After the reaction was completed, water was added to the reaction solution, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in toluene and then NH was added4Cl solution (aq. NH)4Cl), extracted and then MgSO4(anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane), thereby obtaining 24g of intermediate 2-2. (yield 82%, Mass [ M +)]＝734)
Prepared by the same method as the synthesis method of compound E1 of Synthesis example 48 except that 24g of intermediate 2-2 was used instead of A2-1 and 8.8g of B-3 was used instead of B-1, to obtain 15g of E2. (yield 75%, Mass [ M + ]. 613)
Synthesis example 50.
17g of intermediate 2-4 was obtained by the same method as the synthetic method of Compound E1 in synthetic example 34, except that 16.7g of B-4 was used instead of B-1. (yield 74%, Mass [ M + ]. 452)
22g of intermediate 2-5 was obtained by the same method as the synthesis method of intermediate 2-2 in Synthesis example 49, except that 17g of intermediate 2-4 was used instead of intermediate 2-1. (yield 80%, Mass [ M + ]. 734)
14g of E3 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 22g of intermediate 2-5 was used in place of A2-1 and 6.2g of B-5 was used in place of B-1. (yield 76%, Mass [ M + ]. 613)
Synthesis example 51.
Preparation was carried out in the same manner as the synthetic method of Compound E1 of Synthesis example 34 except that 20g of A2-2 was used in place of A2-1 and 19.6g of B-6 was used in place of B-1, to obtain 16g of intermediate 2-6. (yield 84%, Mass [ M + ] ═ 271)
Preparation was carried out in the same manner as the synthetic method of Compound E1 of synthetic example 48 except that 16g of intermediate 2-6 was used in place of A2-1 and 15.8g of B-3 was used in place of B-1, whereby 25g of E4 was obtained. (yield 79%, Mass [ M + ] -536)
Synthesis example 52.
27g of E5 was obtained by the same method as the method for synthesizing the compound E1 in Synthesis example 48, except that 20g of A2-3 was used in place of A2-1 and 17.2g of B-7 was used in place of B-1. (yield 77%, Mass [ M + ] ═ 526)
Synthesis example 53.
The preparation was carried out in the same manner as the synthesis method of Compound E1 in Synthesis example 48, except that 10g of A2-4 was used in place of A2-1 and 15g of B-8 was used in place of B-1, whereby 16g of intermediates 2 to 7 were obtained. (yield 81%, Mass [ M + ] -599)
15g of E6 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 16g of intermediate 2-7 was used in place of A2-1 and 7.2g of B-3 was used in place of B-1. (yield 76%, Mass [ M + ]. 741)
Synthesis example 54.
The preparation was carried out in the same manner as the synthetic method of Compound E1 in Synthesis example 48 except that 10g of A2-4 was used in place of A2-1 and 15.6g of B-9 was used in place of B-1, whereby 16g of intermediates 2 to 8 were obtained. (yield 79%, Mass [ M + ] ═ 615)
Prepared by the same method as the synthetic method of compound E1 of synthetic example 48 except that 16g of intermediate 2-8 was used instead of A2-1 and 7.0g of B-3 was used instead of B-1, thereby obtaining 16g of E7. (yield 81%, Mass [ M + ]. 757)
Synthesis example 55.
The preparation was carried out in the same manner as the synthesis method of Compound E1 in Synthesis example 48, except that 20g of A2-5 was used in place of A2-1 and 20.5g of B-9 was used in place of B-1, whereby 23g of intermediates 2 to 9 were obtained. (yield 74%, Mass [ M + ]. 642)
26g of intermediate 2-10 was obtained by the same method as the synthesis method of intermediate 2-2 in Synthesis example 49, except that 23g of intermediate 2-9 was used instead of intermediate 2-1. (yield 79%, Mass [ M + ]. 924)
15g of E8 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 26g of intermediate 2-10 was used in place of A2-1 and 5.0g of B-10 was used in place of B-1. (yield 73%, Mass [ M + ] -727)
Synthesis example 56.
26g of E9 was obtained by a method similar to the synthesis method of Compound E1 in Synthesis example 48, except that 26g of B-11 was used in place of B-1. (yield 84%, Mass [ M + ]. 603)
Synthesis example 57.
25g of E10 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 20g of A2-6 was used in place of A2-1 and 28.9g of B-12 was used in place of B-1. (yield 78%, Mass [ M + ]. 725)
< device example 1>
Example 1
ITO (indium tin oxide) is added
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HI-A compound was added
The following HAT compounds were added to
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, the following HT-A compound
Performing vacuum evaporationThereby forming a hole transport layer.
Then, on the hole transport layer, the film thickness
The following BH-a compound (host) and compound 1 (dopant) were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the compound E1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form a layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 2 to 19 and comparative examples 1 to 7
An organic light-emitting device was produced in the same manner as in example 1, except that the dopant material of the light-emitting layer and the electron injection/transport layer material were each as described in table 1 below.
For the organic light emitting devices of the above examples 1 to 19 and comparative examples 1 to 7, at 10mA/cm2The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm2The time (T95) until the initial luminance reached 95% was measured at the current density of (a), and the relative value was shown based on comparative example 1. The results are shown in table 1 below.
[ Table 1 ]
From the above table 1, it is known that an organic light emitting device including the compound of chemical formula 1 or 2 of the present invention as a dopant of a light emitting layer and the compound of chemical formula 3 of the present invention as an electron injecting and transporting layer is excellent in high efficiency and/or long life characteristics.
< device example 2>
Example 20
ITO (indium tin oxide) is added
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, a product of Hill corporation was used as the detergent, and distilled water obtained by twice filtration using a filter manufactured by Millipore corporation was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. Further, the substrate was cleaned by oxygen plasma After 5 minutes of washing, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HI-A compound was added
The following HAT compounds were added to
The hole injection layer is formed by sequentially performing thermal vacuum deposition. On the hole injection layer, the following HT-A compound
Vacuum evaporation is performed to form a hole transport layer. On the hole transport layer, the following HT-B and
the electron blocking layer is formed by vacuum evaporation.
Then, on the hole transport layer, the film thickness
The light-emitting layer was formed by vacuum vapor deposition of a BH — B compound (host) and a compound 22 (dopant) at a weight ratio of 25: 1.
On the light-emitting layer, compound E1 was vacuum-deposited to form a layer
Forming a hole blocking layer. Vacuum vapor deposition was performed on the hole-blocking layer at a weight ratio of 1:1 of the compound ET-E and the LiQ compound to form a hole-blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4 
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 21 to 38 and comparative examples 8 to 14
An organic light-emitting device was produced in the same manner as in example 20, except that the dopant material and the hole-blocking layer material of the light-emitting layer were the materials described in table 2 below.
For the organic light emitting devices of the above examples 20 to 38 and comparative examples 8 to 14, at 10mA/cm2The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm2The time (T95) until the initial luminance reached 95% was measured at the current density of (a), and the relative value was shown based on comparative example 8. The results are shown in table 2 below.
[ Table 2]
From the above table 2, it is understood that the organic light emitting device including the compound of chemical formula 1 or 2 of the present invention as a dopant of the light emitting layer and the compound of chemical formula 3 of the present invention as a hole blocking layer is excellent in high efficiency and/or long life characteristics.
< element example 3>
Example 39
ITO (indium tin oxide) is added
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, a product of Hill corporation was used as the detergent, and distilled water obtained by twice filtration using a filter manufactured by Millipore corporation was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HI-A compound was added
The following HAT compounds were added to
The hole injection layer is formed by sequentially performing thermal vacuum deposition. On the hole injection layer, the following HT-A compound
Vacuum evaporation is performed to form a hole transport layer. On the hole transport layer, the following HT-B and
the electron blocking layer is formed by vacuum evaporation. Then, on the hole transport layer, the film thickness
The light-emitting layer was formed by vacuum vapor deposition of a BH — C compound (host) and a compound 3 (dopant) at a weight ratio of 25: 1.
On the light-emitting layer, compound E1 was vacuum-deposited to form a layer
Forming a hole blocking layer. On the hole-blocking layer, compound E7 and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1 to obtain a positive hole-blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance 
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 40 to 47 and comparative examples 15 to 17
An organic light-emitting device was produced in the same manner as in example 39, except that the dopant substance, the hole-blocking layer substance, and the electron injection and transport layer substance of the light-emitting layer were each as described in table 3 below.
For the organic light emitting devices of examples 39 to 47 and comparative examples 15 to 17 described above, at 10mA/cm2The driving voltage and the luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm2The time (T95) until the initial luminance reached 95% was measured at the current density of (a), and the relative value was shown based on comparative example 15. The results are shown in table 3 below.
[ Table 3]
From the above table 3, it is known that the organic light emitting device including the compound of chemical formula 1 or 2 of the present invention as a dopant of the light emitting layer and the compound of chemical formula 3 of the present invention as a hole blocking layer, and an electron injection and transport layer is excellent in low voltage, high efficiency, and/or long life characteristics.
Claims (17)
1. An organic light emitting device comprising:
a first electrode;
a second electrode; and
An organic material layer between the first electrode and the second electrode,
wherein the organic layer includes a first organic layer including a compound represented by the following chemical formula 1 or 2 and a second organic layer including a compound represented by the following chemical formula 3:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
ar1 to Ar4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
a1, A2, R1 to R3, Z1 and Z2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
n1 to n3 are each an integer of 0 to 3, and when n1 to n3 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
p1 is 0 or 1 and,
chemical formula 2
In the chemical formula 2,
e1 to E3, which are the same or different from each other, are each independently an aromatic hydrocarbon ring,
1 or more of R4 to R8 are represented by the following chemical formula 1-a or 1-B, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others, which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
n4 and n5 are each an integer of 0 to 4, n6 is an integer of 0 to 3, n7 and n8 are each an integer of 0 to 5,
n4+ n5+ n6+ n7+ n8 is 1 or more,
when n4 to n8 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
chemical formula 1-A
Chemical formula 1-B
In the chemical formulas 1-A and 1-B,
t1 to T17 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
ar11 to Ar14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
L11 is a direct bond or a substituted or unsubstituted arylene group,
p2 is 0 or 1 and,
represents a position to which chemical formula 2 is bound,
chemical formula 3
In the chemical formula 3, the first and second organic solvents,
HAr is a substituted or unsubstituted N-containing heterocyclic group,
l21 and L22, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted 2-to 4-valent aryl group, or a substituted or unsubstituted 2-to 4-valent heterocyclic group,
ar21 is a substituted or unsubstituted arylene group, a substituted or unsubstituted 2-valent heterocyclic group, or-O-,
a and b are each an integer of 1 to 3,
when a is 2 or more, the hars may be the same or different from each other.
2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 101 or 102:
in the chemical formulae 101 and 102,
a1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are as defined in said chemical formula 1,
g1 to G4 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
G11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
g11 is an integer of 0 to 8, and when G11 is 2 or more, 2 or more G11 s are the same as or different from each other,
p3 is 0 or 1.
3. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 103 to 106:
in the chemical formulae 103 to 106,
r1 to R3, Z1, Z2, p1, Ar1 to Ar4 and n1 to n3 are as defined in chemical formula 1,
a3, A4, and G5 through G8 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
Z3, Z4, G12 and G13 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
g12 is an integer of 0 to 8, g13 is an integer of 0 to 4, and when g12 and g13 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other,
p4 and p5 are each 0 or 1.
4. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4:
in the chemical formulas 1-1 to 1-4,
r1 to R3, n1 to n3 and Ar1 to Ar4 are as defined in said chemical formula 1,
a3 and A4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
Z1 to Z4 and Ar21 to Ar24 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring.
5. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 201 to 203:
chemical formula 203
In the chemical formulae 201 to 203,
e1 to E3, n4 to n8 are as defined in chemical formula 2,
r4 to R8, R11 and R12, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring,
p6 and p7 are each 1 or 2,
n5 'is an integer of 0 to 2, n 8' is an integer of 0 to 3, n11 and n12 are each an integer of 0 to 8,
when n5 ', n 8', n11 and n12 are each 2 or more, the substituents in parentheses of 2 or more are the same as or different from each other.
6. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 204:
chemical formula 204
In the chemical formula 204, the chemical formula is shown,
1 or more of R21 to R25 are represented by chemical formula 1-a or 1-B, and the others are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to each other to form a substituted or unsubstituted ring,
e1 to E3, n4 to n8, chemical formula 1-A and 1-B are as defined in the chemical formula 2.
7. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 211 to 219:
chemical formula 219
In the chemical formulae 211 to 219,
n4 to n8 are the same as defined in the chemical formula 2,
r4 to R8 and R11 to R14 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
p6 to p9 are each 1 or 2,
n4 'and n 5' are each an integer of 0 to 2, n7 'and n 8' are each an integer of 0 to 3, n11 to n14 are each an integer of 0 to 8,
when n4 ', n 5', n7 ', n 8' and n11 to n14 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other.
8. The organic light-emitting device according to claim 1, wherein 1 or more of R4 to R8 combine with an adjacent group to form an aliphatic hydrocarbon ring,
1 or more of the aliphatic hydrocarbon rings are represented by any one of the following chemical formulae Cy1 to Cy 3:
in the formulas Cy1 to Cy3,
r31 to R40, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group,
r41 to R43 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
n41 is an integer of 0 to 2, n42 and n43 are each an integer of 0 to 4,
when n41 to n43 are each 2 or more, 2 or more substituents in parentheses are the same as or different from each other.
9. The organic light emitting device according to claim 1, wherein the chemical formula 1-a is represented by the following chemical formula 1-a-1 or 1-a-2, and the chemical formula B-1 is represented by the following chemical formula 1-B-1 or 1-B-2:
chemical formula 1-A-1
Chemical formula 1-A-2
Chemical formula 1-B-1
Chemical formula 1-B-2
In the chemical formulas 1-A-1 and 1-A-2, L11 is as defined in the chemical formula 1-A,
in the chemical formulas 1-B-1 and 1-B-2, T12 to T17 and p2 are defined the same as those in the chemical formula 1-B,
t18 to T21 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group,
t22 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to each other to form a substituted or unsubstituted ring,
When T22 is an integer of 0 to 8 and T22 is 2 or more, 2 or more T22 s are the same as or different from each other.
10. The organic light emitting device according to claim 1, wherein-L22- (CN) of the chemical formula 2bSelected from the following structures:
in the above-described structure, the first and second electrodes are formed on the substrate,
l23 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
r51 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n51 is an integer of 0 to 4, n51' is an integer of 0 to 3,
the dotted line is the position of attachment to said Ar 21.
11. The organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following compounds:
12. the organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 2 is represented by any one of the following compounds:
13. the organic light emitting device according to claim 1, wherein the chemical formula 3 is represented by any one of the following compounds:
14. the organic light-emitting device according to claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the first organic layer is a light-emitting layer, and the second organic layer is provided between the second electrode and the first organic layer.
15. The organic light emitting device according to claim 1, wherein the organic layer comprises 2 or more light emitting layers, and 1 layer of the 2 or more light emitting layers contains the compound represented by chemical formula 1 or 2.
16. The organic light-emitting device according to claim 1, wherein the second organic layer further comprises 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.
17. The organic light emitting device according to claim 1, wherein the second organic layer comprises 1 or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.
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| WO2023246448A1 (en) * | 2022-06-22 | 2023-12-28 | 广东阿格蕾雅光电材料有限公司 | Organic electroluminescent material and use thereof in electroluminescent device |
| CN117362274A (en) * | 2023-12-07 | 2024-01-09 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
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| CN113307764B (en) * | 2021-05-08 | 2023-07-28 | 烟台显华化工科技有限公司 | Compound, electron transport material, organic electroluminescent device and display device |
| EP4151697A1 (en) * | 2021-09-17 | 2023-03-22 | Idemitsu Kosan Co., Ltd. | Compound and an organic electroluminescence device comprising the compound |
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| CN107108408A (en) * | 2015-10-26 | 2017-08-29 | 株式会社Lg化学 | Spiral shell ring-based compounds and the organic illuminating element comprising it |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
| KR101990818B1 (en) * | 2018-05-04 | 2019-06-19 | 머티어리얼사이언스 주식회사 | Organic electroluminescent device |
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| CN110838555B (en) * | 2015-04-24 | 2022-03-08 | 株式会社Lg化学 | Organic light emitting device |
| US11723263B2 (en) * | 2016-04-26 | 2023-08-08 | Kwansei Gakuin Educational Foundation | Organic electroluminescent element |
| WO2018203666A1 (en) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | Novel compound and organic light emitting device using same |
| KR101876763B1 (en) * | 2017-05-22 | 2018-07-11 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising the same |
| CN107417715A (en) * | 2017-07-14 | 2017-12-01 | 瑞声科技（南京）有限公司 | A kind of electroluminescent organic material and its luminescent device |
| KR102112411B1 (en) * | 2017-09-28 | 2020-05-18 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
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| CN107108408A (en) * | 2015-10-26 | 2017-08-29 | 株式会社Lg化学 | Spiral shell ring-based compounds and the organic illuminating element comprising it |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
| KR101990818B1 (en) * | 2018-05-04 | 2019-06-19 | 머티어리얼사이언스 주식회사 | Organic electroluminescent device |
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| WO2023246448A1 (en) * | 2022-06-22 | 2023-12-28 | 广东阿格蕾雅光电材料有限公司 | Organic electroluminescent material and use thereof in electroluminescent device |
| CN117362274A (en) * | 2023-12-07 | 2024-01-09 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
| CN117362274B (en) * | 2023-12-07 | 2024-03-26 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
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| WO2021020946A1 (en) | 2021-02-04 |
| KR102391296B1 (en) | 2022-04-27 |
| CN113646915B (en) | 2024-03-19 |
| KR20210015722A (en) | 2021-02-10 |
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