CN113646915B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN113646915B CN113646915B CN202080026781.5A CN202080026781A CN113646915B CN 113646915 B CN113646915 B CN 113646915B CN 202080026781 A CN202080026781 A CN 202080026781A CN 113646915 B CN113646915 B CN 113646915B
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 452
- 229910052805 deuterium Inorganic materials 0.000 claims description 452
- 239000010410 layer Substances 0.000 claims description 381
- 239000000126 substance Substances 0.000 claims description 276
- 125000003118 aryl group Chemical group 0.000 claims description 231
- 229910052739 hydrogen Inorganic materials 0.000 claims description 213
- 239000001257 hydrogen Substances 0.000 claims description 213
- 125000000217 alkyl group Chemical group 0.000 claims description 202
- 150000002431 hydrogen Chemical class 0.000 claims description 182
- 150000001875 compounds Chemical class 0.000 claims description 170
- 125000000623 heterocyclic group Chemical group 0.000 claims description 157
- 125000001424 substituent group Chemical group 0.000 claims description 152
- 125000005843 halogen group Chemical group 0.000 claims description 140
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 139
- 239000012044 organic layer Substances 0.000 claims description 77
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000003277 amino group Chemical group 0.000 claims description 59
- 125000004104 aryloxy group Chemical group 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000004414 alkyl thio group Chemical group 0.000 claims description 55
- 125000005110 aryl thio group Chemical group 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 53
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 52
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 113
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 96
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- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 84
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 27
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- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical group CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 18
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- 150000001412 amines Chemical class 0.000 description 12
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 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 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
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- 239000000243 solution Substances 0.000 description 10
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 238000001771 vacuum deposition Methods 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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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 from korean patent application No. 10-2019-0093187, filed in the korean patent office on 31 th 2019, the entire contents of which are incorporated herein.
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 and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, 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. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
In this specification, an organic light emitting device is described.
Solution to the problem
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, wherein the organic layer includes 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-mentioned chemical formula 1,
ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
A1, A2, R1 to R3, Z1 and Z2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
n1 to n3 are each integers of 0 to 3, and when n1 to n3 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other,
p1 is either 0 or 1 and,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
e1 to E3 are identical to or different from one another and are each independently an aromatic hydrocarbon ring,
more than 1 of R4 to R8 are represented by the following chemical formula 1-A or 1-B, or are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups 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, substituents in parentheses of 2 or more are the same 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 or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
ar11 to Ar14 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
L11 is a direct bond, or a substituted or unsubstituted arylene,
p2 is either 0 or 1 and,represents the position where the compound of formula 2 binds,
[ chemical formula 3]
(HAr) a -L21-Ar21-L22-(CN) b
In the above-mentioned chemical formula 3, a compound represented by formula 1,
HAr is a substituted or unsubstituted N-containing heterocyclic group,
l21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted aryl group of 2 to 4 valences, or a substituted or unsubstituted heterocyclic group of 2 to 4 valences,
ar21 is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group having a valence of 2, or-O-,
a and b are each an integer of 1 to 3,
when a is 2 or more, hars are 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, excellent efficiency characteristics, and 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 energy level and the LUMO energy level, so that low driving voltage, high efficiency can be achieved, and 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 organic light emitting devices including stacks of 2 or more.
[ description of the 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: luminescent 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 light emitting 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: cover 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 including both 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 certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present description of the invention, Represents a site of binding to another substituent or binding moiety.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same 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, halogen group, cyano (-CN), nitro, hydroxyl, silyl, boron group, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, aryloxy, arylthio, cycloalkyl, aryl, amine, and heterocyclic group, or with a substituent bonded with 2 or more substituents among the above exemplified substituents, or without any substituent.
In the present specification, the connection of 2 or more substituents means that hydrogen of any substituent is replaced with other substituents. For example, isopropyl group may be linked to phenyl group to form Is a substituent of (a).
In this specification, 3 substituent linkages include not only (substituent 1) to (substituent 2) to (substituent 3) linked continuously but also (substituent 2) and (substituent 3) linked to (substituent 1). For example, 2 phenyl groups and isopropyl groups may be linked to formIs a substituent of (a). The same description applies to the case where 4 or more substituents are linked.
In this specification, "substituted with a or B" includes not only the case of being substituted with a alone or B alone, but also the case of being substituted with a and B.
In this specification, "substituted or unsubstituted" means substituted with 1 or more substituents selected from the group consisting of deuterium, halogen group, cyano (-CN), nitro, hydroxyl, silyl, boron group, alkyl group of 1 to 10 carbon atoms, alkenyl group of 2 to 10 carbon atoms, alkynyl group of 2 to 10 carbon atoms, alkoxy group of 1 to 10 carbon atoms, alkylthio group of 1 to 10 carbon atoms, aryloxy group of 6 to 30 carbon atoms, arylthio group of 6 to 30 carbon atoms, cycloalkyl group of 3 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, amine group, and heterocyclic group of 2 to 30 carbon atoms, or with a substituent formed by joining 2 or more groups selected from the above groups, or without any substituent.
In this specification, "substituted or unsubstituted" means substituted with 1 or more substituents selected from the group consisting of deuterium, halogen group, cyano (-CN), nitro, hydroxyl, silyl, boron group, alkyl group of 1 to 6 carbon atoms, alkenyl group of 2 to 6 carbon atoms, alkynyl group of 2 to 6 carbon atoms, alkoxy group of 1 to 6 carbon atoms, alkylthio group of 1 to 6 carbon atoms, aryloxy group of 6 to 20 carbon atoms, arylthio group of 6 to 20 carbon atoms, cycloalkyl group of 3 to 20 carbon atoms, aryl group of 6 to 20 carbon atoms, amine group, and heterocyclic group of 2 to 20 carbon atoms, or with a substituent formed by joining 2 or more groups selected from the above groups, or without any substituent.
Examples of the above substituents are described below, but are 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 branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. As specific examples of the above alkyl group, there are methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and the like, and the above alkyl group may be straight-chain or branched, and according to one example, propyl group includes n-propyl group and isopropyl group, and butyl group includes n-butyl group, isobutyl group and tert-butyl group.
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 includes not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, spiro ring (spiro) and the like. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like, but not limited thereto.
In the present specification, a cycloolefin (cycloolefin) is a cyclic group having a double bond in a hydrocarbon ring, but not an aromatic ring, 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. Cycloolefins include not only monocyclic groups but also bicyclic groups such as bridgehead, fused rings, spiro rings and the like. Examples of the cycloolefin include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, cyclohexene, and the like.
In the present specification, an alkoxy group is a group having an alkyl group attached to an oxygen atom, an alkylthio group is a group having an alkyl group attached to a sulfur atom, and the above description of an alkyl group can be applied to an alkoxy group and an alkyl group of an alkylthio group.
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 phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl, Examples of the group include, but are not limited to, a fluorenyl group, a fluoranthenyl group, and a triphenylene 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 condensed on the aryl group. For example, tetrahydronaphthyl of the following structure is included in the substituted aryl group. In the following structure, one of the carbons of the benzene ring may be attached at other positions.
In this specification, an aryloxy group is a group having an aryl group attached to an oxygen atom, an arylthio group is a group having an aryl group attached to a sulfur atom, and the above description about an aryl group can be applied to an aryl group of an aryloxy group and an arylthio group. The aryl group of the aryloxy group is the same as exemplified above for the aryl group. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethyl-phenoxy group, a 2,4, 6-trimethylphenoxy group, a p-t-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyloxy group, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthrenyloxy group, a 3-phenanthrenyloxy group, a 9-phenanthrenyloxy group, and the like, and examples of the arylthio group include a phenylthio group (phenylthio group), a 2-methylphenylthio group, a 4-t-butylphenylthio group, and the like, but are not limited thereto.
In the present specification, the silyl group may be represented by-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c May each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group and the like.
In the present specification, the boron group may be represented BY-BY d Y e The chemical formula of (A) is shown in the specification, Y is shown in the specification d And Y e May each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, dimethylboronyl, diethylboronyl, t-butylmethylboronyl, vinylmethylboronyl, propylmethylboronyl, methylphenylboronyl, diphenylboronyl, phenylboronyl, and the like.
In the present specification, the amine group may be represented by-NRaRb, and Ra and Rb described above 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 above amine groups may be selected from alkylamino groups, alkylaryl amine groups, arylamino groups, heteroaryl amine groups, alkylheteroaryl amine groups, and arylheteroaryl amine groups, depending on the kind of substituents (Ra, rb) to be bonded.
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 or 1 to 20. Specific examples of the alkylamino group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, and the like.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamino group, or a substituted or unsubstituted arylheteroarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamino group include a phenylamino group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a diphenylamino group, a phenylnaphthylamino group, a bis (t-butylphenyl) amino group, and the like, but are not limited thereto.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted mono-heteroarylamino group, a substituted or unsubstituted di-heteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group.
In the present specification, an arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group, and the description of the above aryl group and the heteroaryl group described later can be applied.
In the present specification, a heterocyclic group is a ring group containing 1 or more hetero atoms of N, O, S and Si, 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, and dibenzosilazaneHeterocyclylalkyl, phenonesOxazinyl (phenoxazine), phenothiazinyl (phenothiazine), dihydrodibenzosilahexenyl, spiro (dibenzosilole-dibenzosilacyclohexane) group, spiro (acridine-fluorene) group, and the like, but are not limited thereto.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted by the substituent.
In the present specification, the term "ring formed by bonding adjacent groups" means a hydrocarbon ring or a heterocyclic ring.
In this specification, the "five-or six-membered ring formed by bonding adjacent groups" means that the ring containing the substituents involved in ring formation is five-or six-membered. It is possible to include the case where other rings are condensed on the above-mentioned ring containing the substituent participating in ring formation.
In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, the description of the aryl group may be applied to the aromatic hydrocarbon ring except for 1, and the description of the cycloalkyl group may be applied to the aliphatic hydrocarbon ring except for 1. Examples of the condensed rings of the aromatic group and the aliphatic group include, but are not limited to, 1,2,3, 4-tetrahydronaphthyl, 2, 3-dihydro-1H-indenyl, and the like.
In this specification, the heterocyclic ring is not 1-valent, and the description of the heterocyclic group can be applied.
In the present specification, an aromatic hydrocarbon ring means a ring of a plane in which pi electrons are completely conjugated, and the above description of an aryl group can be applied in addition to a 2-valent group.
In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include cycloalkyl rings. The cycloalkyl ring may be a 2-valent group, and the above description of cycloalkyl groups may be applied. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring having an aromatic ring condensed therein.
In this specification, arylene groups other than the 2-valent groups may be used as described above with respect to aryl groups.
In this specification, the cycloalkyl group is not a 2-valent group, and the above description of the cycloalkyl group can be applied.
Next, chemical formula 1 is described.
[ chemical formula 1]
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, ar1 to Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having from 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having from 6 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocyclic group having from 2 to 30 carbon atoms, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having from 5 to 30 carbon atoms.
In another embodiment, ar1 to Ar4 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, ar1 through Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, 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 are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, ar1 to Ar4 are the same 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 substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms which is substituted or unsubstituted by bonding with an adjacent group, and 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 a substituent obtained by bonding 2 or more groups selected from the group, and a monocyclic to bicyclic aliphatic or aromatic hydrocarbon ring may be condensed on the aliphatic hydrocarbon ring.
In another embodiment, ar1 through Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, an alkyl group of 1 to 6 carbon atoms, or an aryl group of 6 to 20 carbon atoms, or are combined with adjacent groups to form a six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, or with a hydrocarbon ring of mono-to bicyclic ring fused or unfused.
In another embodiment, ar1 through Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, an alkyl group of 1 to 6 carbon atoms, or an aryl group of 6 to 20 carbon atoms, or are combined with adjacent groups to form a six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms, which is condensed or unfused with benzene or cyclohexane.
According to another embodiment, ar1 to Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or unsubstituted phenyl, or are combined with adjacent groups to form substituted or unsubstituted cyclohexane, substituted or unsubstituted tetrahydronaphthalene, or substituted or unsubstituted decalin. At this time, the adjacent groups may be 2 selected from Ar1 to Ar 4.
According to another embodiment, ar1 to Ar4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, or phenyl substituted or unsubstituted by deuterium, or combine with an adjacent group to form deuterium substituted or unsubstituted cyclohexane; tetrahydronaphthalene substituted or unsubstituted with deuterium, butyl or phenyl; or deuterium substituted or unsubstituted decalin. At this time, the adjacent groups may be 2 selected from Ar1 to Ar 4.
According to an embodiment of the present specification, 2 adjacent ones of Ar1 to Ar4 form a substituted or unsubstituted aliphatic hydrocarbon ring, and the remaining 2 are the substituents described above.
In this specification, ar1 to Ar4 are bonded to each other to form a ring means that Ar1 and Ar3, or Ar2 and Ar4 are bonded 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 or different from each other, are substituents in which an aliphatic hydrocarbon ring is not formed in Ar1 to Ar4,
Y1 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
y1 is an integer of 0 to 14, and Y1 is the same as or different from each other when Y1 is 2 or more.
According to an 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 having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
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 an embodiment of the present disclosure, Y1 is hydrogen, deuterium, or methyl.
In one embodiment of the present description, 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 description, ar101 and Ar102 are the same or different from each other, and 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 are the same as or different from each other, and 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 are the same or different from each other, and 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 and are each independently hydrogen, deuterium, fluoro, methyl, ethyl, butyl, or phenyl.
In one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 101 or 102.
In the above-mentioned chemical formulas 101 and 102,
a1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are as defined in the above chemical formula 1,
g1 to G4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
G11 is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group 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 are the same or different from each other,
p3 is 0 or 1.
In an embodiment of the present specification, G1 to G4 may be applied to the above description about Ar1 to Ar 4.
In one embodiment of the present specification, G11 may be applied to the description above regarding Y1.
In another embodiment, g11 may apply to the description above with respect to y 1.
In one embodiment of the present description, p3 is 1.
In one embodiment of the present specification, G1 to G4 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, 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 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or unsubstituted phenyl.
According to another embodiment, G1 to G4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, or phenyl substituted or unsubstituted by deuterium.
According to an 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 combined with 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 is combined 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 is combined with an adjacent group to form a substituted or unsubstituted cyclohexane, or a substituted or unsubstituted benzene.
According to another embodiment, G11 is hydrogen, deuterium, methyl, tert-butyl or phenyl, or is combined with an adjacent group to form methyl substituted or unsubstituted cyclohexane, or is combined with an adjacent group to form butyl or phenyl substituted or unsubstituted benzene.
According to an embodiment of the present disclosure, G11 is hydrogen, deuterium, or methyl.
In one embodiment of the present specification, A1 and A2 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted amino, or substituted or unsubstituted heterocyclyl, or is combined with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, A1 and A2 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having from 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having from 6 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group having from 2 to 30 carbon atoms, or a substituted or unsubstituted ring having from 5 to 30 carbon atoms combined with an adjacent group.
In another embodiment, A1 and A2 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or are combined with each other to form a substituted or unsubstituted ring.
According to another embodiment, A1 and A2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, 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 are combined with each other to form a substituted or unsubstituted five-or six-membered ring.
According to another embodiment, A1 and A2 are identical to or different from each other and 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 are combined with each other to form a five-or six-membered ring,
the aryl group, heterocyclic group or ring of the above-mentioned A1 and A2 is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, halogen group, alkyl group having 1 to 10 carbon atoms, silyl group and aryl group having 6 to 30 carbon atoms, or substituents formed by joining 2 or more groups selected from the above-mentioned groups, or a five-membered or six-membered hydrocarbon ring substituted or unsubstituted with the above-mentioned substituents is condensed or unfused.
According to another embodiment, A1 and A2 are identical to or different from each other and 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 are combined with each other to form a five-or six-membered ring,
The aryl group, heterocyclic group or ring of the above-mentioned A1 and A2 is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, halogen group, alkyl group having 1 to 6 carbon atoms, silyl group and aryl group having 6 to 20 carbon atoms, or substituents formed by joining 2 or more groups selected from the above-mentioned groups, or a five-membered or six-membered hydrocarbon ring substituted or unsubstituted with the above-mentioned substituents is condensed or unfused.
In one embodiment of the present description, A1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or is combined with A2 to form a substituted or unsubstituted ring.
In one embodiment of the present description, A2 is hydrogen or deuterium, or is combined with A1 or R1 to form a substituted or unsubstituted ring.
In another embodiment, A2 is hydrogen or deuterium, or is combined with A1 to form a substituted or unsubstituted five-or six-membered ring, or is combined 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 above chemical formula 1 is represented by any one of the following chemical formulas 103 to 106.
In the above-mentioned chemical formulas 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 to G8 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
z3, Z4, G12 and G13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined 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 each of g12 and g13 is 2 or more, substituents in brackets of 2 or more are the same or different from each other,
p4 and p5 are each 0 or 1.
In an embodiment of the present specification, A3 may be applied to the description of A1 described above. In another embodiment, A4 may apply to the description above with respect to A2.
In one embodiment of the present description, p4 is the same as p 1.
In one embodiment of the present description, 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 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 formed by joining 2 or more groups selected from the above groups, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is condensed or unfused.
In another embodiment, the aryl 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 formed by joining 2 or more groups selected from the above groups, or a five-or six-membered hydrocarbon ring substituted or unsubstituted with the above substituents is condensed or unfused.
In another embodiment, A3 is 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, 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 joining 2 or more groups selected from the group, and which is condensed or not condensed with a five-or six-membered aliphatic hydrocarbon ring; 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, 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 groups selected from the group.
In another embodiment, A3 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted tetrahydronaphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.
In another embodiment, A3 is phenyl substituted or unsubstituted with deuterium, fluoro, methyl, ethyl, propyl, butyl, 2-phenylpropane-2-yl (2-phenylpropan-2-yl), ph-d5, naphthyl or tetramethyltetralin; biphenyl substituted or unsubstituted with deuterium, methyl, ethyl, propyl, butyl, trimethylsilyl, 2-phenylpropane-2-yl; terphenyl substituted or unsubstituted with deuterium or butyl; a naphthyl group substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted with deuterium, methyl or phenyl; a fluorenyl group 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 description, A4 is hydrogen or deuterium, or is combined with R1 to form a substituted or unsubstituted ring.
In another embodiment, A2 is hydrogen or deuterium, or is combined with R1 to form a substituted or unsubstituted five-or six-membered ring.
In another embodiment, A2 is hydrogen or deuterium, or is combined 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 an embodiment of the present specification, G5 to G8 may be applied to the above description about G1 to G4. In another embodiment, G12 and G13 may apply to the description above with respect to G11.
In one embodiment of the present specification, G5 to G8 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to another embodiment, G5 to G8 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or unsubstituted phenyl.
According to another embodiment, G5 to G8 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, or phenyl substituted or unsubstituted by deuterium.
According to an embodiment of the present specification, G12 and G13 are the same or different from each other, and are 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 a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms, which is bonded to an adjacent group.
According to another embodiment, G12 and G13 are the same or different from each other and 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 are combined 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 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted trimethylsilyl, or substituted or unsubstituted phenyl, or are combined with adjacent groups to form substituted or unsubstituted cyclohexane, or substituted or unsubstituted benzene.
According to another embodiment, G12 is combined with an adjacent G12 to form a substituted or unsubstituted ring.
According to another embodiment, G13 is combined with an adjacent G13 to form a substituted or unsubstituted ring.
According to another embodiment, G12 is hydrogen, deuterium, or methyl, or is combined with adjacent G12 to form cyclohexane.
In another embodiment, G13 is hydrogen, deuterium, methyl, trimethylsilyl, or phenyl, or is combined with an adjacent G13 to form phenyl substituted or unsubstituted benzene.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
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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 or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
z1 to Z4 and Ar21 to Ar24 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring.
In this specification, the adjacent groups in Ar21 to Ar24 are bonded to each other to form a ring means that i) 2 of Ar21 to Ar24 are bonded to each other to form an aliphatic hydrocarbon ring, or ii) Ar21 to Ar24 each participate in ring formation to form an aromatic hydrocarbon ring.
In one embodiment of the present specification, ar21 to Ar24 may be as described above with respect to the substituents G5 to G8, the aliphatic hydrocarbon ring to which G11 is attached, and the aromatic hydrocarbon ring to which G12 is attached.
In one embodiment of the present specification, ar21 to Ar24 are the same as or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or are combined with an adjacent group to form a substituted or unsubstituted hydrocarbon ring.
In another embodiment, ar21 through Ar24 are the same as or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, 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 are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.
In another embodiment, ar21 through Ar24 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or are combined with adjacent groups to form a six-membered hydrocarbon ring substituted or unsubstituted with deuterium, an alkyl group of 1 to 6 carbon atoms, an alkylsilyl group of 1 to 18 carbon atoms, or an arylsilyl group of 6 to 60 carbon atoms, which is fused or unfused with a monocyclic to bicyclic hydrocarbon ring.
In another embodiment, ar21 through Ar24 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, deuterium-substituted or unsubstituted alkyl of 1 to 6 carbon atoms, or deuterium-substituted or unsubstituted aryl of 6 to 20 carbon atoms, or are combined with adjacent groups to form a six-membered hydrocarbon ring substituted or unsubstituted with deuterium, alkyl of 1 to 6 carbon atoms, alkylsilyl of 1 to 18 carbon atoms, or arylsilyl of 6 to 60 carbon atoms, fused or unfused with cyclohexane or benzene.
According to another embodiment, ar21 to Ar24 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, or substituted or unsubstituted phenyl, or are combined with adjacent groups to form substituted or unsubstituted cyclohexane, substituted or unsubstituted benzene, or 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 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, cyano, methyl, ethyl or phenyl, or combine with an adjacent group to form cyclohexane; decalin; 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 or different from each other, are substituents which do not form an aliphatic hydrocarbon ring in Ar21 to Ar24,
y2 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
y2 is an integer of 0 to 14, and Y2 is the same as or different from each other when Y2 is 2 or more.
In one embodiment of the present description, 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 an embodiment of the present specification, ar103 and Ar104 are the same or different from each other, and 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 are the same or different from each other and 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 are the same or different from each other and 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 and are each independently hydrogen, deuterium, fluoro, methyl, ethyl, butyl, or phenyl.
According to an 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 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.
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, substituted or unsubstituted methyl, substituted or unsubstituted trimethylsilyl, or substituted or unsubstituted phenyl.
According to an embodiment of the present disclosure, Y2 is hydrogen, deuterium, or methyl.
According to an embodiment of the present specification, R1 to R3 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having from 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having from 6 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group having from 2 to 30 carbon atoms, or are combined with an adjacent group to form a substituted or unsubstituted ring having from 3 to 30 carbon atoms.
In another embodiment, R1 to R3 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, cyano, 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 are combined with adjacent groups to form a substituted or unsubstituted ring.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 90 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are combined with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 60 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, a substituted or unsubstituted arylamine group of 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group of 2 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group of 2 to 20 carbon atoms, or are combined with an adjacent group to form a substituted or unsubstituted ring of 2 to 20 carbon atoms.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkylsilyl group of 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 60 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, NY11Y12, or a substituted or unsubstituted heterocyclic group of 2 to 20 carbon atoms, or are combined with an adjacent group to form a substituted or unsubstituted ring of 2 to 20 carbon atoms.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; an alkylaryl silyl group having 7 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 10 carbon atoms, silyl and aryl of 6 to 30 carbon atoms, or with 2 or more groups selected from the group; NY11Y12; 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 a substituent formed by joining 2 or more groups 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 a substituent formed by joining 2 or more groups selected from the above group, by bonding adjacent groups.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; a deuterium-substituted or unsubstituted alkylaryl silyl group having 7 to 40 carbon atoms; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 20 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 6 carbon atoms, silyl and aryl of 6 to 20 carbon atoms, or with 2 or more groups selected from the group; NY11Y12; 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 a substituent formed by joining 2 or more groups 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 a substituent formed by joining 2 or more groups selected from the above group, by bonding adjacent groups.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, NY11Y12, substituted or unsubstituted N-containing heterocyclyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or are combined with adjacent groups to form a substituted or unsubstituted benzofuran, substituted or unsubstituted ring.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted bisphenylamino, substituted or unsubstituted phenyldibenzofuranamino, substituted or unsubstituted phenyldibenzothiophenamino, substituted or unsubstituted N-containing heterocyclyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or are combined with adjacent groups to form a substituted or unsubstituted benzofurane, substituted or unsubstituted thiophene, substituted or unsubstituted indole, substituted or unsubstituted indene, substituted or unsubstituted cyclopentene, or substituted or unsubstituted cyclopentene.
In another embodiment, R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted bisphenylamino, substituted or unsubstituted phenyldibenzofuranamino, substituted or unsubstituted phenyldibenzothiophenamino, substituted or unsubstituted carbazolyl, substituted or unsubstituted hexahydrocarbazolyl, substituted or unsubstituted dihydroacridinyl, substituted or unsubstituted phenoneAn oxazinyl (phenoxazine), a substituted or unsubstituted phenothiazinyl (phenothiazine), a substituted or unsubstituted dihydrodibenzoazacyclohexanyl, a substituted or unsubstituted spiro (dibenzosilole-dibenzoazacyclohexanyl), a substituted or unsubstituted spiro (acridine-fluorene), a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothienyl, or is combined with adjacent groups 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 are identical to or different from each other and 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 substituted or unsubstituted with deuterium, fluoro, methyl, trifluoromethyl, trimethylsilyl or naphthyl; a naphthyl group substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD 3 Tert-butyl, 2-phenylpropane-2-yl, trimethylsilyl, triphenylsilyl or phenyl-substituted or unsubstituted diphenylamino groups, fused or unfused with hexene; phenyl naphthylamine group substituted or unsubstituted with deuterium or tert-butyl; phenylbiphenylamine groups substituted or unsubstituted with deuterium or tert-butyl; a bis-biphenylamino group substituted or unsubstituted with deuterium or tert-butyl; phenyl dibenzofuran amine group substituted or unsubstituted with deuterium, methyl or tert-butyl, fused or unfused with hexene; phenyl dibenzothiophene amine groups substituted or unsubstituted with deuterium, methyl or tert-butyl, fused or unfused with hexene; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; hexahydrocarbazolyl substituted or unsubstituted by deuterium, fluoro, cyano, methyl, phenyl or Ph-d5, fused or unfused with hexane, hexene or benzene; a dihydroacridinyl group substituted or unsubstituted with methyl, ethyl or phenyl; phenones An oxazinyl group; a phenothiazinyl group; a dihydrodibenzosilacyclohexyl substituted or unsubstituted with phenyl; a spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzosilol-dibenzoazacyclohexane) yl; dibenzofuranyl; or dibenzothienyl.
According to another embodiment, R1 to R3 combine with adjacent groups to form a benzofuran, naphthobenzofuran, thiophene, indole, indene, spiro (fluorene-indene), cyclopentene, or cyclohexene substituted or unsubstituted with tert-butyl or phenyl, substituted or unsubstituted with tert-butyl, substituted or unsubstituted with methyl or tert-butyl.
According to another embodiment, 2 adjacent R1, R1 and A2, R1 and A4, or 2 adjacent R2 are combined with adjacent groups to form a benzofuran, naphthobenzofuran, thiophene, indole, indene, spiro (fluorene-indene), cyclopentene, or cyclohexene substituted or unsubstituted with tert-butyl or phenyl, methyl or tert-butyl.
In another embodiment, the N-containing heterocyclic group of the above R1 to R3 may be represented by any one of the following formulas HAr1 to HAr3 or formula 1-B.
In the above formulas HAr1 to HAr3,
q1 is CY4Y5 or SiY4Y5, Q2 is C or Si,
y3 to Y5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
y3 is an integer of 0 to 8, and when Y3 is 2 or more, 2 or more Y3 are the same or different from each other.
According to an embodiment of the present specification, Y3 to Y5 are the same or different from each other, and 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.
According to another embodiment, Y3 to Y5 are the same or different from each other and 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 are the same or different from each other and are each independently hydrogen, deuterium-substituted or unsubstituted methyl, deuterium-substituted or unsubstituted ethyl, deuterium-substituted or unsubstituted butyl, or deuterium-substituted or unsubstituted phenyl.
According to another embodiment, Y3 to Y5 are identical to or different from each other and 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 are identical to or different from each other and are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl or phenyl.
In one embodiment of the present specification, Y11 and Y12 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12 are the same or different from each other and are each independently 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 condensed ring group having 9 to 30 carbon atoms of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12 are the same or different from each other and are each independently 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 condensed ring group having 9 to 20 carbon atoms of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
In another embodiment, Y11 and Y12 are the same or different from each other, and each is 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 formed by joining 2 or more groups selected from the above group; 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 groups selected from the group consisting of the above groups; or a condensed ring group having 9 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 a substituent formed by joining 2 or more groups selected from the above groups.
In another embodiment, Y11 and Y12 are the same or different from each other and each is independently an aryl group having 6 to 20 carbon atoms 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 joining 2 or more groups selected from the above group; 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 groups selected from the group consisting of the above groups; or a condensed ring group having 9 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 a substituent formed by joining 2 or more groups selected from the above groups.
In another embodiment, Y11 and Y12 are the same or different from each other and are each independently aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group of 1 to 10 carbon atoms, an arylalkyl group of 7 to 60 carbon atoms, an alkylsilyl group of 1 to 30 carbon atoms, or an arylsilyl group of 6 to 90 carbon atoms; a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms; or a condensed ring group of 9 to 30 carbon atoms of 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 are the same or different from each other and are each independently aryl groups of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group of 1 to 6 carbon atoms, an arylalkyl group of 7 to 40 carbon atoms, an alkylsilyl group of 1 to 18 carbon atoms, or an arylsilyl group of 6 to 60 carbon atoms; 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 of 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 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted tetrahydronaphthyl group.
In another embodiment, Y11 and Y12 are the same or different from each other and are each independently phenyl substituted or unsubstituted with deuterium, a halogen group, cyano, alkyl of 1 to 6 carbon atoms, arylalkyl of 7 to 40 carbon atoms, alkylsilyl of 1 to 18 carbon atoms, or arylsilyl of 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; a naphthyl 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; dibenzofuranyl 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 with deuterium or an alkyl group having 1 to 6 carbon atoms.
In another embodiment, Y11 and Y12 are the same or different from each other and are each independently deuterium, fluoro, cyano, methyl, CD 3 A phenyl group substituted or unsubstituted with butyl, trimethylsilyl, triphenylsilyl, or 2-phenylpropane-2-yl; biphenyl substituted or unsubstituted with deuterium; a naphthyl group 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 with deuterium or methyl.
In one embodiment of the present specification, R1 to R3 are combined with adjacent groups to form a ring represented by Cy11 or Cy12 described below. Specifically, 2 adjacent R1, R1 and A2, R1 and A4, or 2 adjacent R2 are bonded to each other to form a ring represented by the following chemical formula Cy11 or Cy 12.
[ formula Cy11] [ formula Cy12]
In the above formulas Cy11 and Cy12,
the double dashed line is the fused position,
q3 is O, S, NY, CY10Y11 or SiY10Y11,
y7 to Y11 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,
p10 is either 1 or 2 and,
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, substituents in brackets of 2 or more are the same 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 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 are combined with adjacent groups to form a ring having 3 to 30 carbon atoms.
According to another embodiment, Y7 to Y11 are identical to or different from each other and 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 are combined with adjacent groups to form a ring having 3 to 20 carbon atoms.
According to another embodiment, Y7 to Y11 are the same or different from each other and are each independently hydrogen, deuterium-substituted or unsubstituted methyl, deuterium-substituted or unsubstituted ethyl, deuterium-substituted or unsubstituted butyl, or deuterium-substituted or unsubstituted phenyl, or are combined with adjacent groups to form deuterium-substituted or unsubstituted hexane, deuterium-substituted or unsubstituted hexene, or deuterium-substituted or unsubstituted benzene.
According to another embodiment, Y7 to Y11 are identical to or different from each other and 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 is combined 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 is combined 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 or different from each other, each is independently methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium or butyl, or Y10 and Y11 are each phenyl 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 or different from each other, each is independently methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium or butyl, or Y10 and Y11 are each phenyl substituted or unsubstituted with deuterium or butyl, and combine with each other to form dibenzosilole substituted or unsubstituted with deuterium or butyl.
In one embodiment of the present description, 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 disclosure, 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 groups substituted or unsubstituted with deuterium.
In one embodiment of the present specification, 2 adjacent R1, R1 and A2, R1 and A4, or 2 adjacent R2 are bonded to each other to form a ring represented by the above chemical formula Cy 11.
In another embodiment, 2 adjacent R1 or 2 adjacent R2 are bonded to each other to form a ring represented by the above formula Cy 12.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, 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 substituted or unsubstituted with deuterium, fluoro, methyl, trifluoromethyl, trimethylsilyl or naphthyl; a naphthyl group substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl Base, CD 3 Tert-butyl, 2-phenylpropane-2-yl, trimethylsilyl, triphenylsilyl or phenyl-substituted or unsubstituted diphenylamino groups, fused or unfused with hexene; phenyl naphthylamine group substituted or unsubstituted with deuterium or tert-butyl; phenylbiphenylamine groups substituted or unsubstituted with deuterium or tert-butyl; a bis-biphenylamino group substituted or unsubstituted with deuterium or tert-butyl; phenyl dibenzofuran amine group substituted or unsubstituted with deuterium, methyl or tert-butyl, fused or unfused with hexene; phenyl dibenzothiophene amine groups substituted or unsubstituted with deuterium, methyl or tert-butyl, fused or unfused with hexene; hexahydrocarbazolyl substituted or unsubstituted by deuterium, fluoro, cyano, methyl, phenyl or Ph-d5, or with hexane, hexene or benzene, or with adjacent groups to form tert-butyl-or phenyl-substituted or unsubstituted benzofuran, naphthobenzofuran, tert-butyl-substituted or unsubstituted thiophene, phenyl-substituted or unsubstituted indole, methyl-or tert-butyl-substituted or unsubstituted indene, tert-butyl-substituted or unsubstituted spiro (fluorene-indene), methyl-substituted or unsubstituted cyclopentene, or methyl-substituted or unsubstituted cyclohexene.
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 substituted or unsubstituted with deuterium, fluoro, methyl, trifluoromethyl, trimethylsilyl or naphthyl; a naphthyl group substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD 3 Tert-butyl, 2-phenylpropane-2-yl, trimethylsilyl, triphenylsilyl or phenyl-substituted or unsubstituted diphenylamino groups, fused or unfused with hexene; phenyl naphthylamine group substituted or unsubstituted with deuterium or tert-butyl; phenylbiphenylamine groups substituted or unsubstituted with deuterium or tert-butyl; a bis-biphenylamino group substituted or unsubstituted with deuterium or tert-butyl; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; hexahydrocarbazolyl substituted or unsubstituted by deuterium, fluoro, cyano, methyl, phenyl or Ph-d5, fused or unfused with hexane, hexene or benzene; by methyl or ethyl groupsOr phenyl substituted or unsubstituted dihydroacridinyl; phenonesAn oxazinyl group; a phenothiazinyl group; a dihydrodibenzosilacyclohexyl substituted or unsubstituted with phenyl; a spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzosilol-dibenzoazacyclohexane) yl; dibenzofuranyl; or dibenzothienyl.
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 one embodiment of the present description, p1 is 0 or 1.
In one embodiment of the present specification, Z1 to Z4 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.
In another embodiment, Z1 to Z4 are the same or different from each other and 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 to Z4 are the same or different from each other and 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 to Z4 are the same or different from each other, 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.
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Next, chemical formula 2 is described.
[ chemical formula 2]
According to an embodiment of the present specification, E1 to E3 are the same or different from each other, and each is independently an aromatic hydrocarbon ring.
According to another embodiment, E1 to E3 are identical to or different from each other and are each independently benzene or naphthalene.
According to another embodiment, E1 and E2 are identical to or different from each other and 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 adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others are the same or different from each other, each being independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups 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 or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
ar11 to Ar14 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
L11 is a direct bond, or a substituted or unsubstituted arylene,
p2 is either 0 or 1 and,the position of the bond with chemical formula 2 is shown.
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 or different from each other, each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 10 carbon atoms, and are combined with an adjacent group 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 are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups 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 are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others are the same or different from each other, each being independently hydrogen, deuterium, a halogen group, cyano, 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, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted dihydroacridinyl group.
In an embodiment of the present specification, 1 or more of i) R4 to R8 are represented by the above chemical formula 1-a or 1-B, or ii) 2 adjacent R4 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or iii) 2 adjacent R5 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or iv) 2 adjacent R6 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or v) 2 adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or vi) 2 adjacent R8 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, 1 or more of i) 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 an alkyl-substituted or unsubstituted five-or six-membered aliphatic hydrocarbon ring, or iii) adjacent 2R 5 are bonded to each other to form an alkyl-substituted or unsubstituted five-or six-membered aliphatic hydrocarbon ring, or iv) adjacent 2R 6 are bonded to each other to form an alkyl-substituted or unsubstituted five-or six-membered aliphatic hydrocarbon ring, or v) adjacent 2R 7 are bonded to each other to form an alkyl-substituted or unsubstituted five-or six-membered aliphatic hydrocarbon ring, or vi) adjacent 2R 8 are bonded to each other to form an alkyl-substituted or unsubstituted five-or six-membered aliphatic hydrocarbon ring. In this case, the aliphatic hydrocarbon ring of ii) to vi) may contain 1 or more alkyl groups as substituents, or may contain substituents other than alkyl groups.
In another embodiment, 1 or more of i) R4 to R8 are represented by the above chemical formula 1-a or 1-B, or ii) 2 adjacent R4 are bonded to each other to form methyl-substituted or unsubstituted pentene, or methyl-substituted or unsubstituted hexene, or iii) 2 adjacent R5 are bonded to each other to form methyl-substituted or unsubstituted pentene, or methyl-substituted or unsubstituted hexene, or iv) 2 adjacent R6 are bonded to each other to form methyl-substituted or unsubstituted pentene, or methyl-substituted or unsubstituted hexene, or v) 2 adjacent R7 are bonded to each other to form methyl-substituted or unsubstituted pentene, or methyl-substituted or unsubstituted hexene, or vi) 2 adjacent R8 are bonded to each other to form methyl-substituted or unsubstituted pentene, or methyl-substituted or unsubstituted hexene. In this case, the methyl group may be substituted with deuterium.
The compound of the above chemical formula 2 may correspond to not only one of the above i) to vi), but also 2 or more of the above i) to vi). That is, the compound of the above compound 2 may correspond to the above i) or ii).
In an embodiment of the present specification, 1 or more of R4 to R8 are represented by the above chemical formula 1-a or 1-B, or the remaining substituents which are not combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring (hereinafter referred to as "remaining substituents in R4 to R8") are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.
In another embodiment, the remaining substituents of R4 to R8 may be as described above with respect to R1 to R3 of chemical formula 1.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl of from 1 to 10 carbon atoms, substituted or unsubstituted alkenyl of from 2 to 10 carbon atoms, substituted or unsubstituted alkynyl of from 2 to 10 carbon atoms, substituted or unsubstituted alkoxy of from 1 to 10 carbon atoms, substituted or unsubstituted alkylthio of from 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl of from 3 to 30 carbon atoms, substituted or unsubstituted aryl of from 6 to 30 carbon atoms, substituted or unsubstituted aryloxy of from 6 to 30 carbon atoms, substituted or unsubstituted amino of from 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclyl of from 2 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring of from 3 to 30 carbon atoms.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each being independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, or substituted or unsubstituted heterocyclyl, or combined with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 90 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group of 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group of 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamino group of 2 to 90 carbon atoms, or a substituted or unsubstituted heterocyclyl group of 2 to 30 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted ring of 2 to 30 carbon atoms.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted alkylsilyl group of 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 60 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, a substituted or unsubstituted alkylamino group of 1 to 18 carbon atoms, a substituted or unsubstituted arylamino group of 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamino group of 2 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group of 2 to 20 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted ring of 2 to 20 carbon atoms.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted alkylsilyl group of 1 to 18 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 60 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, a substituted or unsubstituted alkylamino group of 1 to 18 carbon atoms, NY11Y12, or a substituted or unsubstituted heterocyclyl group of 2 to 20 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted ring of 2 to 20 carbon atoms.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; an alkylaryl silyl group having 7 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 10 carbon atoms, silyl and aryl of 6 to 30 carbon atoms, or with 2 or more groups selected from the group; an alkylamino group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; NY11Y12; 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 a substituent formed by joining 2 or more groups 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 a substituent formed by joining 2 or more groups selected from the above group, by bonding adjacent groups.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; a deuterium-substituted or unsubstituted alkylaryl silyl group having 7 to 40 carbon atoms; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 20 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 6 carbon atoms, silyl and aryl of 6 to 20 carbon atoms, or with 2 or more groups selected from the group; a substituted or unsubstituted alkylamino group having 1 to 18 carbon atoms; NY11Y12; 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 a substituent formed by joining 2 or more groups 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 a substituent formed by joining 2 or more groups selected from the above group, by bonding adjacent groups.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dimethylamino, NY11Y12, substituted or unsubstituted N-containing heterocyclyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or is combined with an adjacent group to form a substituted or unsubstituted benzofuran, substituted or unsubstituted ring.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted bisbiphenylamino, substituted or unsubstituted phenyldibenzofuranamino, substituted or unsubstituted phenyldibenzothiophenamino, substituted or unsubstituted N-containing heterocyclyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination with an adjacent group to form a substituted or unsubstituted benzofuran, substituted or unsubstituted indene, substituted or unsubstituted cyclohexene, or unsubstituted cyclohexene.
In another embodiment, the remaining substituents in R4 to R8 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted carbazolyl, substituted or unsubstituted dihydroacridinyl, substituted or unsubstituted phenoneAn oxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted dihydrodibenzosilahexenyl group, a substituted or unsubstituted spiro (dibenzosilole-dibenzosilahexenyl) group, a substituted or unsubstituted spiro (acridine-fluorene) group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, or a combination 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 are the same or different from each other, each independently hydrogen; deuterium; a fluorine group; methyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with deuterium; quilt is covered withDeuterium substituted or unsubstituted tert-butyl; trimethylsilyl substituted or unsubstituted with deuterium; phenyl substituted or unsubstituted with deuterium, fluoro, cyano, methyl, trifluoromethyl, trimethylsilyl, butyldimethylsilyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluoro or tert-butyl; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium, methyl; a dimethylamino group substituted or unsubstituted with deuterium; by deuterium, fluoro, cyano, methyl, CD 3 Tert-butyl, 2-phenylpropane-2-yl, trimethylsilyl, triphenylsilyl or phenyl-substituted or unsubstituted diphenylamino groups, fused or unfused with hexene; phenyl naphthylamine group substituted or unsubstituted with deuterium or tert-butyl; phenylbiphenylamine groups substituted or unsubstituted with deuterium or tert-butyl; carbazolyl substituted or unsubstituted with deuterium or tert-butyl; a dihydroacridinyl group substituted or unsubstituted with methyl, ethyl or phenyl; phenones An oxazinyl group; a phenothiazinyl group; a dihydrodibenzosilacyclohexyl substituted or unsubstituted with phenyl; a spiro (acridine-fluorene) group substituted or unsubstituted with methyl; spiro (dibenzosilol-dibenzoazacyclohexane) yl; dibenzofuranyl; or dibenzothienyl.
According to another embodiment, the remaining substituents of R4 to R8 combine with adjacent groups to form a benzofuran, naphthobenzofuran, thiophene, indole, indene, spiro (fluorene-indene), cyclopentene, or cyclohexene substituted or unsubstituted with tert-butyl or phenyl, substituted or unsubstituted with methyl or tert-butyl, substituted or unsubstituted with tert-butyl.
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 a benzofuran, naphthobenzofuran, thiophene substituted or unsubstituted with tert-butyl or phenyl, 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 groups of R4 to R8 may be represented by any one of the above chemical formulas HAr1 to HAr3, or the above chemical formula 1-B.
In one embodiment of the present specification, the remaining substituents of R4 to R8 are bonded to 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, 2 adjacent R7 or 2 adjacent R8 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 formula Cy 12.
In one embodiment of the present specification, the above chemical formula 2 is represented by any one of the following chemical formulas 201 to 203.
[ chemical formula 203]
In the above-mentioned chemical formulas 201 to 203,
e1 to E3, n4 to n8 are as defined in chemical formula 2,
r4 to R8, R11 and R12 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
p6 and p7 are each 1 or 2,
n5 'is an integer from 0 to 2, n 8' is an integer from 0 to 3, n11 and n12 are each an integer from 0 to 8,
when n5", n8", n11 and n12 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other.
In an embodiment of the present specification, R11 and R12 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 are combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, R11 and R12 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or are combined 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 are the same or different from each other and 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 are combined with adjacent groups 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 are the same or different from each other and are each independently hydrogen, deuterium, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or are combined with adjacent groups to form an aromatic hydrocarbon ring of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring of 3 to 20 carbon atoms substituted or unsubstituted with deuterium.
In another embodiment, R11 and R12 are the same or different from each other and are each independently hydrogen, deuterium-substituted or unsubstituted methyl, or deuterium-substituted or unsubstituted phenyl, or combine with adjacent groups to form a phenyl ring substituted or unsubstituted with deuterium or butyl, or combine with adjacent groups to form an indene ring substituted or unsubstituted with deuterium, methyl, or butyl, or combine with adjacent groups to form a spiro (fluorene-indene) substituted or unsubstituted with deuterium, methyl, or butyl.
In another embodiment, R11 and R12 are the same or different from each other and 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 above chemical formula 2 is represented by any one of the following chemical formulas 211 to 219.
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[ chemical formula 219]
In the above-mentioned chemical formulas 211 to 219,
n4 to n8 are defined as in chemical formula 2,
r4 to R8 and R11 to R14 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
p6 to p9 are each 1 or 2,
n4 "and n5" are each integers from 0 to 2, n7 "and n8" are integers from 0 to 3, n11 to n14 are each integers from 0 to 8,
when n4", n5", n7", n8" and n11 to n14 are each 2 or more, substituents in 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 formulas 211 to 219 are hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R13 may be as described above with respect to R11. In another embodiment, R14 may be as described above with respect to R12.
In another embodiment, R13 and R14 are the same or different from each other and are each independently hydrogen, deuterium, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or are combined with adjacent groups to form an aromatic hydrocarbon ring of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring of 3 to 20 carbon atoms substituted or unsubstituted with deuterium.
In another embodiment, R13 and R14 are the same or different from each other and are each independently hydrogen, deuterium-substituted or unsubstituted methyl, or deuterium-substituted or unsubstituted phenyl, or combine with adjacent groups to form a phenyl ring substituted or unsubstituted with deuterium or butyl, or combine with adjacent groups to form an indene ring substituted or unsubstituted with deuterium, methyl, or butyl, or combine with adjacent groups 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,
more than 1 of the aliphatic hydrocarbon rings is represented by any one of the following chemical formulas Cy1 to Cy 3.
In the above formulas Cy1 to Cy3,
r31 to R40 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
r41 to R43 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined 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, substituents in parentheses of 2 or more are the same or different from each other.
In the present specification, the aliphatic hydrocarbon ring included in chemical formula 2 refers to one or more rings among 1) an aliphatic hydrocarbon ring formed by bonding 2R 4 to each other, 2) an aliphatic hydrocarbon ring formed by bonding 2R 5 to each other, 3) an aliphatic hydrocarbon ring formed by bonding 2R 6 to each other, 4) an aliphatic hydrocarbon ring formed by bonding 2R 7 to each other, and 5) an aliphatic hydrocarbon ring formed by bonding 2R 8 to each other.
In one embodiment of the present specification, R31 to R40 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
In another embodiment, R31 to R40 are the same or different from each other, and 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 groups.
In another embodiment, R41 to R43 are the same as or different from each other, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or are combined with adjacent groups to form a substituted or unsubstituted ring.
In another embodiment, R41 to R43 are the same as or different from each other, 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 are combined with adjacent groups to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.
In another embodiment, R41 and R42 are the same or different from each other, each independently hydrogen or deuterium.
In another embodiment, R43 is hydrogen or deuterium, or adjacent 4R 43 are combined 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 groups.
In another embodiment, R43 is hydrogen or deuterium, or adjacent 4R 43 are bonded to each other to form a benzene ring.
In another embodiment, all 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 contained in the 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 formed by bonding 2R 4 to each other, 2) an aliphatic hydrocarbon ring formed by bonding 2R 5 to each other, 3) an aliphatic hydrocarbon ring formed by bonding 2R 6 to each other, 4) an aliphatic hydrocarbon ring formed by bonding 2R 7 to each other, and 5) an aliphatic hydrocarbon ring formed by bonding 2R 8 to each other are selected from the above structures.
In one embodiment of the present specification, the above chemical formula 2 is represented by the following chemical formula 204.
[ chemical formula 204]
In the above-described chemical formula 204,
more than 1 of R21 to R25 are represented by the chemical formula 1-A or 1-B, and the others are the same or different and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted ring,
The definitions of E1 to E3, n4 to n8, and chemical formulas 1-A and 1-B are the same as those in chemical formula 2 described above.
In an embodiment of the present specification, T1 to T11 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted ring.
According to another embodiment, T1 to T11 are identical to or different from each other, are each independently hydrogen or deuterium, or combine with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring.
According to another embodiment, T1 to T11 are identical to or different from each other, each independently hydrogen or deuterium, or are combined with adjacent groups to form a substituted or unsubstituted bridgehead or fused ring aliphatic hydrocarbon ring.
According to another embodiment, T1 to T11 are the same or different from each other and are each independently hydrogen or deuterium, or T1, T4 and T8 are combined with each other to form a substituted or unsubstituted bridgehead or condensed ring aliphatic hydrocarbon ring, or T2, T6 and T10 are combined with each other to form a substituted or unsubstituted bridgehead or condensed ring aliphatic hydrocarbon ring.
In one embodiment of the present description, L11 is a directly bonded, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In another embodiment, L11 is a directly bonded, or substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
In another embodiment, L11 is an arylene group of 6 to 20 carbon atoms directly bonded, or substituted or unsubstituted with an alkyl group of 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 a direct bond, or a phenylene group substituted or unsubstituted with deuterium or tert-butyl.
In one embodiment of the present specification, the above 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 above 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 1-B 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, the definitions of T12 to T17 and p2 are the same as those in the above chemical formula 1-B,
t18 to T21 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
t22 is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is bonded to each other with an adjacent group to form a substituted or unsubstituted ring,
T22 is an integer of 0 to 8, and when T22 is 2 or more, 2 or more T22 s are the same 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 or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms.
In an embodiment of the present specification, T12 to T17 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted ring.
In another embodiment, T12 to T17 are the same or different from each other and 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 are combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.
In another embodiment, T12 to T17 are the same or different from each other and 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 are combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.
In another embodiment, T12 to T17 are the same or different from each other, each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; an alkylaryl silyl group having 7 to 60 carbon atoms which is substituted or unsubstituted with deuterium; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 60 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 10 carbon atoms, silyl and aryl of 6 to 30 carbon atoms, or with 2 or more groups selected from the group; 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 substituents obtained by linking 2 or more groups selected from the group.
In another embodiment, T12 to T17 are the same or different from each other, each independently hydrogen; deuterium; a halogen group; cyano group; an alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; a deuterium-substituted or unsubstituted alkylaryl silyl group having 7 to 40 carbon atoms; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; arylalkyl of 7 to 40 carbon atoms substituted or unsubstituted with deuterium; aryl of 6 to 20 carbon atoms substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, cyano, alkyl of 1 to 6 carbon atoms, silyl and aryl of 6 to 20 carbon atoms, or with 2 or more groups selected from the group; 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 substituents obtained by linking 2 or more groups selected from the group.
In another embodiment, T12 to T15 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted methylsilyl, substituted or unsubstituted butylsilyl, substituted or unsubstituted phenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, or are combined with an adjacent group to form a substituted or unsubstituted hexene, or substituted or unsubstituted benzene.
In another embodiment, T12 to T15 are the same as or different from each other, each independently hydrogen; deuterium; a halogen group; cyano group; methyl substituted or unsubstituted with deuterium; ethyl substituted or unsubstituted with deuterium; a propyl group substituted or unsubstituted with deuterium; butyl substituted or unsubstituted with deuterium; trimethylsilyl substituted or unsubstituted with deuterium; a butyldimethylsilyl group substituted or unsubstituted with deuterium; a dimethylphenylsilyl group substituted or unsubstituted with deuterium; methyl diphenylsilyl substituted or unsubstituted with deuterium; a triphenylsilyl group 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; a naphthyl group substituted or unsubstituted with deuterium; or a pyridyl group substituted or unsubstituted with deuterium, or a combination with an adjacent group to form hexene substituted or unsubstituted with deuterium or methyl, or benzene substituted or unsubstituted with deuterium or methyl.
In another embodiment, T16 and T17 are the same or different from each other, each independently hydrogen, deuterium, or a substituted or unsubstituted methyl group.
In an embodiment of the present specification, ar11 to Ar14 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.
In another embodiment, ar11 through Ar14 are the same or different from each other and 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 through Ar14 are the same or different from each other and 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 or different from each other and 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, or adjacent 2 groups are bonded to each other to form an aliphatic hydrocarbon ring of 3 to 20 carbon atoms substituted or unsubstituted with deuterium and an aromatic hydrocarbon ring of 6 to 20 carbon atoms fused or not.
In another embodiment, ar11 to Ar14 are the same or different from each other, each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, phenyl substituted or unsubstituted with deuterium, or pyridinyl, or adjacent 2 groups combine with each other to form cyclohexane or tetrahydronaphthalene.
In one embodiment of the present specification, 2 of Ar11 to Ar14 are the same or different from each other, and 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 are the same or different from each other, each is independently hydrogen, deuterium-substituted or unsubstituted methyl, deuterium-substituted or unsubstituted phenyl, or pyridinyl, and the remaining 2 are combined with each other to form cyclohexane or tetrahydronaphthalene.
In an embodiment of the present specification, T18 to T21 apply to the above description about Ar11 to Ar 14.
In another embodiment, T18 to T21 are the same or different from each other and 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 are the same or different from each other and are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, phenyl substituted or unsubstituted with deuterium, or pyridinyl.
In one embodiment of the present specification, T22 applies to the description above for Ar11 to Ar 14.
In another embodiment, T22 is hydrogen, deuterium, or an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium, or adjacent 2 groups combine with each other to form an aromatic hydrocarbon ring of 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 combine with each other to form benzene substituted or unsubstituted with deuterium.
In one embodiment of the present description, t22 is an integer from 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 the above chemical formula 1-A.
In one embodiment of the present specification, R5 is represented by the above chemical formula 1-A.
In one embodiment of the present specification, R6 is represented by the above chemical formula 1-A.
In one embodiment of the present specification, R7 is represented by the above chemical formula 1-A.
In one embodiment of the present specification, R8 is represented by the above chemical formula 1-A.
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 the above chemical formula 1-B.
In one embodiment of the present specification, R5 is represented by the above chemical formula 1-B.
In one embodiment of the present specification, R6 is represented by the above chemical formula 1-B.
In one embodiment of the present specification, R7 is represented by the above chemical formula 1-B.
In one embodiment of the present specification, R8 is represented by the above chemical formula 1-B.
In one embodiment of the present description, n4 and n5 are each integers from 0 to 4. In another embodiment, n4 and n5 are each integers from 0 to 2.
In one embodiment of the present description, n6 is an integer from 0 to 3. In another embodiment, n6 is 0 or 1.
In one embodiment of the present description, n7 and n8 are each integers from 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.
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Next, chemical formula 3 is 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 heterocyclyl.
In one embodiment of the present specification, HAr is a substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted benzimidazolyl.
In one embodiment of the present specification, HAr is represented by any one of the following chemical formulas A1 to A5.
[ chemical formula A1]
[ chemical formula A2]
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[ chemical formula A3]
[ chemical formula A4]
[ chemical formula A5]
In the above chemical formulas A1 to A5,
x1 to X3 are identical to or different from each other and are each, independently of one another, N, CH or CD,
at least one of X1 to X3 is N,
ar22 and Ar23 are the same as or different from each other, each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
r21 to R26 are the same or different from each other and 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 brackets of 2 or more are the same or different from each other.
The broken line is a portion connected to L21.
In one embodiment of the present specification, the chemical formula A1 is any one selected from the following chemical formulas.
In the above chemical formula, the broken lines, ar22 and Ar23 are as defined in chemical formula A1.
In one embodiment of the present specification, the chemical formula A2 is any one selected from the following chemical formulas.
In the above chemical formula, the broken lines, R21 and n21 are as defined in chemical formula A2.
In one embodiment of the present specification, the chemical formula A3 is any one selected from the following chemical formulas.
In the above chemical formula, the broken lines, R22 and n22 are as defined in chemical formula A3.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms and having 2 to 4 valencies, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms and having 2 to 4 valencies.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms and having 2 to 4 valencies, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms and having 2 to 4 valencies.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; or one selected from the group consisting of a substituted or unsubstituted phenyl group having a valence of 2 to 4, a substituted or unsubstituted biphenyl group having a valence of 2 to 4, a substituted or unsubstituted terphenyl group having a valence of 2 to 4, a substituted or unsubstituted tetrabiphenyl group having a valence of 2 to 4, and a substituted or unsubstituted naphthyl group having a valence of 2 to 4; or a 2-valent group formed by connecting 2 or more groups selected from the above groups.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; or one selected from the group consisting of a substituted or unsubstituted phenyl group having a valence of 2 to 4, a substituted or unsubstituted biphenyl group having a valence of 2 to 4, a substituted or unsubstituted terphenyl group having a valence of 2 to 4, a substituted or unsubstituted tetrabiphenyl group having a valence of 2 to 4, and a substituted or unsubstituted naphthyl group having a valence of 2 to 4; or a 2-valent group formed by connecting 2 groups selected from the above groups.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenyl group having 2 to 4 valences, a substituted or unsubstituted biphenyl group having 2 to 4 valences, a substituted or unsubstituted terphenyl group having 2 to 4 valences, a substituted or unsubstituted tetrabiphenyl group having 2 to 4 valences, or a substituted or unsubstituted naphthyl group having 2 to 4 valences.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; or a monocyclic or polycyclic 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, cyano, aryl group having 6 to 30 carbon atoms and heterocyclic group having 2 to 30 carbon atoms, or with 2 or more substituents selected from the group.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; or a monocyclic or polycyclic 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, cyano, aryl group having 6 to 20 carbon atoms and heterocyclic group having 2 to 20 carbon atoms, or with 2 or more substituents selected from the group.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; phenyl substituted or unsubstituted with deuterium, cyano, phenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl or pyridinyl, having a valence of 2 to 4; biphenyl of 2 to 4 valences substituted or unsubstituted with deuterium, cyano or pyridyl; terphenyl of valency 2 to 4, substituted or unsubstituted with deuterium or cyano; a 2-to 4-valent tetrabiphenyl group substituted or unsubstituted with deuterium or cyano; or a 2-to 4-valent naphthyl group substituted or unsubstituted with deuterium or cyano.
In one embodiment of the present description, a is 1 or 2.
In one embodiment of the present description, b is 1 or 2.
In one embodiment of the present specification, the above 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 as defined in chemical formula 3 above,
HAr1 to HAr3 are as defined above for HAr,
l24 is a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
l25 is a substituted or unsubstituted aryl group of 3 valency, or a substituted or unsubstituted heterocyclic group of 3 valency.
In one embodiment of the present specification, L24 and L25 apply to the description above for L21.
In one embodiment of the present specification, formula 3 above-L22- (CN) b Selected from the following structures.
In the above-described structure, the first and second heat exchangers,
l23 is a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
r51 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or 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 a position connected to Ar 21.
In one embodiment of the present description, L23 is a directly bonded, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present description, L23 is a directly bonded, or 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 description, R51 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl.
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; aryl having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano groups, aryl having 2 to 30 carbon atoms and heterocyclic groups having 2 to 30 carbon atoms, or substituents selected from 2 or more groups in the above group.
In one embodiment of the present description, R51 is hydrogen; deuterium; aryl having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano groups, aryl having 2 to 20 carbon atoms and heterocyclic groups having 2 to 25 carbon atoms, or substituents selected from 2 or more groups in the above group.
In one embodiment of the present description, R51 is hydrogen; deuterium; aryl with 6 to 20 carbon atoms which is substituted or unsubstituted by cyano, aryl with 2 to 25 carbon atoms or heterocyclic group with 2 to 25 carbon atoms.
In one embodiment of the present description, R51 is hydrogen; deuterium; phenyl substituted or unsubstituted with cyano or pyridyl; fluorenyl substituted or unsubstituted with phenyl; phenanthryl; dibenzofuranyl; dibenzothienyl; spiro [ fluorene-xanthene ] groups; or a spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, ar21 is a directly bonded, substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or-O-.
In one embodiment of the present specification, ar21 is a directly bonded, substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 25 carbon atoms, or-O-.
In one embodiment of the present specification, ar21 is a directly bonded, substituted or unsubstituted monocyclic arylene group having 6 to 20 carbon atoms, substituted or unsubstituted polycyclic arylene group having 10 to 25 carbon atoms, substituted or unsubstituted polycyclic heterocyclic group having 12 to 25 carbon atoms, or-O-.
In one embodiment of the present specification Ar21 is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted binaphthyl, substituted or unsubstituted fluorenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl of valence 2, substituted or unsubstituted dibenzothienyl of valence 2, substituted or unsubstituted spiro [ fluorene-xanthene ] yl of valence 2, substituted or unsubstituted spiro [ fluorene-thioxanthene ] yl of valence 2, or-O-.
In one embodiment of the present disclosure, ar21 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is substituted or unsubstituted 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 with substituents selected from 2 or more groups in the above group; a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms and having 2 valencies; or-O-.
In one embodiment of the present disclosure, 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; polycyclic arylene groups having 10 to 25 carbon atoms substituted or unsubstituted with alkyl groups having 1 to 6 carbon atoms or aryl groups having 6 to 20 carbon atoms; a heterocyclic group having 2 valencies and a polycyclic group having 12 to 25 carbon atoms; or-O-.
In one embodiment of the present description, ar21 is phenylene substituted or unsubstituted with diphenylfluorenyl, spiro [ fluorene-xanthenyl ] or spiro [ fluorene-thioxanthenyl ] groups; biphenylene substituted or unsubstituted with diphenylfluorenyl, spiro [ fluorene-xanthenyl ] group or spiro [ fluorene-thioxanthenyl ] group; a terphenylene group substituted or unsubstituted with a diphenylfluorenyl, spiro [ fluorene-xanthenyl ] group or spiro [ fluorene-thioxanthenyl ] group; a naphthylene group; a binaphthyl group; fluorenylene substituted or unsubstituted with methyl or phenyl; a spirobifluorenyl group; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; spiro [ fluorene-xanthene ] group of valence 2; spiro [ fluorene-thioxanthene ] group of valence 2; or-O-.
In one embodiment of the present specification, ar21 is a direct bond, phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, spirobifluorenylene.
In one embodiment of the present description Ar21 is-O-, or is selected from the structures described below.
In the above-described structure, the first and second heat exchangers,
x4 and X5 are identical to or different from each other and are each independently CR52R53, O or S,
r27 to R30, R52 and R53 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n27, n28', n29 and n30 are each integers from 0 to 4,
n29 'and n30' are each integers of 0 to 3,
n29 "and n30" are each integers from 0 to 2,
n28+n28' is 6 or less,
n27, n28 to n30, and n28 'to n30' are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other,
n29 'and n30' are each 2, the substituents in brackets are the same or different from each other,
the dotted line is the position where the above-mentioned L21 or L22 is connected.
In one embodiment of the present disclosure, X4 is O or S.
In one embodiment of the present disclosure, X5 is CR52R53.
In one embodiment of the present disclosure, X5 is O or S.
In one embodiment of the present description, R52 and R53 are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R52 and R53 are the same or different from each other, and 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 are the same or different from each other, and are each independently methyl substituted or unsubstituted with deuterium, or phenyl substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R27 to R30 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R27 to R30 are the same or different from each other, and 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.
In one embodiment of the present specification, R27 to R30 are the same or different from each other, and 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 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 are the same or different from each other, and are each independently hydrogen, deuterium, fluorenyl substituted or unsubstituted by methyl or phenyl, spirobifluorenyl substituted or unsubstituted, spiro [ fluorene-xanthene ] substituted or unsubstituted, spiro [ fluorene-thioxanthene ] substituted or unsubstituted.
In one embodiment of the present specification, R27 is hydrogen, deuterium, fluorenyl substituted or unsubstituted with methyl or phenyl, spirobifluorenyl substituted or unsubstituted spiro [ fluorene-xanthene ] yl substituted or unsubstituted spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, R28 to R30 are the same or different from each other, and each is 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 heterocyclyl. Specifically, the substituent attached 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 2-valence) 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 heterocyclyl. Specifically, the substituent attached to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the biphenylene 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 heterocyclyl. Specifically, the substituent attached 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 heterocyclyl. Specifically, the substituent attached to the above-mentioned L21, L22, L24 or Ar24 is substituted or unsubstituted.
In one embodiment of the present specification, the binaphthyl group (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 heterocyclyl. Specifically, the substituent attached 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 an embodiment of the present specification, ar22 and Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In an embodiment of the present specification, ar22 and Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl 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 are the same or different from each other, and 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 description, ar22 and Ar23 are the same or different from each other and are each independently phenyl, biphenyl, spiro [ fluorene-xanthene ] group, or spiro [ fluorene-thioxanthene ] group.
In one embodiment of the present specification, R21 to R26 are the same or different from each other, and 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 one embodiment of the present specification, R21 to R26 are the same or different from each other, and 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 are the same or different from each other, and 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 an embodiment of the present specification, R21 to R26 are the same or different from each other, and are each independently hydrogen, deuterium-substituted or unsubstituted methyl group, deuterium-substituted or unsubstituted ethyl group, deuterium-substituted or unsubstituted tert-butyl group, deuterium-substituted or unsubstituted phenyl group, deuterium-substituted or unsubstituted biphenyl group, or deuterium-substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, R21 to R26 are the same or different from each other and are each independently hydrogen, deuterium, methyl, ethyl, tert-butyl, phenyl, biphenyl or naphthyl.
In one embodiment of the present specification, R22 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.
In one embodiment of the present description, R23 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.
In one embodiment of the present description, R25 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.
In one embodiment of the present specification, R21, R24 and R26 are the same or different from each other, and are each 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.
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According to an embodiment of the present invention, the compounds of the above chemical formulas 1 and 2 may be manufactured as shown in the following reaction formula 1, and the compound of the above chemical formula 3 may be manufactured as shown in the following reaction formula 2. The following equations 1 and 2 describe the synthesis process of a part of the compounds corresponding to the formulas 1 to 3 of the present application, but various compounds corresponding to the formulas 1 to 3 of the present application may be synthesized using the synthesis process shown in the equations 1 and 2, substituents may be combined by a method known in the art, and the kinds, positions and number of substituents may be changed according to a technique known in the art.
[ reaction type 1]
[ reaction type 2]
In the above reaction scheme 1, A 1 To A 3 R represents a substituent attached to the nucleus and may be R1 to R8, A1 or A2 in the present invention. In the above reaction formula 2, the substituents are defined as above.
The organic light emitting device of the present specification can be manufactured by a general manufacturing method and materials of an organic light emitting device, except that the first organic layer is formed using the compound represented by chemical formula 1 or 2 and the second organic layer is formed using the compound represented by chemical formula 3.
The first organic layer containing the compound represented by the above chemical formula 1 or 2 and the second organic layer containing the compound represented by the above chemical formula 3 may be formed not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be constituted by a structure including only the first organic layer and the second organic layer, or may be constituted by a structure further including other organic layers. The other organic layers may be 1 or more layers of 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 may include a smaller or larger number of organic layers.
In the organic light emitting device according to an embodiment of the present disclosure, 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 the 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 an 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 an 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 contained in an amount of 1 to 50 parts by weight, preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight, with respect to 100 parts by weight of the host. Within the above range, energy transfer from the host to the dopant effectively occurs.
In one embodiment of the present specification, the host is an anthracene derivative.
In one embodiment of the present specification, the organic layer includes 2 or more light emitting layers, and 1 layer of the 2 or more light emitting layers includes a compound represented by the chemical formula 1 or 2.
In one embodiment of the present specification, the maximum emission peaks of the light emitting layers of the 2 or more 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 including no 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, the light emitting layer including the compound represented by the above chemical formula 1 or 2 includes a fluorescent dopant, and the light emitting layer including no compound represented by the above chemical formula 1 or 2 includes a phosphorescent dopant.
In one embodiment of the present specification, the maximum light emission peak of the light emitting layer including the compound represented by the above chemical formula 1 or 2 is 400nm to 500nm. 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, one light emitting layer (light emitting layer 1) has a maximum light emission peak of 400nm to 500nm, and the other light emitting layer (light emitting layer 2) may have a maximum light emission peak of 510nm to 580nm, or 610nm to 680 nm. At this time, the light emitting layer 1 includes a compound represented by the above chemical formula 1 or 2.
In the organic light emitting device according to an embodiment of the present specification, the second organic layer is an electron transport 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 transporting layer, an electron injecting layer, and 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, 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 an embodiment of the present disclosure, the second organic layer further includes 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals.
When an organic alkali metal compound or an organic alkaline earth metal compound is used as the n-type dopant, stability of holes in the light emitting layer can be ensured, and thus the life of the organic light emitting device can be improved. In addition, the electron mobility of the electron transporting 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 for the second organic layer.
The second organic layer may include the compound of chemical formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the compound of formula 2 above and the n-type dopant above may be contained in 2:8 to 8:2, and more preferably, may be contained in 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.
According to 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 have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode 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 injection and transport layer 8.
Fig. 8 illustrates a substrate 1 laminated in this order; an anode 2; a p-doped hole transport layer 4p; hole transport layers 4R, 4G, 4B; light emitting layers 6RP, 6GP, 6BF; a first electron transport layer 9a; a second electron transport layer 9b; an electron injection layer 10; the structure of the organic light emitting device of the cathode 11 and the overcoat 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 layers 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 specification, the organic light emitting device may have a serial structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be formed by bonding the respective organic light emitting devices by the charge generating layer. Based on the same brightness, the device of the series structure can be driven at a lower current than the unit device, and thus has an advantage of greatly improving the lifetime characteristics of the device.
According to an embodiment of the present disclosure, the organic layer includes: a first stack including 1 or more light-emitting layers; a second stack including 1 or more light-emitting layers; and a charge generation layer having 1 or more layers between the first stack and the second stack.
According to an embodiment of the present disclosure, the organic layer includes: a first stack including 1 or more light-emitting layers; a second stack including 1 or more light-emitting layers; and a third stack including 1 or more light-emitting layers, each including 1 or more charge generating layers between the first stack and the second stack, and between the second stack and the third stack.
In this specification, the charge generation 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 means a charge generation layer provided closer to the anode than the P-type charge generation layer, and the P-type charge generation layer means 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 first stack, the second stack, and the 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 that performs hole transport and hole injection simultaneously (hole injection and transport layers), and a layer that performs electron transport and electron injection simultaneously (electron injection and transport layers).
An organic light emitting device including the above-described first and second stacks 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.
An organic light emitting device including the above-described first to third stacks is illustrated in fig. 4 to 7.
Fig. 4 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, 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 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-transporting layers 9a, 9b, and 9 c.
Fig. 5 illustrates a structure of an organic light emitting device in which the substrate 1, the anode 2, the hole injection layer 3, the first hole transport layer 4a, the second hole transport layer 4b, the first blue fluorescent light emitting layer 6BFa, the first electron transport layer 9a, the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the red phosphorescent light emitting layer 6RP, the yellow green phosphorescent light emitting layer 6YGP, the green phosphorescent light emitting layer 6GP, the second electron transport layer 9b, the second N-type charge generation layer 12b, the second P-type charge generation layer 13b, the fourth hole transport layer 4d, the fifth hole transport layer 4e, the second blue fluorescent light emitting layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked. In the structure 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 the substrate 1, the anode 2, the hole injection layer 3, the first hole transport layer 4a, the second hole transport layer 4b, the first blue fluorescent light emitting layer 6BFa, the first electron transport layer 9a, the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the red phosphorescent light emitting layer 6RP, the green phosphorescent light emitting layer 6GP, the second electron transport layer 9b, the second N-type charge generation layer 12b, the second P-type charge generation layer 13b, the fourth hole transport layer 4d, the fifth hole transport layer 4e, the second blue fluorescent light emitting layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked. In the structure 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 the substrate 1, the anode 2, the first P-doped hole transport layer 4pa, the first hole transport layer 4a, the second hole transport layer 4b, the first blue fluorescent light emitting layer 6BFa, the first electron transport layer 9a, the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the fourth hole transport layer 4d, the second blue fluorescent light emitting layer 6BFb, the second electron transport layer 9b, the second N-type charge generation layer 12b, the second P-type charge generation layer 13b, the fifth hole transport layer 4e, the sixth hole transport layer 4f, the third blue fluorescent light emitting layer 6BFc, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked. In the structure described above, the compound represented by the above chemical formula 1 or 2 may be contained in 1 or more layers among the first, second, and third blue fluorescent light-emitting layers 6BFa, 6BFb, and 6BFb, and the compound represented by the above chemical formula 3 may be contained in 1 or more layers among the first, second, third, and electron injection layers 9a, 9b, 9c, and 10.
The N-type charge generation layer may be 2,3,5, 6-tetrafluoro-7, 8-tetracyanodimethyl-p-benzoquinone (F4 TCNQ), fluoro-substituted 3,4,9, 10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalene tetracarboxylic dianhydride (NTCDA), fluoro-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylamine derivative, or the like, but is not limited thereto. In one embodiment, the N-type charge generating layer may include both a benzimidazole phenanthrene 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 may be manufactured using materials and methods known in the art, except that the organic layer includes 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 material or different materials. The organic light emitting device according to the present specification may be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate, an organic layer including the first organic layer and the second organic layer is formed on the anode, and a substance which can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer including the first organic layer and the 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 may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to 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, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathodeAs the cathode material, an electrode that injects electrons is generally preferred to have a small work function in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and has a single layer or a multilayer structure of 2 or more layers. The hole injecting substance is a substance that can well inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. 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 from each other.
The hole transport layer can be a single layer or a multilayer structure of 2 or more layers, and can function to smooth hole transport. 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 a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions. 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 from each other.
The hole injection and transport layer is a layer that performs hole transport and hole injection simultaneously, and a hole transport layer material and/or a hole injection layer material known in the art may be used.
The electron injection and transport layer is a layer that performs electron transport and electron injection simultaneously, and electron transport layer materials and/or electron injection layer materials 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 use materials known in the art.
The light-emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium), tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 (tris (8-hydroxyquinone) aluminum, tris (8-hydroxy)Aluminum quinolinolate), etc., but is not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.
A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
The electron transport layer plays a role in making electron transport smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like.
The electron injection layer plays a role in smoothing electron injection. As the electron injecting substance, the following compounds are preferable: a compound having an electron-transporting ability, an electron-injecting effect from a cathode, an excellent electron-injecting effect to a light-emitting layer or a light-emitting material, and an excellent thin film-forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, and the like thereof, but are not limited thereto。
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
In the following, examples, comparative examples, and the like will be described in detail for the purpose of specifically describing the present specification. 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. Examples and comparative examples of the present description are provided to more fully illustrate the present description 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 above 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, 1.0g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene under nitrogen atmosphere, and then stirred under reflux for 2 hours. After the 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
30g of intermediate 1, 30.5g of N- (5- (tert-butyl) - [1,1' -biphenyl) are reacted under nitrogen]-2-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, 14.2g of sodium t-butoxide, 0.4g of bis (tri-t-butylphosphine) palladium (0) were added to 450ml of toluene, and then stirred under reflux for 2 hours. After the 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, 21.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then, 8g of compound 1 was obtained by recrystallization (yield 32%). MS [ M+H ]] + ＝789
Synthesis example 2 Synthesis of Compound 2
1) Synthesis of intermediate 3
46g of intermediate 3 was obtained by recrystallization from 30g of intermediate 1, 38.6g of N- (4- (tert-butyl) -2- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) phenyl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine using the same materials and equivalent as the synthesis method of intermediate 2. (yield 70%). MS [ M+H ]] + ＝892
2) Synthesis of Compound 2
At nitrogenAfter 25g of intermediate 3 and 20.2g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under an atmosphere, the mixture was stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then, 8.1g of compound 2 was obtained by recrystallization (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, 75.8g of bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 72g of intermediate 4 was obtained by recrystallization using the same substance and equivalent as those of the synthesis method of intermediate 1. (yield 72%). MS [ M+H ]] + ＝515
2) Synthesis of intermediate 5
For 30g of intermediate 4, 20.9g of 5- (tert-butyl) -N- (3- (tert-butyl) phenyl) - [1,1' -biphenyl]The 2-amine was recrystallized using the same materials and equivalent weights as the synthesis of intermediate 2 to yield 39g of intermediate 5. (yield 80%). MS [ M+H ]] + ＝840
3) Synthesis of Compound 3
25g of intermediate 5, 19.9g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then, 8.1g of compound 3 was obtained by recrystallization (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-phenylpropane-2-yl) phenyl) amine, 36g of intermediate 5 was obtained by recrystallization using the same materials and equivalent as the synthesis method of intermediate 2. (yield 70%). MS [ M+H ]] + ＝884
2) Synthesis of Compound 4
25g of intermediate 5, 18.8g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then, 7.6g of compound 4 was obtained by recrystallization (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 39g of intermediate 6 were obtained by recrystallization using the same substance and equivalent as those of the synthesis method of intermediate 2. (yield 75%). MS [ M+H ]] + ＝890
2) Synthesis of Compound 5
25g of intermediate 6, 18.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then, 7.2g of compound 5 was obtained by recrystallization (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, using the same materials and equivalent weights as the synthesis of intermediate 2, 42g of intermediate 7 was obtained by recrystallization. (yield 75%).
MS[M+H] + ＝966
2) Synthesis of Compound 6
25g of intermediate 7, 17.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then, 7.6g of compound 6 was obtained by recrystallization (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, 33g of intermediate 8 was obtained by recrystallization using the same materials and equivalent as those of the synthesis of intermediate 2. (yield 68%). MS [ M+H ]] + ＝828
2) Synthesis of Compound 7
After adding 25g of intermediate 8, 20.1g of boron triiodide to 250ml of 1, 2-dichlorobenzene under nitrogen, inStirred for 4 hours at 160 ℃. After the completion of the reaction, extraction was performed, and then 7.7g of compound 7 was obtained by recrystallization (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, 8-pentamethyl-N- (5, 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, and then stirred under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then 41.7g of intermediate 9 was obtained by recrystallization. (yield 68%). MS [ M+H ] ] + ＝938
2) Synthesis of Compound 8
25g of intermediate 9, 20.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 150℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.8g of compound 8 was obtained by recrystallization (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 20.3g of intermediate 10 was obtained by recrystallization using the same materials and equivalent as the synthesis of intermediate 2. (yield 69%). MS [ M+H ]] + ＝780
2) Synthesis of Compound 9
15g of intermediate 10, 11g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, and stirred at 150℃for 4 hours. After the completion of the reaction, extraction was performed, and then 5g of compound 9 was obtained by recrystallization (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine 75g of intermediate 11 was obtained by recrystallization using the same materials and equivalent as the synthesis of intermediate 1. (yield 80%). MS [ M+H ] ] + ＝579
2) Synthesis of intermediate 12
40g of intermediate 11, 11.3g of 4-t-butylaniline, 19.9g of sodium t-butoxide and 0.4g of bis (tri-t-butylphosphine) palladium (0) were added to 600ml of toluene, and after refluxing for 1 hour, it was confirmed whether or not the reaction was performed, 13.2g of 1-bromo-3-chlorobenzene was added to the refluxing reaction, and the refluxing reaction was performed for 1 hour. After the completion of the reaction, extraction was performed, and then 28.8g of intermediate 12 was obtained by recrystallization. (yield 52%). MS [ M+H ]] + ＝801
3) Synthesis of intermediate 13
25g of intermediate 12 are reacted under nitrogen,20.4g of boron triiodide was added to 250ml of 1, 2-dichlorobenzene and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 5.5g of intermediate 13 was obtained by recrystallization (yield 22%). MS [ M+H ]] + ＝809
4) Synthesis of Compound 10
5g of intermediate 16, 1.5g of diphenylamine, 1.2g of sodium t-butoxide, and 0.05g of bis (tri-t-butylphosphine) palladium (0) were added to 80ml of xylene, followed by stirring under reflux for 5 hours. After the completion of the reaction, extraction was performed, and then 4.6g of compound 10 was obtained by recrystallization. (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 were reacted with ]After adding 2-amine, 22.4g of sodium t-butoxide and 0.4g of bis (tri-t-butylphosphine) palladium (0) to 600ml of toluene, the mixture was refluxed for 1 hour, and after confirming whether the reaction had been carried out, 14.9g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was carried out for 1 hour. After the 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, 20.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 8.3g of intermediate 15 was obtained by recrystallization (yield 33%). MS [ M+H ]] + ＝822
3) Synthesis of Compound 11
7g of intermediate 15, 3.4g of bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 1.7g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, and then stirred under reflux for 5 hours. After the completion of the reaction, extraction was performed, and then 7.4g of compound 11 was obtained by recrystallization. (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, 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 equivalent as the synthesis method of intermediate 1]-2-yl) (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amino) -5-chlorophenol. (yield 57%). MS [ M+H ]] + ＝539
40g of 3- ((5- (tert-butyl) - [1,1' -biphenyl ] -2-yl) (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amino) -5-chlorophenol 20ml of 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride and 30g of potassium carbonate were added to 400ml of tetrahydrofuran and 200ml of water, after the reaction was completed for 3 hours, extraction was performed, and then, the solution was removed, thereby obtaining 58g of intermediate 16. (yield 97%).
2) Synthesis of intermediate 17
40g of intermediate 16, 14g of bis (4- (tert-butyl) phenyl) amine, 0.85g of Pd (d) are reacted under a nitrogen atmosphereba) 2 After 1.42g of Xphos (2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl) and 48.6g of cesium carbonate were added to 500ml of xylene, the mixture was refluxed and stirred for 24 hours. After the completion of the reaction, extraction was performed, and then 31g of intermediate 17 was obtained by recrystallization (yield 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 and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.9g of intermediate 18 was obtained by recrystallization (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 t-butoxide, 0.05g of bis (tri-t-butylphosphine) palladium (0) were added to 80ml of xylene, and then stirred under reflux for 5 hours. After the 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]After furan-1-amine, 22.4g of sodium t-butoxide and 0.4g of bis (tri-t-butylphosphine) palladium (0) were added to 600ml of toluene, the mixture was refluxed for 1 hour, and after confirming whether or not the reaction was performed, 20.8g of 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene was added to the reflux reaction, and the reflux reaction was performed for 1 hour. After the completion of the reaction, extraction is performed, followed by recrystallization54g of intermediate 19 are obtained. (yield 82%). MS [ M+H ]] + ＝848
2) Synthesis of Compound 13
25g of intermediate 19, 19.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then, 7.5g of compound 13 was obtained by recrystallization (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 was recrystallized using the same materials and equivalent weights as the synthesis of intermediate 19 to yield 54g of intermediate 20. (yield 78%). MS [ M+H ]] + ＝864
2) Synthesis of Compound 14
25g of intermediate 20, 19.3g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.6g of compound 14 was obtained by recrystallization (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]Furan4-Bromide 11.6g of 3- (tert-butyl) aniline 50g of intermediate 21 were obtained by recrystallisation using the same materials and equivalents as the synthesis of intermediate 19. (yield 76%). MS [ M+H ]] + ＝850
2) Synthesis of Compound 15
After adding 25g of intermediate 21, 21g of boron triiodide to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, stirring was carried out at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then, 8.3g of compound 15 was obtained by recrystallization (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]After furan-1-amine, 22.4g of sodium t-butoxide and 0.4g of bis (tri-t-butylphosphine) palladium (0) were added to 600ml of toluene, the mixture was refluxed for 1 hour, and after confirming whether or not the reaction was performed, 14.9g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was performed for 1 hour. After the completion of the reaction, extraction was performed, and then 46g of intermediate 22 was obtained by recrystallization. (yield 77%). MS [ M+H ]] + ＝771
2) Synthesis of intermediate 23
25g of intermediate 22, 21.6g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.8g of intermediate 23 was obtained by recrystallization (yield 31%). MS [ M+H ]] + ＝780
3) Synthesis of Compound 16
7g of intermediate 23, 1.8g of 4a,9 a-dimethyl-2, 3, 4a,9 a-hexahydro-1H-carbazole, 1.7g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, and the mixture was stirred under reflux for 5 hours. After the 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, 8-tetramethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -5,6,7, 8-tetrahydronaphthalen-2-amine 17.9g of 3,5, 8-pentamethyl-N- (m-tolyl) -5,6,7, 8-tetrahydronaphthalen-2-amine were prepared using the same materials and equivalents as in the synthesis of intermediate 2, 31.3g of intermediate 24 was obtained by recrystallization. (yield 69%). MS [ M+H ]] + ＝789
2) Synthesis of Compound 17
25g of intermediate 24, 20.4g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then, 7g of compound 17 was obtained by recrystallization (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) were reacted with]After adding (E) -2-yl) -N- (3-chloro-5-methylphenyl) -1, 3-tetramethyl-2, 3-dihydro-1H-inden-5-amine, 12.1g of 4- (t-butyl) -2-methylaniline, 22.1g of sodium t-butoxide and 0.4g of bis (tri-t-butylphosphine) palladium (0) to 600ml of toluene, the mixture was refluxed for 1 hour, and after confirming whether the reaction was performed, 14.6g of 1-bromo-3-chlorobenzene was added to the reflux reaction, and the reflux reaction was further performed for 1 hour. After the 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
After adding 25g of intermediate 25, 21.9g of boron triiodide to 250ml of 1, 2-dichlorobenzene under nitrogen, stirring was carried out at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.1g of intermediate 26 was obtained by recrystallization (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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, and the mixture was stirred under reflux for 5 hours. After the 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
Use of 40g of 3-bromo-5-chlorophenol, 75.2g of bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amineThe same substance and equivalent as those of the intermediate 35 were obtained by recrystallization, 70g of the intermediate 27 was obtained. (yield 70%). MS [ M+H ]] + ＝517
The same substance and equivalent as those of the intermediate 16 were used for 40g of the intermediate 27, thereby obtaining 56g of the 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) ]Thiophen-2-yl) phenyl) -3-methyl- [1,1' -biphenyl]The 4-amine was recrystallized using the same materials and equivalent weights as the synthesis of intermediate 17 to yield 54g of intermediate 29. (yield 74%). MS [ M+H ]] + ＝940
3) Synthesis of intermediate 30
25g of intermediate 29, 17.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.5g of intermediate 30 was obtained by recrystallization (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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 80ml of xylene, and then stirred under reflux for 5 hours. After the 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 were obtained by recrystallization under a nitrogen atmosphere, using the same materials and equivalent weights as the synthesis method of intermediate 9, for 40g of 1, 3-dibromo-5-chlorobenzene, 115.3g of bis (5, 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, 18.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.7g of intermediate 32 was obtained by recrystallization (yield 31%). MS [ M+H ]] + ＝896
3) Synthesis of Compound 20
7g of intermediate 32, 3g of bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 1.5g of sodium t-butoxide, 0.04g of bis (tri-t-butylphosphine) palladium (0) were added to 80ml of xylene, and then stirred under reflux for 5 hours. After the completion of the reaction, extraction was performed, and then, 7.1g of compound 20 was obtained by recrystallization. (yield 73%). MS [ M+H ]] + ＝1249
Synthesis example 21 Synthesis of Compound 21
1) Synthesis of intermediate 33
By the same method as that of the intermediate 1 of Synthesis example 1, 25g of bis (3-isopropylbenzene) was usedBase) amine to yield 25g of intermediate 33. (yield 67%). MS [ M+H ]] + ＝378
2) Synthesis of intermediate 34
27.3g of N- (5- (tert-butyl) - [1,1' -biphenyl) was used in the same manner as in the synthesis of intermediate 2 of Synthesis example 1]-2-yl) -9, 10-tetramethyl-9, 10-dihydro-anthracene-2-amine to give 32.2g of intermediate 34. (yield 71%). MS [ M+H ] ] + ＝858
3) Synthesis of Compound 21
25g of intermediate 34, 20.1g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.3g of compound 21 was obtained by recrystallization (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, 4a,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 nitrogen atmosphere, and then stirred under reflux for 5 hours. After the 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
By the same method as that of the intermediate 16 of Synthesis example 12, 35g of di ([ 1,1' -biphenyl ] -3-yl) amine was used to obtain 40.5g of the intermediate 36. (yield 51%).
2) Synthesis of intermediate 37
20.4g of N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] were used in the same manner as in Synthesis example 12, intermediate 17]Furan-1-amine gives 31.8g of intermediate 37. (yield 72%). MS [ M+H ] ] + ＝799
3) Synthesis of intermediate 38
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By the same method as that of intermediate 18 of Synthesis example 12, 11.8g of intermediate 38 was obtained using 30g of intermediate 37. (yield 39%). MS [ M+H ]] + ＝808
3) Synthesis of Compound 23
By the same procedures as those conducted for synthesizing Compound 12 of Synthesis example 12, 7g of intermediate 38, 2.4g of 4a,9 a-dimethyl-6- (trimethylsilyl) -2,3, 4a,9 a-hexahydro-1H-carbazole were used to obtain 6.2g of Compound 23. (yield 69%). MS [ M+H ]] + ＝1045
Synthesis example 24 Synthesis of Compound 24
1) Synthesis of intermediate 39
By synthesis with synthesisThe same procedures as in intermediate 1 of example 1 were conducted using 25g of 3' -bromo-5 ' -chloro-2, 6-dimethyl-1, 1' -biphenyl and 23.8g of bis (3- (tert-butyl) phenyl) amine to obtain 27.3g of intermediate 39. (yield 65%). MS [ M+H ]] + ＝496
2) Synthesis of intermediate 40
By the same procedures as those conducted for synthesizing intermediate 2 of Synthesis example 1, using 22g of intermediate 39 and 17.5g of 9, 9-dimethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-4-amine, 23.9g of intermediate 40 was obtained. (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, 4.2g of Compound 24 was obtained using 20g of intermediate 39. (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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 34.1g of sodium tert-butoxide, 0.9g of bis (tri-tert-butylphosphine) palladium (0) were added to 600ml of toluene under nitrogen atmosphere, and then stirred under reflux for 2 hours. After the completion of the reaction, extraction was performed, and then 70g of intermediate 41 was obtained by recrystallization. (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 reacted under nitrogen]2-amine, 0.4g of bis (tri-t-butylphosphine) palladium (0), 18g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 14.3g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the 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, 20.0g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.4g of intermediate 43 was obtained by recrystallization (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, 4a,9 a-hexahydro-1H-carbazole, 1.6g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then 7.7g of compound 25 was obtained by recrystallization. (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, 4a,9 a-hexahydro are reacted under nitrogenAfter adding 1H-carbazole-5, 6,7,8-d4, 1.6g of sodium tert-butoxide and 0.04g of bis (tri-tert-butylphosphine) palladium (0) to 100ml of toluene, the mixture was stirred under reflux for 6 hours. After the 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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] are reacted under nitrogen]After furan-4-amine, 37.4g of sodium t-butoxide, 1.0g of bis (tri-t-butylphosphine) palladium (0) were added to 600ml of toluene, the mixture was stirred under reflux for 2 hours. After the 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 are reacted under nitrogen]Furan-4-amine, 0.4g of bis (tri-t-butylphosphine) palladium (0), 19g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 15.5g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the 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
After adding 25g of intermediate 45, 22.1g of boron triiodide to 250ml of 1, 2-dichlorobenzene under nitrogen, stirring was carried out at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.7g of intermediate 46 was obtained by recrystallization (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, 4a,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 nitrogen atmosphere, and then stirred under reflux for 6 hours. After the 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, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] are reacted under nitrogen]After furan-1-amine, 37.4g of sodium t-butoxide, 1.0g of bis (tri-t-butylphosphine) palladium (0) were added to 600ml of toluene, the mixture was stirred under reflux for 2 hours. After the 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 are reacted under nitrogen]Thiophene-4-amine, 0.4g of bis (tri-t-butylphosphine) palladium (0) was added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 15.5g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the reaction, extraction is performed, and then, recrystallization is performed44g of intermediate 48 were obtained. (yield 71%). MS [ M+H ]] + ＝768
3) Synthesis of intermediate 49
25g of intermediate 48, 21.7g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.4g of intermediate 49 was obtained by recrystallization (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, 4a,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 nitrogen atmosphere, and then stirred under reflux for 6 hours. After the 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
After 20g of 1, 3-dibromo-5-chlorobenzene, 41.6g of bis (4- (t-butyl) phenyl) amine, 35.5g of sodium t-butoxide, 0.4g of bis (tri-t-butylphosphine) palladium (0) were added to 300ml of toluene under nitrogen atmosphere, the mixture was stirred under reflux for 2 hours. After the 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, 24.8g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.4g of intermediate 51 was obtained by recrystallization (yield 29%). MS [ M+H ]] + ＝680
3) Synthesis of Compound 29
7g of intermediate 51, 2.1g of 4a,9 a-dimethyl-2, 3, 4a,9 a-hexahydro-1H-carbazole, 2.0g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the 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
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26.6g of intermediate 52 was obtained by the same method as in production of intermediate 5 of Synthesis example 3 using 15g of bis (4-cyclohexylphenyl) amine. (yield 73%). MS [ M+H ]] + ＝812
By the same method as that for producing Compound 3 of Synthesis example 3, 9.2g of Compound 30 was obtained using 20g of intermediate 52. (yield 46%). MS [ M+H ]] + ＝820
Synthesis example 31 Synthesis of intermediate 53
Will be charged with starting material B1 (20 g,1 eq), bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydro-naphthalen-2-yl) amine (35.6 g,2.05 eq), pd (PtBu) 3 ) 2 (1.1g0.05 eq), naOtBu (12.8 g,3 eq) and toluene (250 ml) were heated at 110℃and stirred for 6 hours. The reaction mixture was cooled to room temperature, water and toluene were then added thereto, and after separation, the solvent was distilled off under reduced pressure. Purification by recrystallization (toluene/hexane) afforded intermediate 53 (30.9 g). (yield 65%). MS [ M+H ]] + ＝1066
Synthesis example 32 Synthesis of Compound 31
N-butyllithium pentane solution (18.7 ml,2.5M in hexane solution (2.5M in hexane), 2 equivalents) was added to a flask containing intermediate 53 (25 g) and toluene (150 ml) under argon at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 50℃and stirred for 2 hours. Cooled to-40 ℃, boron tribromide (3.4 ml,1.5 eq.) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0℃again, N-diisopropylethylamine (10 ml) was added thereto, and the reaction mixture was stirred at room temperature for a further 30 minutes. Saturated NaCl solution (Sat. Aq. NaCl) and ethyl acetate were added, and after separation, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (toluene/hexane) to obtain compound 31 (6.3 g). (yield 27%). MS [ M+H ] ] + ＝996
Synthesis example 33 Synthesis of Compound 2-1
1) Synthesis of intermediate 55
Intermediate 54 (41 g, yield 63%) was produced using the starting materials of the above chemical formulas by the same method as that of intermediate 53 of synthesis example 31. MS [ M+H ]] + ＝623
Intermediate 55 (7.5 g, yield 49%) was obtained using 15g of intermediate 54 by the same method as the method for producing compound 3 of synthesis example 3. MS [ M+H ]] + ＝631
2) Synthesis of Compound 2-1
By the same method as that for synthesizing Compound 29 of Synthesis example 29, compound 2-1 (8.6 g, yield 77%) was obtained using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝778
Synthesis example 34 Synthesis of Compound 2-2
1) Synthesis of intermediate 72
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40g of A2, 50.1g of 6- (tert-butyl) -4a,9 a-dimethyl-2, 3, 4a,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 nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then, 52g of intermediate 72 was obtained by column purification. (yield 70%). MS [ M+H ]] + ＝383
2) Synthesis of intermediate 57
Intermediate 56 (39.5 g, 59% yield) was obtained by the same method as that of intermediate 48 of synthesis example 28 using the starting materials of the above chemical formulas. MS [ M+H ] ] + ＝695
Intermediate 57 (8.5 g, 44% yield) 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
The above method was used in the same manner as in the synthesis of Compound 29 of Synthesis example 29Starting material of the formula gave compound 2-2 (6.9 g, 71% yield). MS [ M+H ]] + ＝865
Synthesis example 35 Synthesis of Compounds 2-3
1) Synthesis of intermediate 73
40g of intermediate 72, 20.9g of dibenzo [ b, d are reacted under nitrogen]Thiophene-4-amine, 0.6g of bis (tri-t-butylphosphine) palladium (0), 25.2g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 20.1g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then 54g of intermediate 73 was obtained by recrystallization. (yield 79%). MS [ M+H ]] + ＝656
2) Synthesis of intermediate 74
After adding 25g of intermediate 73, 25.4g of boron triiodide to 250ml of 1, 2-dichlorobenzene under nitrogen, stirring was carried out at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.4g of intermediate 74 was obtained by recrystallization (yield 29%). MS [ M+H ] ] + ＝664
2) Synthesis of Compound 2-3
By the same method as that of Compound 29 of Synthesis example 29, compound 2-3 (6.9 g, yield 74%) was obtained using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝886
Synthesis example 36 Synthesis of Compounds 2-4
1) Synthesis of intermediate 58
Intermediate 58 (32 g, yield 76%) was obtained using the starting materials of the above chemical formulas by the same method as that of intermediate 72 of synthesis example 34. MS [ M+H ]] + ＝410
2) Synthesis of intermediate 60
Intermediate 59 (20.7 g, yield 62%) was obtained by the same method as the method of synthesizing intermediate 48 of synthesis example 28 using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝701
Intermediate 60 (5.8 g, yield 38%) was obtained using 15g of intermediate 59 by the same method as the method for producing compound 3 of synthesis example 3. MS [ M+H ]] + ＝709.44
3) Synthesis of Compounds 2-4
By the same method as that of Compound 29 of Synthesis example 29, compound 2-4 (4.4 g, yield 66%) was obtained using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝949
Synthesis example 37 Synthesis of Compounds 2-5
1) Synthesis of intermediate 62
Intermediate 61 (26 g, yield 79%) was obtained using the starting materials of the above chemical formulas by the same method as that of intermediate 72 of synthesis example 34. MS [ M+H ] ] + ＝396
Obtained by using the starting materials of the above formula in the same manner as in the intermediate 34 of Synthesis example 21Intermediate 62 (15.9 g, 67% yield) was obtained. MS [ M+H ]] + ＝691
2) Synthesis of Compounds 2-5
By the same method as that for producing Compound 3 of Synthesis example 3, 14g of intermediate 62 was used to obtain Compound 2-5 (5 g, yield 35%). MS [ M+H ]] + ＝699
Synthesis example 38 Synthesis of Compounds 2-6
1) Synthesis of intermediate 64
Intermediate 63 (26.3 g, 76% yield) was obtained using the starting materials of the above formula by the same method as that of intermediate 72 of synthesis example 34. MS [ M+H ]] + ＝424
Intermediate 64 (29.8 g, yield 70%) was obtained by the same method as the method of synthesizing intermediate 34 of synthesis example 21 using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝754
2) Synthesis of Compounds 2-6
Compounds 2 to 6 (7.5 g, 39% yield) were obtained from 19g of the intermediate 64 by the same method as that for producing the compound 3 of Synthesis example 3. MS [ M+H ]] + ＝761
Synthesis example 39 Synthesis of Compounds 2-7
1) Synthesis of intermediate 68
40g of A2, 39.2g of 4a,9 a-dimethyl-2,3, 4a,9 a-hexahydro-1H-carbazole, 1.0g of bis (tri-t-butylphosphine) palladium (0), and 38g of sodium t-butoxide were added to 600ml of toluene, followed by stirring under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then, 49g of intermediate 68 was obtained by column purification. (yield 77%). MS [ M+H ] ] + ＝326
2) Synthesis of intermediate 69
40g of intermediate 68, 22.5g of dibenzo [ b, d ] are reacted under nitrogen]Furan-1-amine, 0.6g of bis (tri-t-butylphosphine) palladium (0), 29.5g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 23.5g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the 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, 28.5g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere, followed by stirring at 160℃for 4 hours. After the completion of the reaction, extraction was performed, and then 7.8g of intermediate 70 was obtained by recrystallization (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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then 7.4g of compound 2-7 was obtained by recrystallization. (yield 75%). MS [ M+H ]] + ＝836
Synthesis example 40 Synthesis of Compounds 2-8
1) Synthesis of intermediate 71
40g of intermediate 68, 22.5g of dibenzo [ b, d ] are reacted under nitrogen]Furan-4-amine, 0.6g of bis (tri-t-butylphosphine) palladium (0), 29.5g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 23.5g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then 54g of intermediate 71 was obtained by recrystallization. (yield 76%). MS [ M+H ]] + ＝584
2) Synthesis of Compounds 2-8
25g of intermediate 71, 28.5g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.6g of intermediate 72 was obtained by recrystallization (yield 30%). MS [ M+H ]] + ＝592
7g of intermediate 72, 3.4g of bis (4- (tert-butyl) phenyl) amine, 2.3g of sodium tert-butoxide, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then 7.6g of compound 2-8 was obtained by recrystallization. (yield 76%). MS [ M+H ]] + ＝836
Synthesis example 41 Synthesis of Compounds 2-9
1) Synthesis of Compounds 2-9
7g of intermediate 72, 4.6g of bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine, 2.3g of sodium t-butoxide, 0.05g of bis (tri-t-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the reaction, extraction is carried out, and then the mixture is subjected to heavy weightCrystallization gave 7.5g of compounds 2-9. (yield 76%). MS [ M+H ]] + ＝945
Synthesis example 42 Synthesis of Compounds 2-10
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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then 7.5g of compound 2 to 10 was obtained by recrystallization. (yield 78%). MS [ M+H ]] + ＝909
Synthesis example 43 Synthesis of Compounds 2-11
1) Synthesis of intermediate 75
40g of A1, 35.7g of 4a,9 a-dimethyl-2, 3, 4a,9 a-hexahydro-1H-carbazole, 0.9g of bis (tri-tert-butylphosphine) palladium (0), 34g of sodium tert-butoxide were added to 600ml of toluene under nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After the completion of the reaction, extraction was performed, and then, 47g of intermediate 75 was obtained by column purification. (yield 77%). MS [ M+H ] ] + ＝347
2) Synthesis of intermediate 76
40g of intermediate 75, 21.2g of dibenzo [ b, d are reacted under nitrogen]Furan-4-amine, 0.6g of bis (tri-t-butylphosphine) palladium (0), 27.8g of sodium t-butoxide were added to 600ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 22.1g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the completion of the reaction, extraction is performed, and then recrystallization is performed to obtain55g of intermediate 76. (yield 79%). MS [ M+H ]] + ＝604
3) Synthesis of Compounds 2-11
25g of intermediate 76, 27.6g of boron triiodide were added to 250ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.2g of intermediate 77 was obtained by recrystallization (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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then 7.9g of compound 2-11 was obtained by recrystallization. (yield 63%). MS [ M+H ]] + ＝1102
Synthesis example 44 Synthesis of Compounds 2-12
1) Synthesis of intermediate 78
40g of intermediate 72, 21.6g of 3,5, 8-pentamethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine, 0.5g of bis (tri-t-butylphosphine) palladium (0), 23.9g of sodium t-butoxide were added to 600ml of toluene under nitrogen atmosphere, and then stirred under reflux for 1 hour. After confirming whether or not the reaction was carried out, 19.1g of 1-bromo-3-chlorobenzene was added during stirring, and then the mixture was stirred under reflux for 4 hours. After the 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, 24.0 are reacted under nitrogenAfter adding g of boron triiodide to 250ml of 1, 2-dichlorobenzene, the mixture was stirred at 160℃for 4 hours. After completion of the reaction, extraction was performed, and then 7.4g of intermediate 79 was obtained by recrystallization (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, 0.05g of bis (tri-tert-butylphosphine) palladium (0) were added to 100ml of toluene under nitrogen atmosphere, and then stirred under reflux for 6 hours. After the completion of the reaction, extraction was performed, and then, 8.3g of compound 2-12 was obtained by recrystallization. (yield 70%). MS [ M+H ]] + ＝1192
Synthesis example 45 Synthesis of Compounds 2-13
22g of intermediate 80 was obtained by the same method as that of the intermediate 17 of Synthesis example 12 using intermediate 28 and 4a,5,7,9 a-tetramethyl-6-phenyl-2, 3, 4a,9 a-hexahydro-1H-carbazole. (yield 61%). MS [ M+H ]] + ＝804
Intermediate 81 (5.9 g, 29%) was obtained using 20g of intermediate 80 by the same method as the method for producing compound 3 of synthesis example 3. MS [ M+H ]] + ＝811
By the same method as that of Compound 29 of Synthesis example 29, compound 2-13 (5.4 g, yield 68%) was obtained using the starting materials of the above chemical formulas. MS [ M+H ]] + ＝1097
Synthesis example 46 Synthesis of Compound 32
16.3g of intermediate 82 was obtained by using the substance of the above chemical formula in the same manner as in the production method of intermediate 5 of Synthesis example 3. (yield 77%). MS [ M+H ]] + ＝647
Obtained by 16g of intermediate 82 in the same manner as in the production of Compound 3 in Synthesis example 35.3g of compound 32 were obtained. (yield 33%). MS [ M+H ]] + ＝655
Synthesis example 47 Synthesis of Compound 33
1) Synthesis of intermediate 84
32g of intermediate 83 was obtained by using the substance of the above chemical formula in the same manner as in the method for producing intermediate 31 of Synthesis example 20. (yield 71%). MS [ M+H ] ] + ＝663
10g of intermediate 84 was obtained by using the substance of the above chemical formula in the same manner as in the method for producing intermediate 32 of Synthesis example 20. (yield 32%). MS [ M+H ]] + ＝671
2) Synthesis of Compound 33
By the same method as that for producing Compound 20 of Synthesis example 20, 8.5g of Compound 33 was obtained using the substance of the above chemical formula. (yield 70%). MS [ M+H ]] + ＝913
The present specification also provides a method for manufacturing an organic light-emitting device formed 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 ] are added]After 380mL of tetrahydrofuran and 50mL of water, 1.1g of tetrakis (triphenylphosphine) palladium (0) [ tetrakis (triphenylhosphine) paladium (0) was added]Pd(PPh 3 ) 4 After that, the mixture was heated and stirred for 8 hours. After the reaction, the reaction mixture was cooled to room temperature, the organic solvent was removed, dissolved in toluene and extracted, and the organic solvent was then extracted with MgSO 4 (none)Water (android)) is treated 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%, MS [ M+H) ] + ＝613)
Synthesis example 49.
18g of intermediate 2-1 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 16g of B-2 was used instead of the starting material B-1. (yield 77%, MS [ M+H ]] + ＝452)
18g of intermediate 2-1, 23g of potassium carbonate, 10.7mL of perfluorobutane sulfonyl fluoride [ perfluorobutanesulfonyl floride]And a 180mL flask of Dimethylformamide (DMF) was stirred at room temperature for 1 hour. After the completion of the reaction, water was added, and the resultant solid was filtered under reduced pressure. The filtered solid was dissolved in toluene and then NH was added 4 Cl solution (aq. NH) 4 Cl), after extraction with MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (toluene/hexane), whereby 24g of intermediate 2-2 was obtained. (yield 82%, MS [ M+H)] + ＝734)
A compound E2 was produced in the same manner as in the synthesis of Compound E1 in Synthesis example 48, except that 24g of intermediate 2-2 was used in place of A2-1 and 8.8g of B-3 was used in place of B-1. (yield 75%, MS [ M+H ]] + ＝613)
Synthesis example 50.
With the exception of using 16.7g of B-4 instead of B-1, the method was carried out in accordance with Synthesis example 34The compound E1 was produced in the same manner as in the synthesis method, whereby 17g of the intermediate 2-4 was obtained. (yield 74%, MS [ M+H ] ] + ＝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%, MS [ M+H ]] + ＝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%, MS [ M+H ]] + ＝613)
Synthesis example 51.
The same procedures as in the synthesis of Compound E1 of Synthesis example 34 were repeated 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, whereby 16g of intermediate 2-6 was obtained. (yield 84%, MS [ M+H)] + ＝271)
A compound E4 was produced in the same manner as in the synthesis of Compound E1 in Synthesis 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. (yield 79%, MS [ M+H ]] + ＝536)
Synthesis example 52.
27g of E5 was obtained by the same method as the synthesis method of 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%, MS [ M+H ] ] + ＝526)
Synthesis example 53.
A2-7 was obtained as 16g of intermediate 2-7 by the same method 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. (yield 81%, MS [ M+H ]] + ＝599)
A compound E6 was produced in the same manner as in the synthesis 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%, MS [ M+H ]] + ＝741)
Synthesis example 54.
Prepared in the same manner as in the synthesis of Compound E1 of 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, 16g of intermediate 2-8 was obtained. (yield 79%, MS [ M+H ]] + ＝615)
16g of E7 was obtained by the same method as the synthesis method of Compound E1 in Synthesis example 48, except that 16g of intermediate 2-8 was used in place of A2-1 and 7.0g of B-3 was used in place of B-1. (yield 81%, MS [ M+H ]] + ＝757)
Synthesis example 55.
A preparation was carried out in the same manner as in the synthesis 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 intermediate 2-9 was obtained. (yield 74%, MS [ M+H ] ] + ＝642)
23g of intermediate 2-9 was used instead of intermediate 2-1 exceptExcept for this, 26g of intermediate 2-10 was obtained by the same method as the synthesis method of intermediate 2-2 of synthesis example 49. (yield 79%, MS [ M+H ]] + ＝924)
A compound E8 was produced in the same manner as in the synthesis 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%, MS [ M+H ]] + ＝727)
Synthesis example 56.
26g of E9 was obtained by the same method as the synthesis method of Compound E1 of Synthesis example 48 except that 26g of B-11 was used instead of B-1. (yield 84%, MS [ M+H)] + ＝603)
Synthesis example 57.
A10 (25 g) 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%, MS [ M+H ]] + ＝725)
< device example 1>
Example 1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, the detergent was a product of fei-hill (Fischer co.) and the distilled water was filtered by a filter manufactured by millbore (Millipore co.) The Filter (Filter) was used to Filter distilled water twice. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-A compound was usedIs prepared by adding the HAT compound to the composition>And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HT-A compound +.>Vacuum evaporation is performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe 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, a compound E1 and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1 to give a light-emitting layerForm an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +. >And vapor deposition is performed to form a cathode.
At the upper partIn the process, the evaporation speed of the organic matters is maintained to be 0.4 toLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 Up to 5X 10 -5 The support, thereby manufacturing the organic light emitting device. />
Examples 2 to 19 and comparative examples 1 to 7
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the dopant material of the light-emitting layer and the electron injection and transport layer material described in table 1 below were used.
For the organic light emitting devices of examples 1 to 19 and comparative examples 1 to 7 described above, the temperature was set at 10mA/cm 2 The driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm 2 The time (T95) at which the initial luminance was 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 table 1 above, it is apparent that the organic light emitting device including the compound of formula 1 or 2 of the present invention as a dopant of the light emitting layer and using the compound of formula 3 of the present invention as an electron injection and transport layer is excellent in high efficiency and/or long life characteristics.
< device example 2>
Example 20
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, the detergent was a product of fei hill company, and distilled water was filtered twice by a filter manufactured by milbo company. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-A compound was usedIs prepared by adding the HAT compound to the composition>Sequentially performing thermal vacuum evaporation to form a hole injection layer. 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, HT-B is used as followsAnd vacuum evaporation is performed to form an electron blocking layer.
Then, on the electron blocking layer, the film thickness is set to be BH-B compound (host) and compound 22 (dopant) were carried out in a weight ratio of 25:1Vacuum vapor deposition is performed to form a light-emitting layer.
Vacuum evaporating the compound E1 on the light-emitting layer to obtainForm a hole blocking layer. Vacuum vapor deposition was performed on the hole blocking layer to give +.f. of the following compound ET-E and the LiQ compound at a weight ratio of 1:1>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the process, the evaporation rate of the organic matters is maintained to be 0.4 toLithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 Up to 5X 10 -5 The support, thereby manufacturing the organic light emitting device.
Examples 21 to 38 and comparative examples 8 to 14
An organic light-emitting device was manufactured in the same manner as in example 20 above, except that the dopant material and the hole blocking layer material of the light-emitting layer were each as described in table 2 below.
For the organic light emitting devices of examples 20 to 38 and comparative examples 8 to 14 described above, the temperature was set at 10mA/cm 2 The driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm 2 The time (T95) at which the initial luminance was 95% was measured at the current density of (a), and the relative value was shown with reference to comparative example 8. The results are shown in Table 2 below.
TABLE 2
From table 2 above, it is apparent 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 using 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) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, the detergent was a product of fei hill company, and distilled water was filtered twice by a filter manufactured by milbo company. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-A compound was used Is prepared by adding the HAT compound to the composition>Sequentially performing thermal vacuum evaporation to form a hole injection layer. 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, HT-B as described below is added +.>And vacuum evaporation is performed to form an electron blocking layer. Next, on the above electron blocking layer, the film thickness is +.>The BH-C compound (host) and compound 3 (dopant) were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
Vacuum evaporating the compound E1 on the light-emitting layer to obtainForm a hole blocking layer. On the hole blocking layer, a compound E7 and the following LiQ compound were vacuum evaporated at a weight ratio of 1:1, thereby +.>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the process, the evaporation rate of the organic matters is maintained to be 0.4 toLithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 Up to 5X 10 -5 The support, thereby manufacturing the organic light emitting device. />
Examples 40 to 47 and comparative examples 15 to 17
An organic light-emitting device was manufactured in the same manner as in example 39 above, except that the dopant material, the hole-blocking layer material, and the electron injection and transport layer material 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, the temperature was set at 10mA/cm 2 The driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 15mA/cm 2 The time (T95) at which the initial luminance was 95% was measured at the current density of (a), and the relative value was shown with reference to comparative example 15. The results are shown in Table 3 below.
TABLE 3
From table 3 above, it is apparent that the organic light emitting device including the compound of formula 1 or 2 of the present invention as a dopant of the light emitting layer and using the compound of 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 (16)
1. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer provided between the first electrode and the second electrode,
Wherein the organic layers include 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 described above, a compound having the formula,
ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,
a1, A2, R1 to R3, Z1 and Z2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
n1 to n3 are each integers of 0 to 3, and when n1 to n3 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other,
p1 is either 0 or 1 and,
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
e1 to E3 are identical to or different from one another and are each independently an aromatic hydrocarbon ring,
more than 1 of R4 to R8 are represented by the following chemical formula 1-B-2, or are combined with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the others are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups 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, substituents in parentheses of 2 or more are the same or different from each other,
chemical formula 1-B-2
In the chemical formula 1-B-2,
t12 to T17 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
t18 and T21 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
T22 is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is bonded to each other with an adjacent group to form a substituted or unsubstituted ring,
t22 is an integer of 0 to 8, and when T22 is 2 or more, 2 or more T22 s are the same or different from each other
p2 is either 0 or 1 and,represents the position where the compound of formula 2 binds,
chemical formula 3
In the chemical formula 3 described above, the chemical formula,
HAr is a substituted or unsubstituted N-containing heterocyclic group,
l21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted aryl group of 2 to 4 valences, or a substituted or unsubstituted heterocyclic group of 2 to 4 valences,
ar21 is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group having a valence of 2, or-O-,
a and b are each an integer of 1 to 3,
When a is 2 or more, hars are 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 formulas 101 and 102 described above,
a1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are as defined in said formula 1,
g1 to G4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
g11 is hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group 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 are the same 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 formulas 103 to 106:
in the chemical formulas 103 to 106 described above,
r1 to R3, Z1, Z2, p1, ar1 to Ar4 and n1 to n3 are as defined in chemical formula 1,
a3, A4, and G5 to G8 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
z3, Z4, G12 and G13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined 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 each of g12 and g13 is 2 or more, substituents in brackets of 2 or more are the same 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 the chemical formula 1,
a3 and A4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group,
z1 to Z4 and Ar21 to Ar24 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined 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 formulas 201 to 203:
chemical formula 203
In the chemical formulas 201 to 203 described above,
e1 to E3, n4 to n8 are as defined in chemical formula 2,
r4 to R8, R11 and R12 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
p6 and p7 are each 1 or 2,
n5 'is an integer from 0 to 2, n 8' is an integer from 0 to 3, n11 and n12 are each an integer from 0 to 8,
when n5", n8", n11 and n12 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other.
6. The organic light-emitting device of claim 1, wherein the chemical formula 2 is represented by the following chemical formula 204:
chemical formula 204
In the chemical formula 204 described above, the chemical formula,
more than 1 of R21 to R25 are represented by the formula 1-B-2, and the others are the same or different and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a substituted or unsubstituted ring,
the definitions of E1 to E3, n4 to n8, and chemical formula 1-B-2 are the same as those in said 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 formulas 211 to 219:
chemical formula 219
In the chemical formulas 211 to 219 described above,
n4 to n8 are defined as in the chemical formula 2,
r4 to R8 and R11 to R14 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group to form a substituted or unsubstituted ring,
p6 to p9 are each 1 or 2,
n4 "and n5" are each integers from 0 to 2, n7 "and n8" are integers from 0 to 3, n11 to n14 are each integers from 0 to 8,
when n4", n5", n7", n8" and n11 to n14 are each 2 or more, substituents in 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 are combined with an adjacent group to form an aliphatic hydrocarbon ring,
more than 1 of the aliphatic hydrocarbon rings is represented by any one of the following formulas Cy1 to Cy 3:
In the formulas Cy1 to Cy3,
r31 to R40 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
r41 to R43 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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 amino group, or a substituted or unsubstituted heterocyclic group, or are combined 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, substituents in parentheses of 2 or more are the same or different from each other.
9. The organic light emitting device of claim 1, wherein-L22- (CN) of chemical formula 3 b Selected from the following structures:
in the case of the construction described above, in which the first and second support members are arranged,
l23 is a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
R51 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or 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 connected to the Ar 21.
10. 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:
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11. 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:
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。
12. the organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 3 is represented by any one of the following compounds:
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13. 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.
14. The organic light-emitting device according to claim 1, wherein the organic layer includes 2 or more light-emitting layers, and 1 layer of the 2 or more light-emitting layers contains the compound represented by the chemical formula 1 or 2.
15. 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.
16. 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 transporting layer, an electron injecting layer, and an electron injecting and transporting layer.
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| CN117327107A (en) * | 2022-06-22 | 2024-01-02 | 广东阿格蕾雅光电材料有限公司 | Organic electroluminescent material and application thereof in electroluminescent device |
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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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| KR102053324B1 (en) * | 2017-05-02 | 2019-12-06 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the 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 |
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| 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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