CN113196515B - organic light emitting device - Google Patents
organic light emitting device Download PDFInfo
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- CN113196515B CN113196515B CN202080006746.7A CN202080006746A CN113196515B CN 113196515 B CN113196515 B CN 113196515B CN 202080006746 A CN202080006746 A CN 202080006746A CN 113196515 B CN113196515 B CN 113196515B
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- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- MTHFANMIEZCVRF-UHFFFAOYSA-N spiro[fluorene-9,9'-thioxanthene]-4'-ylboronic acid Chemical compound C1=CC=C(C=2SC3=CC=CC=C3C3(C12)C1=CC=CC=C1C=1C=CC=CC13)B(O)O MTHFANMIEZCVRF-UHFFFAOYSA-N 0.000 description 1
- BEKQGJVLQFBFJD-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene]-2-ylboronic acid Chemical compound C1=CC=CC=2OC3=CC=CC=C3C3(C1=2)C1=CC=CC=C1C=1C=CC(=CC=13)B(O)O BEKQGJVLQFBFJD-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 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 relates to an organic light emitting device, including: a first electrode; a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer includes: a layer containing a compound of chemical formula 1, and a layer containing a compound of chemical formula 2.
Description
Technical Field
The present specification relates to organic light emitting devices.
The present application claims priority from korean patent application No. 10-2019-0093179, 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. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides an organic light emitting device.
Solution to the problem
The present specification provides an organic light emitting device, including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode,
the organic layer includes: a first organic layer including a compound represented by the following chemical formula 1 and a second organic layer including a compound represented by the following chemical formula 2.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
a1, A2, A3, B1 and B2 are the same or different from each other and each independently a hydrocarbon ring,
r1 to R5 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 alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, or substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3, at least one of R1 to R5 is represented by the following chemical formula 3,
[ chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
the broken line is a portion connected to A1, A2, A3, B1 or B2,
x is C or Si, and the X is C or Si,
r6 to R8 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,
n1 and n5 are each an integer of 0 to 4,
n2 and n4 are each integers from 0 to 5,
n3 is an integer of 0 to 3,
n1+n2+n3+n4+n5 is 1 or more,
when n1 to n5 are 2 or more, the substituents in brackets are the same or different from each other,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
y31 and Y32 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other to form a substituted or unsubstituted ring,
r3-1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or formula 4 below, or is combined with an adjacent group to form a hydrocarbon ring,
a31 is an integer of 0 to 8,
when a31 is plural, R3-1 are the same or different from each other,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
the above-mentioned broken line is the site of connection with the nucleus,
Ar 41 and Ar is a group 42 Are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
X 1 To X 3 Identical to or different from each other, are each independently N or CR,
X 1 to X 3 At least one of which is N,
r is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted heterocyclic group,
L 1 to L 3 Are identical or different from one another and are each independently directly bonded, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.
Effects of the invention
The organic light emitting device described in the present specification has a low driving voltage, excellent efficiency characteristics, and excellent lifetime by including the compound represented by chemical formula 1 in the first organic layer and the compound represented by chemical formula 2 in the second organic layer. In particular, the electron transport degree is adjusted by adjusting the appropriate HOMO level and LUMO level, so that low driving voltage, high efficiency, and lifetime can be improved.
Drawings
Fig. 1, 2, and 8 to 10 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 groups.
[ 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/4 pa: first 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, wherein a first organic layer including a compound represented by chemical formula 1 and a second organic layer including a compound represented by chemical formula 2 are simultaneously included. The light emitting layer including the compound of the above chemical formula 1 has a shallow HOMO level, and the compound of the above chemical formula 2 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, examples of substituents are described below, but are not limited thereto.
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 specification, a dotted line or 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, amino, 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 more than 2 substituents means that hydrogen of any substituent is substituted by other substituentsAnd (3) replacing. For example, isopropyl and phenyl groups may be linked to form Such substituents.
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 formSuch substituents. The case where 4 or more substituents are bonded is also applicable to the above description.
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 substituted with a substituent formed by joining 2 or more groups selected from the above groups, or does not have any substituent.
In the present 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 bonded with 2 or more groups selected from the above group, 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, cycloolefin (cycloolefin) is a hydrocarbon ring having a double bond, but is not an aromatic ring group, 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 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 groups. In the following structure, one of the carbons of the benzene ring may be attached at another position.
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 for the aryl group described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethylphenyloxy group, a 2,4, 6-trimethylphenoxy group, a p-tert-butylphenyloxy group, a 3-biphenylyloxy group, a 4-biphenylyloxy 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 as an arylthio group [ Aryl thio) includes phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio and the like, but is not limited thereto.
In the present specification, the silyl group may befrom-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. Examples of the boron group include, but are 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 in 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 dibenzoazasilyl groups; phenonesOxazine (phenoxazine), phenothiazine (phenothiazine), dihydrodibenzoazasilyl; spiro (dibenzosilol-dibenzoazasilyl) groups; spiro (acridine-fluorene) groups; spiro (fluorene-xanthene) based; spiro (fluorene-thioxanthene) based, and the like, but is 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 the present specification, the "five-membered or six-membered ring formed by bonding adjacent groups" means that the ring containing the substituents involved in ring formation is a five-membered or six-membered ring. It is possible to include the case where an additional ring is 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 ring and an aliphatic hydrocarbon ring, and the description of the aryl group may be applied to the aromatic hydrocarbon ring except that the aromatic hydrocarbon ring is not 1, and the description of the cycloalkyl group may be applied to the aliphatic hydrocarbon ring except that the aliphatic hydrocarbon ring is not 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 other than a 1-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 one embodiment of the present description, A1 to A3, B1 and B2 are identical to or different from each other and are each independently a monocyclic or bicyclic hydrocarbon ring.
In one embodiment of the present specification, A1 to A3, B1 and B2 are the same or different from each other, and each is independently a benzene ring or a naphthalene ring.
In one embodiment of the present specification, A1 to A3 are each a benzene ring.
In one embodiment of the present description, B1 and B2 are each a benzene ring.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1.
[ chemical formula 1-1]
In the above chemical formula 1-1, R1 to R5 and n1 to n5 are as defined in the above chemical formula 1.
In an embodiment of the present specification, R1 to R5 are the same or different from each other, each is independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, or substituted or unsubstituted heterocyclyl, or is represented by formula 3 above.
In an embodiment of the present specification, R1, R2, R4 and R5 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 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or are represented by the above chemical formula 3.
In an embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 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, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 60 carbon atoms, 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 are represented by the above chemical formula 3.
In an embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 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, a substituted or unsubstituted alkylamino group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 40 carbon atoms, 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 are represented by the above chemical formula 3.
In one embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is 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, a cyano group and an alkyl group of 1 to 10 carbon atoms or with 2 or more groups selected from the group; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.
In one embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 40 carbon atoms which is 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, a cyano group and an alkyl group of 1 to 6 carbon atoms or with 2 or more groups selected from the group; a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.
In one embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 20 carbon atoms; arylamine groups having 6 to 40 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms which is substituted with deuterium; a heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.
In one embodiment of the present description, the heterocyclic groups of R1, R2, R4 and R5 contain N as a heteroatom.
In one embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; a fluorine group; cyano group; methyl substituted or unsubstituted with deuterium; an isopropyl group; a tertiary butyl group; a cyclohexyl group; a diphenylamino group; by deuterium, fluoro, cyano, tert-butyl or CD 3 A substituted or unsubstituted phenyl group; a biphenyl group; naphthyl or pyridyl.
In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, a nitrile 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 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group, or is represented by the following chemical formula 3.
In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or is represented by the above chemical formula 3.
In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 90 carbon atoms, substituted or unsubstituted alkylamino having 1 to 20 carbon atoms, substituted or unsubstituted arylamino having 6 to 60 carbon atoms, substituted or unsubstituted heteroarylamino having 2 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclyl having 2 to 30 carbon atoms, or is represented by the above formula 3.
In one embodiment of the present specification, R3 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 1 to 18 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 60 carbon atoms, substituted or unsubstituted alkylamino having 1 to 12 carbon atoms, substituted or unsubstituted arylamino having 6 to 40 carbon atoms, substituted or unsubstituted heteroarylamino having 2 to 40 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 2 to 20 carbon atoms, or is represented by the above formula 3.
In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 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, an aryl group having 6 to 30 carbon atoms, and a silyl group, or with 2 or more substituents selected from the group consisting of the above groups; aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, halogen groups or cyano groups; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.
In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 40 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, an aryl group having 6 to 20 carbon atoms, and a silyl group, or with 2 or more substituents selected from the group consisting of the above groups; aryl groups of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, halogen groups or cyano groups; a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.
In one embodiment of the present description, R3 is hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 20 carbon atoms; an arylamine group having 6 to 40 carbon atoms which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, or a triarylamine group having 18 to 60 carbon atoms; aryl groups of 6 to 20 carbon atoms substituted or unsubstituted with deuterium, halogen groups or cyano groups; a heterocyclic group having 2 to 20 carbon atoms, or represented by the above chemical formula 3.
In one embodiment of the present description, the heterocyclyl of R3 contains N as a heteroatom.
In one embodiment of the present description, R3 is hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; a tertiary butyl group; a diphenylamino group substituted or unsubstituted with deuterium, t-butyl, trimethylsilyl or triphenylsilyl; phenyl substituted or unsubstituted with deuterium or fluoro; or a carbazolyl group.
In one embodiment of the present specification, R1, R2, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is 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, a cyano group and an alkyl group of 1 to 10 carbon atoms or with 2 or more groups selected from the group; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3,
R3 is hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 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, an aryl group having 6 to 30 carbon atoms, and a silyl group, or with 2 or more substituents selected from the group consisting of the above groups; aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, halogen groups or cyano groups; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the above chemical formula 3.
In one embodiment of the present description, one of R2 is attached in an ortho (ortho) orientation with respect to the N to which B1 is attached.
In one embodiment of the present disclosure, one of R4 is attached in an ortho oriented position relative to the N to which B2 is attached.
In one embodiment of the present description, n1 is 1 or 2.
In one embodiment of the present description, n2 is 1 to 4. In another embodiment, n2 is 1 to 3.
In one embodiment of the present description, n3 is 1 or 2.
In one embodiment of the present description, n4 is 1 to 4. In another embodiment, n4 is 1 to 3.
In one embodiment of the present description, n5 is 1.
In an embodiment of the present specification, at least one of R1 to R5 is represented by the above chemical formula 3.
In one embodiment of the present specification, one to four of R1 to R5 are represented by the above chemical formula 3.
In an embodiment of the present specification, one or two of R1 to R5 are represented by the above chemical formula 3.
In one embodiment of the present specification, one to four of R1, R2, R4 and R5 are represented by the above chemical formula 3.
In one embodiment of the present specification, one or two of R1, R2, R4 and R5 are represented by the above chemical formula 3.
In one embodiment of the present specification, R1 is represented by the above chemical formula 3.
In one embodiment of the present specification, R2 is represented by the above chemical formula 3.
In one embodiment of the present specification, R3 is represented by the above chemical formula 3.
In one embodiment of the present specification, R4 is represented by the above chemical formula 3.
In one embodiment of the present specification, R5 is represented by the above chemical formula 3.
In one embodiment of the present specification, R6 to R8 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, R6 to R8 are the same or different from each other, and are each independently 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, R6 to R8 are the same or different from each other, and each is independently an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or 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, an aryl group having 6 to 30 carbon atoms, and a silyl group, or with 2 or more groups selected from the group.
In one embodiment of the present specification, R6 to R8 are the same or different from each other, and each is independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or with 2 or more groups selected from the group.
In one embodiment of the present specification, R6 to R8 are the same or different from each other, and each is independently an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a deuterium-substituted alkyl group having 1 to 6 carbon atoms, or a trialkylsilyl group having 3 to 18 carbon atoms, or an unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R6 to R8 are the same or different from each other, each independently being methyl; a tertiary butyl group; or by deuterium, fluoro, methyl, t-butyl, CD 3 Or trimethylsilyl substituted or unsubstituted phenyl.
In one embodiment of the present description, X is C and at least one of R6 to R8 is a substituted or unsubstituted alkyl group.
In one embodiment of the present description, X is C and at least two of R6 to R8 are substituted or unsubstituted alkyl groups.
In one embodiment of the present description, X is C and at least one of R6 to R8 is a substituted or unsubstituted aryl.
In one embodiment of the present specification, X is C, R6 and R7 are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, and R8 is a substituted or unsubstituted aryl group.
In one embodiment of the present description, X is Si and at least one of R6 to R8 is a substituted or unsubstituted aryl group.
In one embodiment of the present description, X is Si and at least two of R6 to R8 are substituted or unsubstituted aryl groups.
In one embodiment of the present specification, X is C, R6 and R7 are the same or different from each other, each independently is a substituted or unsubstituted aryl group, and R8 is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, X is Si, R6 to R8 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group.
In one embodiment of the present specification, the above chemical formula 3 is represented by the following chemical formula 3-1 or 3-2.
[ chemical formula 3-1]
[ chemical formula 3-2]
In the above chemical formulas 3-1 and 3-2,
x is Si, and the X is Si,
r11 is a substituted or unsubstituted alkyl group,
r12 is a substituted or unsubstituted aryl group,
r13 to R16 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In an embodiment of the present specification, R11 to R16 may be applied to the above description of R6 to R8.
In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
In one embodiment of the present specification, R11 is an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present description, R11 is methyl.
In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R12 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, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or with 2 or more groups selected from the group.
In one embodiment of the present specification, R12 is deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a deuterium-substituted alkyl group having 1 to 6 carbon atoms, or a trialkylsilyl group having 3 to 18 carbon atoms, or an unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R12 is deuterium, fluoro, methyl, t-butyl, CD 3 Or trimethylsilyl substituted or unsubstituted phenyl.
In one embodiment of the present specification, R13 to R16 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, R13 to R16 are the same or different from each other, and are each independently 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, R13 to R16 are the same or different from each other, each independently being an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a silyl group, or with 2 or more groups selected from the group.
In one embodiment of the present specification, R13 to R16 are the same or different from each other, each independently being methyl; a tertiary butyl group; or by deuterium, fluoro, methyl, t-butyl, CD 3 Or trimethylsilyl substituted or unsubstituted phenyl.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.
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Next, chemical formula 2 is described.
In one embodiment of the present specification, Y31 and Y32 are the same or different from each other, and each is independently hydrogen, 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 bonded to each other to form a ring.
In one embodiment of the present specification, Y31 and Y32 are the same or different from each other, and each is independently hydrogen, 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 each other to form an aliphatic ring.
In one embodiment of the present specification, Y31 and Y32 are the same or different from each other, and each is independently hydrogen, 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 each other to form an aliphatic ring having 3 to 10 carbon atoms.
In one embodiment of the present specification, Y31 and Y32 are bonded to each other to form an aliphatic ring having 3 to 6 carbon atoms.
In one embodiment of the present specification, the above Y31 and Y32 are bonded to each other to form a cyclopentyl ring.
In one embodiment of the present specification, Y31 and Y32 are bonded to each other to form a ring in which an aliphatic ring having 3 to 10 carbon atoms and an aromatic ring are condensed.
In one embodiment of the present specification, Y31 and Y32 are combined with each other to form a ring in which a cyclopentyl ring and a benzene ring are condensed.
In one embodiment of the present specification, Y31 and Y32 are the same or different from each other, and each is independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, the above Y31 and Y32 are the same or different from each other and are each independently hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, terphenyl, phenanthryl or anthracyl,
the above-mentioned phenyl group, biphenyl group, naphthyl group, terphenyl group, phenanthryl group or anthracyl group is substituted or unsubstituted with methyl group, ethyl group, isopropyl group, t-butyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, phenanthryl group or anthracyl group.
In an embodiment of the present specification, Y31 and Y32 are the same or different from each other, and each is independently hydrogen, methyl, phenyl, naphthyl, phenyl substituted with methyl, naphthyl substituted with methyl, phenyl substituted with naphthyl, naphthyl substituted with phenyl, or an aliphatic ring having 3 to 6 carbon atoms is formed by bonding with each other.
In one embodiment of the present specification, R3-1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or formula 4, or is combined with an adjacent group to form a hydrocarbon ring.
In one embodiment of the present specification, R3-1 is hydrogen, deuterium, alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or formula 4, or is bonded to each other with an adjacent group to form a hydrocarbon ring having 3 to 20 carbon atoms.
In one embodiment of the present specification, R3-1 is hydrogen, methyl, t-butyl, phenyl substituted with methyl, biphenyl, naphthyl, or formula 4, or an aromatic hydrocarbon ring having 6 to 20 carbon atoms is formed by bonding adjacent groups to each other.
In one embodiment of the present specification, R3-1 is hydrogen, methyl, t-butyl, phenyl, naphthyl, or formula 4, or is bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
In one embodiment of the present specification, R3-1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, a31 is an integer of 1 to 8, and one or more R3-1 is formula 4.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other, is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Identical to or different from each other, are each independently a substituted or unsubstituted carbonAryl groups having 6 to 30 atoms, or substituted or unsubstituted heterocyclic groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Are identical or different from one another and are each independently substituted or unsubstituted aryl radicals having 6 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other and is independently methyl, ethyl, butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylenyl, fluorenyl, carbazolyl, benzocarbazolyl, indenocarbazolyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoneOxazinyl, phenothiazinyl, pheno ∈>A thienyl group (phenyloxathin), a trimethylsilyl group,
the above phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylene, fluorenyl, carbazolyl, benzocarbazolyl, indenocarzolyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoneOxazinyl, phenothiazinyl, pheno ∈>The thienyl group is substituted or unsubstituted with any one or more selected from deuterium, CN, methyl, t-butyl, phenyl substituted with methyl, trifluoromethyl, trifluoromethoxy, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, and carbazolyl.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other and is independently phenyl, biphenyl, terphenyl, naphthyl or phenanthryl, the phenyl, biphenyl, terphenyl, naphthyl or phenanthryl being substituted or unsubstituted by deuterium, CN, alkyl, aryl, silyl or heteroaryl.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other and is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or a phenanthryl group, and the phenyl group, the biphenyl group, the terphenyl group, the naphthyl group or the phenanthryl group is substituted or unsubstituted with deuterium, CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other and is independently phenyl, biphenyl, terphenyl, naphthyl or phenanthryl, and any one or more of the above phenyl, biphenyl, terphenyl, naphthyl or phenanthryl groups are substituted or unsubstituted with deuterium, CN, methyl, ethyl, butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, perylenyl, triphenylenyl, pyrenyl, fluoranthenyl, thienyl, furyl, pyridyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothienyl.
In one embodiment of the present specification, the above X 1 To X 3 Is N.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 1 N, the remainder being CR.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 2 N, the remainder being CR.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 3 N, the remainder being CR.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 1 Is CR (CR)The balance being N.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 2 CR, and N for the rest.
In one embodiment of the present specification, the above X 1 To X 3 X in (2) 3 CR, and N for the rest.
In one embodiment of the present specification, R is hydrogen, deuterium, a halogen group, a nitrile 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 cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R is hydrogen, deuterium, nitrile group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R is hydrogen, deuterium or nitrile group.
In one embodiment of the present specification, R is hydrogen.
In one embodiment of the present specification, the chemical formula 2 is represented by the following chemical formula 2-1.
[ chemical formula 2-1]
In the above chemical formula 2-1,
y is CR111R112, O or S,
r111, R112, R3-2 and R3-3 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, a substituted or unsubstituted heteroaryl group, or the above chemical formula 4, or are combined with each other with adjacent groups to form a hydrocarbon ring,
l31 and L32 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
a33 is an integer of 0 to 8,
b33 is an integer of 0 to 8,
a33 and b33 are plural, the substituents in parentheses are the same or different from each other,
n33 is 0 or 1 and is preferably selected from the group consisting of,
when n33 is 0, hydrogen is bonded to each of the 2 benzene rings bonded to Y.
In one embodiment of the present specification, a33 is 0. When a33 is 0, the position which can be substituted with R3-2 is substituted with hydrogen.
In one embodiment of the present disclosure, b33 is 0. When b33 is 0, the position which can be substituted with R3-3 is substituted with hydrogen.
In one embodiment of the present specification, Y is O or S.
In one embodiment of the present specification, R3-2 is hydrogen.
In one embodiment of the present specification, R3-3 is hydrogen.
In one embodiment of the present specification, a33 is 1.
In one embodiment of the present specification, b33 is 1.
In one embodiment of the present specification, R3-2 is represented by the following chemical formula 6 or 7.
In one embodiment of the present specification, R3-3 is represented by the following chemical formula 6 or 7.
[ chemical formula 6]
[ chemical formula 7]
In the above-mentioned chemical formulas 6 and 7,
the above-mentioned broken line is the site of connection with the nucleus,
l4 and L5 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
ar5 and Ar6 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
c and d are integers of 0 to 5,
when c and d are plural, the substituents in brackets are the same or different from each other.
In one embodiment of the present specification, R3-2 and R3-3 are the same or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, chemical formula 4, chemical formula 6 or chemical formula 7.
In one embodiment of the present specification, R3-2 and R3-3 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, formula 4, formula 6 or formula 7.
In one embodiment of the present specification, the substituent other than the above formula 4, the above formula 6 or the above formula 7 in the above R3-2 and R3-3 is methyl, t-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene, the above phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene is substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.
In one embodiment of the present specification, a33 is 2, and R3-2 are the same or different from each other.
In one embodiment of the present specification, b33 is 2, and R3-3 are the same or different from each other.
In one embodiment of the present specification, the substituent of the plurality of R3-2 other than the above formula 4, the above formula 6 or the above formula 7 is methyl, t-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene, the above phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene being substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.
In one embodiment of the present specification, the substituent of the plurality of R3-3 other than the above formula 4, the above formula 6 or the above formula 7 is methyl, t-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene, the above phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinazolinyl, quinolinyl, quinoxalinyl, triphenylene being substituted or unsubstituted with any one or more substituents selected from deuterium, CN, alkyl, aryl and heteroaryl.
In one embodiment of the present specification, the L 1 To L 5 Are identical or different from one another and are each independently directly bonded, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.
In one embodiment of the present specification, the L 1 To L 5 Are identical or different from one another and are each independently directly bonded, substituted or unsubstituted arylene having 6 to 30 carbon atoms or substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 To L 5 Are identical or different from one another and are each independently of one another directly bonded, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiophene Oxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>A thia group, a 2-valent dibenzothiazyl group, a 2-valent pyrrolyl group, a 2-valent furanyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, or a 2-valent triazinyl group,
the phenylene group, the 2-valent biphenyl group, the 2-valent terphenyl group, the 2-valent fluorenyl group and the 2-valent phenoneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>A thienyl group, a 2-valent dibenzosilol group, a 2-valent pyrrolyl group, a 2-valent furyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, or a 2-valent triazinyl group may be substituted or unsubstituted with CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 To L 5 Are identical or different from one another and are each independently of one another directly bonded, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiopheneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>Thienyl, 2-valent dibenzosilol, 2-valent pyrrolyl, 2-valent furyl, 2-valent thienyl, 2-valent pyridineA group, a pyrimidinyl group of valence 2, or a triazinyl group of valence 2,
the phenylene group, the 2-valent biphenyl group, the 2-valent terphenyl group, the 2-valent fluorenyl group and the 2-valent phenoneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>The thienyl, 2-valent dibenzosilol, 2-valent pyrrolyl, 2-valent furyl, 2-valent thienyl, 2-valent pyridyl, 2-valent pyrimidinyl, or 2-valent triazinyl may be substituted or unsubstituted with CN, methyl, butyl, tert-butyl, phenyl, naphthyl, biphenyl, or terphenyl.
In one embodiment of the present specification, the L 1 To L 5 Are identical or different from one another and are each independently of one another directly bonded, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiopheneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>A thia group, 2-valent dibenzothiazyl group, 2-valent pyrrolyl group, 2-valent furyl group, 2-valent thienyl group, 2-valent pyridyl group, 2-valent pyrimidinyl group, or 2-valent triazinyl group, wherein the phenylene group, 2-valent biphenyl group, 2-valent terphenyl group, 2-valent fluorenyl group, 2-valent phenone>Oxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>The thia group, 2-valent dibenzothiazyl group, 2-valent pyrrolyl group, 2-valent furyl group, 2-valent thienyl group, 2-valent pyridyl group, 2-valent pyrimidinyl group, or 2-valent triazinyl group may overlap with any of 2 or more thereof >Is present within the compound.
In the present specification, the overlapping structure means that 2 or more substituents are sequentially bonded. For example, "phenylene overlaps with a carbazolyl group of valence 2" means that the carbazolyl groups of valence-2 are combined in sequence.
In one embodiment of the present specification, the L 1 To L 3 Are identical or different from one another and are each independently of one another a direct bond, an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 To L 3 Is a direct bond.
In one embodiment of the present specification, the L 1 To L 3 Each of which is the same or different from the other, is independently a direct bond, phenylene, biphenyl of 2 valences, terphenyl of 2 valences, naphthyl of 2 valences, quinazolinyl of 2 valences, quinolinyl of 2 valences, quinoxalinyl of 2 valences, dibenzofuranyl of 2 valences, dibenzothienyl of 2 valences, carbazolyl of 2 valences, dibenzosilol of 2 valences, pyrrolyl of 2 valences, furanyl of 2 valences, thienyl of 2 valences, or pyridyl of 2 valences.
In one embodiment of the present specification, the L 3 For direct bonding, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinoline A group, a quinoxalinyl group of valence 2, a dibenzofuranyl group of valence 2, a dibenzothienyl group of valence 2, a carbazolyl group of valence 2, a dibenzosilol group of valence 2, a pyrrolyl group of valence 2, a furyl group of valence 2, a thienyl group of valence 2, or a pyridyl group of valence 2.
In one embodiment of the present specification, the L 3 Is a direct bond or phenylene.
In one embodiment of the present specification, the above-mentioned L31 and L32 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
In one embodiment of the present specification, L31 and L32 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
In one embodiment of the present specification, the above L31 and L32 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiopheneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl >A thia group, a 2-valent dibenzothiazyl group, a 2-valent pyrrolyl group, a 2-valent furanyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, or a 2-valent triazinyl group,
the phenylene group, the 2-valent biphenyl group, the 2-valent terphenyl group, the 2-valent fluorenyl group and the 2-valent phenoneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinylDibenzofuranyl of valence 2, dibenzothiophenyl of valence 2, carbazolyl of valence 2, benzocarbazolyl of valence 2, indenocarbazolyl of valence 2, phenothiazinyl of valence 2, pheno->A thienyl group, a 2-valent dibenzosilol group, a 2-valent pyrrolyl group, a 2-valent furyl group, a 2-valent thienyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, or a 2-valent triazinyl group may be substituted or unsubstituted with CN, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, the above L31 and L32 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent fluorenyl, 2-valent thiopheneOxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl >A thia group, 2-valent dibenzothiazyl group, 2-valent pyrrolyl group, 2-valent furyl group, 2-valent thienyl group, 2-valent pyridyl group, 2-valent pyrimidinyl group, or 2-valent triazinyl group, wherein the phenylene group, 2-valent biphenyl group, 2-valent terphenyl group, 2-valent fluorenyl group, 2-valent phenone>Oxazinyl, 2-valent naphthyl, 2-valent quinazolinyl, 2-valent quinolinyl, 2-valent quinoxalinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent carbazolyl, 2-valent benzocarbazolyl, 2-valent indenocarbazolyl, 2-valent phenothiazinyl, 2-valent phenoxazinyl>The thia group, 2-valent dibenzothiazyl group, 2-valent pyrrolyl group, 2-valent furanyl group, 2-valent thienyl group, 2-valent pyridyl group, 2-valent pyrimidinyl group, or 2-valent triazinyl group may exist in any of the above-mentioned structures overlapping with each other in the compound.
In one embodiment of the present specification, R3-2 and the adjacent group are bonded to each other to form a hydrocarbon ring.
In one embodiment of the present specification, R3-2 and the adjacent group are bonded to each other to form an aromatic hydrocarbon ring.
In one embodiment of the present specification, R3-2 and the adjacent group are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
In one embodiment of the present specification, R3-3 and the adjacent group are bonded to each other to form a hydrocarbon ring.
In one embodiment of the present specification, R3-3 and the adjacent group are bonded to each other to form an aromatic hydrocarbon ring.
In one embodiment of the present specification, R3-3 and the adjacent group are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
In one embodiment of the present specification, the above chemical formula 2-1 is represented by any one of the following chemical formulas 2-2 to 2-5.
[ chemical formula 2-2]
[ chemical formulas 2-3]
/>
[ chemical formulas 2-4]
[ chemical formulas 2-5]
In the above chemical formulas 2-2 to 2-5, R3-2, L32 and a33 are as defined in the above chemical formula 2-1,
r3-4 and R3-5 are the same as R3-3 of the above chemical formula 2-1,
a34 and a35 are the same as a33 of the above chemical formula 2-1.
In one embodiment of the present specification, when n33 is 0, one of the substituents other than the substituent of formula 4, among the R3-2 and R3-3, is a substituted or unsubstituted aryl group.
In one embodiment of the present specification, when n33 is 0, one of the substituents other than the substituent of formula 4, among the R3-2 and R3-3, is a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted benzofluorenyl group.
In one embodiment of the present specification, when n33 is 0, one of the substituents other than the substituent of formula 4, among R3-2 and R3-3, is a fluorenyl group substituted or unsubstituted with deuterium, alkyl or alkylaryl; or a benzofluorenyl group substituted or unsubstituted with deuterium, alkyl, or alkylaryl groups.
In one embodiment of the present specification, R3-4 and R3-5 are hydrogen.
In one embodiment of the present specification, a34 and a35 are 0.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Are the same or different from each other and are each independently methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or polycyclic heteroaryl groups containing Si, N, O or S,
the methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a polycyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Are the same or different from each other and are each independently methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or polycyclic heteroaryl groups containing Si, N, O or S,
the methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a polycyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with one or more substituents selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzocarbazolyl group, and a substituted or unsubstituted pyridyl group.
In one embodiment of the present specification, ar5 and Ar6 mentioned above are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, ar5 and Ar6 are the same or different from each other, and each is independently methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or polycyclic heteroaryl groups containing Si, N, O or S,
the methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a polycyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group of 10 carbon atoms of 1, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 20 carbon atoms.
In one embodiment of the present specification, ar5 and Ar6 are the same or different from each other, and each is independently methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or polycyclic heteroaryl groups containing Si, N, O or S,
the methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a polycyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with one or more substituents selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzocarbazolyl group, and a substituted or unsubstituted pyridyl group.
In one embodiment of the present specification, ar5 and Ar6 are the same or different from each other, and each is independently methyl; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a tricyclic heteroaryl group containing Si, N, O or S,
the methyl group; a silyl group; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; dibenzofuranyl; dibenzothienyl; carbazolyl; a silol group; or a tricyclic heteroaryl group containing Si, N, O or S is substituted or unsubstituted with one or more substituents selected from deuterium, nitrile, halogen, methyl, trifluoromethyl, trifluoromethoxy, methoxy, trimethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl substituted with phenyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, indolocarbazolyl, pyridyl.
In one embodiment of the present specification, ar is as described above 41 And Ar is a group 42 Each of which is the same or different from the other and is independently methyl, ethyl, butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylenyl, fluorenyl, carbazolyl, benzocarbazolyl, indenocarbazolyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, phenone Oxazinyl, 2-valent phenothiazinyl, 2-valent pheno +.>A thienyl group, or a trimethylsilyl group,
phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, perylene, fluorenyl, fluorenxanthenyl, carbazolyl, benzocarbazolyl, indenocarbazolyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoneOxazinyl, phenothiazinyl of valence 2, or pheno +.2->The thienyl group is substituted or unsubstituted with any one or more selected from the group consisting of deuterium, CN, methyl, t-butyl, phenyl substituted with methyl, trifluoromethyl, trifluoromethoxy, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, and carbazolyl.
In one embodiment of the present specification, the chemical formula 2 is any one of the following compounds.
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In one embodiment of the present specification, the chemical formula 2 is any one of the compounds described in the following table. In the following table, the dotted line is a position bonded to chemical formula 4.
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According to an embodiment of the present application, the compound of formula 1 may be manufactured as shown in the following reaction formula 1, and the compound of formula 2 may be manufactured as shown in the following reaction formula 2. The following equations 1 and 2 describe a synthesis process of a part of the compounds corresponding to the equations 1 and 2 of the present application, but various compounds corresponding to the equations 1 and 2 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 numbers of substituents may be changed according to a technique known in the art.
[ reaction type 1]
[ reaction type 2]
In the above reaction formula 1, R represents a substituent attached to the nucleus, R1 and R5, B1 or B2 may be the present application, and the remaining substituents are defined as above. In the above reaction scheme 2, the substituents are defined as above, and the synthesis can be performed by a general coupling reaction. For example, the compound can be produced by using a suzuki coupling reaction or the like.
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 the above chemical formula 1 and the second organic layer is formed using the compound represented by the above chemical formula 2.
The first organic layer containing the compound represented by the above chemical formula 1 and the second organic layer containing the compound represented by the above chemical formula 2 may be formed not only by a vacuum vapor deposition 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 composed of a structure including only the first organic layer and the second organic layer described above, but may also be composed of a structure further including an additional organic layer. The additional organic layer may be 1 or more layers of a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, 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 disposed 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 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 above chemical formula 1 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 the compound represented by the chemical formula 1.
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 is blue, and the light emitting layer including no compound represented by the above chemical formula 1 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 includes a fluorescent dopant, and the light emitting layer including no compound represented by the above chemical formula 1 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 is 400nm to 500nm. That is, the light emitting layer including the compound represented by the above chemical formula 1 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.
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 this case, the hole blocking layer is provided in contact with the light emitting layer, and the electron injection and transport layer is provided in contact with the cathode.
In one embodiment of the present disclosure, the second organic layer is disposed 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 an 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 balance of holes and electrons in the light emitting layer is maximized by adjusting the electron mobility of the electron transporting layer, the proportion of the organic alkali metal compound or the organic alkaline earth metal compound, so that the light emitting efficiency can be increased.
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 included in 2:8 to 8:2, and more preferably, may be included 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 be an organic light emitting device having 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 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 2 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 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 2 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 described above, the compound represented by the above chemical formula 1 may be contained in the light emitting layers 6RP, 6GP, 6BF, and the compound represented by the above chemical formula 2 may be contained in 1 or more layers among the first electron transporting layer 9a, the second electron transporting layer 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 in a form in which the respective organic light emitting devices are bonded 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 1 or more charge generation layers provided 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 closer to the anode than the P-type charge generation layer, and the P-type charge generation layer means a charge generation layer 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 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 2 may be contained in the first electron transporting layer 9a or the electron injecting and transporting layer 8.
Organic light emitting devices including the above-described first to third stacks are illustrated in fig. 4 to 7.
Fig. 4 illustrates 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 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 2 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 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 2 may be contained in 1 or more layers among the first electron transporting layer 9a, the second electron transporting layer 9b, the third electron transporting layer 9c, and the electron injecting 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 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 2 may be contained in 1 or more layers among the first electron transporting layer 9a, the second electron transporting layer 9b, the third electron transporting layer 9c, and the electron injecting 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 may be contained in 1 or more layers among the first, second, and third blue fluorescent light-emitting layers 6BFa, 6BFb, and 6BFc, and the compound represented by the above chemical formula 2 may be contained in 1 or more layers among the first, second, third, and electron injection layers 9a, 9b, 9 c.
Fig. 9 illustrates an organic light-emitting device structure 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, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 are stacked in this order. 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 2 may be contained in the hole blocking layer 7 or the electron injection and transport layer 8.
Fig. 10 illustrates an organic light-emitting device structure in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are stacked in this order. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the light emitting layer 6, and the compound represented by the above chemical formula 2 may be contained in the electron injection and transport layer 8.
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 cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance 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 receive 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 is a 2-layer structure, and each layer contains the same or different substances from each other. In one embodiment of the present invention, an arylamine group compound is used as the substance of the hole transporting layer.
As the above-mentioned hole injection and transport layer, as a layer for simultaneously carrying out hole transport and hole injection, a hole transport layer material and/or a hole injection layer material known in the art may be used.
As the above-mentioned electron injection and transport layer, as a layer for simultaneously carrying out electron transport and electron injection, an electron transport layer material and/or an electron injection layer material known in the art may be used.
An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may 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 derivatives, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., 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 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but 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 material is a material capable of favorably receiving electrons from the cathode and transferring them to the light-emitting layer, and has mobility to electronsLarge substances are suitable. 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 can perform a function of smoothly injecting electrons. 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,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
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.
Preparation example 1 Synthesis of Compound 1
1) Synthesis of intermediate 1
100g of 1-bromo-2,3-dichloro-5-methylbenzene [ 1-bromoo-2, 3-dichloro-5-methylparaben under a nitrogen atmosphere]117g of amine A-1, 60g of sodium tert-butoxide, 2.1g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)) 3 ) 2 ) After addition to 3.0L of toluene, the mixture was heated and stirred at 120℃for 2 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (toluene/hexane) to obtain 130g of intermediate 1 (yield 82%, mass) [ M+]＝441)。
2) Synthesis of intermediate 2
30g of intermediate 1, 28g of Compound A-2, 9.8g of sodium tert-butoxide, 0.7g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)) were combined under a nitrogen atmosphere 3 ) 2 ) After addition to 550mL of toluene, the mixture was heated and stirred at 150℃for 8 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 42g of intermediate 2 (yield 76%, mass [ M+) ]＝810)。
3) Synthesis of Compound 1
To a flask containing 42g of intermediate 2 dissolved in 400mL of toluene (anhydrous) cooled to 0deg.C under nitrogen atmosphere was slowly added dropwise 122mL of t-butyllithium (t-BuLi (1.7M in pentane)), followed by stirring at 60deg.C for 3 hours. At the end of the lithium-halogen exchange reaction, the mixture was cooled again to 0℃and 7.5mL of boron tribromide (BBr) was slowly added dropwise 3 ) Then, the temperature was raised to 70℃and stirred for 10 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.5g of Compound 1 (yield 23%, mass [ M+)]＝783)。
PREPARATION EXAMPLE 2 Synthesis of Compound 2
1) Synthesis of intermediate 3
20g of 2-bromo-1,3-diiodo-5-methylbenzene [2-bromo-1, 3-diodo-5-methylparaben under a nitrogen atmosphere]38g of amine A-2, 14g of sodium tert-butoxide, 0.24g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu) 3 ) 2 ) After addition to 450mL of toluene, the mixture was heated and stirred at 120℃for 4 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 35g of intermediate 3 (yield 76%, mass [ M+) ]＝979)。
2) Synthesis of Compound 2
Under nitrogen atmosphere, 35g of the mixture was dissolved in 300mL of water and cooled to 0 DEG C35mL of n-butyllithium (n-BuLi (2.5M in hexane)) was slowly added dropwise to the flask of toluene (anhydrous) intermediate 3, followed by stirring at 60℃for 1 hour. At the end of the lithium-halogen exchange reaction, the mixture was cooled again to 0℃and 5.2mL of boron tribromide (BBr) was slowly added dropwise 3 ) Then, the temperature was raised to 70℃and stirred for 6 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.0g of Compound 2 (yield 34%, mass [ M+)]＝908)。
PREPARATION EXAMPLE 3 Synthesis of Compound 3
1) Synthesis of intermediates 4 and 5
18g of intermediate 4 was obtained (yield 75% by mass [ m+ ] =579) by the same method as that for producing intermediate 1 of production example 1, except that 18g of amine a-3 was used instead of amine a-1.
Further, 18g of intermediate 5 was obtained (yield 70%, mass [ m+ ] =824) by the same method as that of the production method of intermediate 2 of production example 1, except that 18g of intermediate 4 was used instead of intermediate 1 and 8.8g of amine a-1 was used instead of amine a-2.
2) Synthesis of Compound 3
The production was performed in the same manner as the production method of compound 1 of production example 1, except that 18g of intermediate 5 was used instead of intermediate 2, whereby 4.0g of compound 3 was obtained (yield 23%, mass [ m+ ] =797).
PREPARATION EXAMPLE 4 Synthesis of Compound 4
14.5g of intermediate 6 was obtained (yield 78%, mass [ m+ ] =824) by performing the same method as the production method of intermediate 2 of production example 1, except that 9.5g of amine a-4 was used instead of amine a-2.
3.1g of compound 4 was obtained (yield 22%, mass [ m+ ] =797) by the same method as the production method of compound 1 of production example 1, except that 14.5g of intermediate 6 was used instead of intermediate 2.
PREPARATION EXAMPLE 5 Synthesis of Compound 5
1) Synthesis of intermediate 7
The amination reaction was performed in the same manner as the production method of intermediate 1 of production example 1, except that 20g of 3-bromo-4,5-dichlorophenol [ 3-bromoo-4, 5-dichlorophenol ] was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene, and then the following reaction was performed without a purification process.
After the amination reaction product was dissolved in 420mL of Dimethylformamide (DMF), 34g of potassium carbonate (potassium carbonate) was added at room temperature, and 22mL of perfluorobutylsulfonyl fluoride [ perfluorobutanesulfonyl floride ] was added dropwise at 0 ℃ ]. After the completion of the reaction, 400mL of water and 200mL of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was washed 2 times with NaCl solution (aq.nacl). Recovering the separated organic layer with Mg 2 SO 4 (anhydrous) treatment and filtration. The solvent of the filtered solution was distilled off under reduced pressure, and purification was performed by recrystallization (ethyl acetate/hexane) to obtain 40g of intermediate 7 (yield 77%, mass [ M+]＝725)。
2) Synthesis of intermediate 8
20g of intermediate 7, 4.7g of amine A-5, 0.16g of bis (dibenzylideneacetone) Palladium (0) [ Palladium (0) bis (dibenzylideneacetone) were charged](Pd(dba) 2 ) A flask of 0.26g of 2-dicyclohexylphosphorus-2 ',4',6'-triisopropylbiphenyl (2-Dicyclohexylphosphino-2', 4',6' -triisopropylphenyl) (Xphos), 18g of cesium carbonate (process carbonate) and 300mL of xylene was heated and stirred at 130℃for 12 hours. The reaction solution was cooled to room temperature, and NH was added 4 Cl saturated solution (sat. Aq. NH) 4 Cl) and xylene, and after separating the liquid, the solvent was distilled off under reduced pressure. Purification by column chromatography (ethyl acetate/hexane) gave 13g of intermediate 8 (yield 77%, mass [ M+]＝594)。
3) Synthesis of intermediate 9
Except that 13g of intermediate 8 was used instead of intermediate 1, the same procedure as in production example 1 was followed to obtain 17g of intermediate 9 (yield 81%, mass [ m+ ] =963).
4) Synthesis of Compound 5
3.5g of compound 5 (yield 21%, mass [ m+ ] =937) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 17g of the intermediate 9 was used instead of the intermediate 2.
PREPARATION EXAMPLE 6 Synthesis of Compound 6
Except that 11g of amine a-6 was used instead of amine a-2, the production was performed in the same manner as the production method of intermediate 2 of production example 1, whereby 15g of intermediate 10 was obtained (yield 75%, mass [ m+ ] =886).
3.0g of compound 6 (yield 21%, mass [ m+ ] =860) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 15g of the intermediate 10 was used instead of the intermediate 2.
PREPARATION EXAMPLE 7 Synthesis of Compound 7
Except that 9.7g of a-7 was used instead of the amine a-2, the production was performed in the same manner as the production method of the intermediate 2 of production example 1, whereby 13g of the intermediate 11 was obtained (yield 69%, mass [ m+ ] =830).
3.0g of compound 7 was obtained (yield 24%, mass [ m+ ] =804) by the same method as the production method of compound 1 of production example 1, except that 5.0g of intermediate 11 was used instead of intermediate 2.
PREPARATION EXAMPLE 8 Synthesis of Compound 8
Except that 14g of a-8 was used instead of the amine a-2, the production was performed in the same manner as the production method of the intermediate 2 of production example 1, whereby 20g of the intermediate 12 was obtained (yield 72%, mass [ m+ ] =820).
4.2g of compound 8 (yield 22%, mass [ m+ ] =792) was obtained by producing the compound by the same method as the production method of compound 1 of production example 1, except that 20g of intermediate 12 was used instead of intermediate 2.
PREPARATION EXAMPLE 9 Synthesis of Compound 9
Except that 14g of a-9 was used instead of the amine a-5, the production was performed in the same manner as the production method of intermediate 8 of production example 5, whereby 16g of intermediate 13 was obtained (yield 68%, mass [ m+ ] =853).
18g of intermediate 14 was obtained (yield 78%, mass [ m+ ] =1222) by performing the same method as the method for producing intermediate 2 of production example 1, except that 16g of intermediate 13 was used instead of intermediate 1.
3.6g of compound 9 (yield 20%, mass [ m+ ] =1195) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 18g of the intermediate 14 was used instead of the intermediate 2.
Preparation example 10 Synthesis of Compound 10
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The production was performed in the same manner as the production method of intermediate 2 in production example 1, except that 28g of a-10 was used instead of the amine a-2, whereby 43g of intermediate 15 was obtained (yield 77%, mass [ m+ ] =824).
Except that 43g of intermediate 15 was used instead of intermediate 2, the production was performed in the same manner as in production example 1, whereby 8.9g of compound 10 was obtained (yield 21%, mass [ m+ ] =797).
PREPARATION EXAMPLE 11 Synthesis of Compound 11
Except that 29g of a-11 was used instead of the amine a-2, the production was performed in the same manner as the production method of the intermediate 2 of production example 1, whereby 41g of the intermediate 16 was obtained (yield 72%, mass [ m+ ] =834).
Except that 41g of intermediate 16 was used instead of intermediate 2, the production was performed in the same manner as in production example 1, whereby 6.7g of compound 11 was obtained (yield 17%, mass [ m+ ] =807).
PREPARATION EXAMPLE 12 Synthesis of Compound 12
18g of intermediate 17 (yield 76%, mass [ m+ ] =565) was obtained by producing the same method as that for producing intermediate 1 of production example 1, except that 17g of a-2 was used instead of the amine a-1.
The production was performed in the same manner as the production method of intermediate 2 in production example 1, except that 18g of intermediate 17 was used instead of intermediate 1 and 17g of a-12 was used instead of amine a-2, whereby 24g of intermediate 18 was obtained (yield 72%, mass [ m+ ] =1046).
Except that 24g of intermediate 18 was used instead of intermediate 2, the production was performed in the same manner as the production method of compound 1 of production example 1, whereby 5.1g of compound 12 was obtained (yield 22%, mass [ m+ ] =1020).
PREPARATION EXAMPLE 13 Synthesis of Compound 13
The production was performed in the same manner as in production example 1 except that 5.0g of 1-bromo-2, 3-dichloro-5- (methyl-d 3) -benzene was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene, whereby 13g of intermediate 19 was obtained (yield 71%, mass [ m+ ] =444).
The production was performed in the same manner as in production example 1. Production of intermediate 2, except that 13g of intermediate 19 was used instead of intermediate 1 and 8.8g of a-13 was used instead of amine a-2, to obtain 14g of intermediate 20 (yield 67%, mass [ m+ ] =709).
3.4g of compound 13 was obtained (yield 25%, mass [ m+ ] =682) by the same method as the production method of compound 1 of production example 1, except that 14g of intermediate 20 was used instead of intermediate 2.
PREPARATION EXAMPLE 14 Synthesis of Compound 14
Except that 6.2g of a-14 was used instead of the amine a-5, the production was performed in the same manner as in the production method of intermediate 8 of production example 5, whereby 13g of intermediate 21 was obtained (yield 72%, mass [ m+ ] =650).
18g of intermediate 22 was obtained (yield 77%, mass [ m+ ] =1172) by the same method as the production method of intermediate 2 of production example 1, except that 16g of intermediate 21 was used instead of intermediate 1 and 11g of a-15 was used instead of amine a-2.
4.0g of compound 14 (yield 23%, mass [ m+ ] =1145) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 18g of the intermediate 22 was used instead of the intermediate 2.
PREPARATION EXAMPLE 15 Synthesis of Compound 15
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14g of intermediate 23 (yield 73%, mass [ m+ ] =840) was obtained by producing the same method as that of producing intermediate 2 of production example 1, except that 9.9g of a-16 was used instead of the amine a-2.
2.7g of compound 15 (yield 20%, mass [ m+ ] =814) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 14g of the intermediate 23 was used instead of the intermediate 2.
PREPARATION EXAMPLE 16 Synthesis of Compound 16
Except that 13.3g of a-17 was used instead of the amine a-2, the production was performed in the same manner as the production method of the intermediate 2 of production example 1, whereby 15g of the intermediate 24 was obtained (yield 67%, mass [ m+ ] =989).
3.0g of compound 16 (yield 21%, mass [ m+ ] =963) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 15g of the intermediate 24 was used instead of the intermediate 2.
Preparation example 17 Synthesis of Compound 17
The production was performed in the same manner as in production example 1. Production of intermediate 2, except that 17.1g of a-18 was used instead of the amine a-2, whereby 20g of intermediate 25 was obtained (yield 65%, mass [ m+ ] =908).
4.1g of compound 17 (yield 21%, mass [ m+ ] =882) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 20g of the intermediate 25 was used instead of the intermediate 2.
PREPARATION EXAMPLE 18 Synthesis of Compound 18
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14g of intermediate 26 was obtained (yield 66%, mass [ m+ ] =938) by producing the same method as that for producing intermediate 2 of production example 1, except that 12g of a-19 was used instead of the amine a-2.
2.9g of compound 18 (yield 21%, mass [ m+ ] =912) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 14g of the intermediate 26 was used instead of the intermediate 2.
PREPARATION EXAMPLE 19 Synthesis of Compound 19
The production was performed in the same manner as the production method of intermediate 20 of production example 13, except that 17g of a-20 was used instead of amine a-13, whereby 19g of intermediate 27 was obtained (yield 62%, mass [ m+ ] =911).
3.6g of compound 19 (yield 20%, mass [ m+ ] =885) was obtained by producing the compound by the same method as the production method of the compound 13 of production example 13, except that 19g of the intermediate 27 was used instead of the intermediate 20.
PREPARATION EXAMPLE 20 Synthesis of Compound 20
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The production was performed in the same manner as in production example 1 except that 10g of 1-bromo-2, 3-dichloro-5-tert-butylbenzene was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene, whereby 13g of intermediate 28 was obtained (yield 76%, mass [ m+ ] =483).
18g of intermediate 29 was obtained (yield 70%, mass [ m+ ] =950) by the same method as the production method of intermediate 2 of production example 1, except that 13g of intermediate 28 was used instead of intermediate 1 and 14g of a-18 was used instead of amine a-2.
3.4g of compound 20 was obtained (yield 19%, mass [ m+ ] =924) by the same method as the production method of the compound 1 of production example 1, except that 18g of the intermediate 29 was used instead of the intermediate 2.
PREPARATION EXAMPLE 21 Synthesis of Compound 21
Except that 11g of a-21 was used instead of a-1, the production was performed in the same manner as the production method of intermediate 1 of production example 1, whereby 12g of intermediate 30 was obtained (yield 70%, mass [ m+ ] =413).
The production was performed in the same manner as in production example 1. Production of intermediate 2, except that 12g of intermediate 30 was used instead of intermediate 1 and 13.5g of a-22 was used instead of amine a-2, thereby obtaining 17g of intermediate 31 (yield 70%, mass [ m+ ] =839).
3.2g of compound 21 was obtained (yield 19%, mass [ m+ ] =813) by performing the same method as the production method of compound 1 of production example 1, except that 17g of intermediate 31 was used instead of intermediate 2.
PREPARATION EXAMPLE 22 Synthesis of Compound 22
The production was carried out in the same manner as in production example 1 except that 10g of 1-bromo-3-chloro-5-methylbenzene was used instead of 1-bromo-2, 3-dichloro-5-methylbenzene and 22g of amine a-23 was used instead of amine a-1, whereby 21g of intermediate 32 was obtained (yield 74%, mass [ m+ ] =581).
21g of intermediate 32, 4.4g of 2, 4-dimethylaniline, 5.2g of sodium tert-butoxide, 0.36g of bis (tri-tert-butylphosphine) palladium (0) (Pd (P (t-Bu)) were reacted under a nitrogen atmosphere 3 ) 2 ) After addition to 300mL of toluene, the mixture was heated and stirred at 120℃for 4 hours. After the completion of the amination reaction, 6.9g of 1-bromo-3-chlorobenzene was immediately added dropwise thereto, followed by stirring for 2 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl, after separation, mgSO was used 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 17g of intermediate 33 (yield 61%, mass [ M+)]＝776)。
17g of intermediate 33 are dissolved in dichlorobenzene under nitrogen atmosphere, 14g of boron triiodide (BI 3 ) After that, the mixture was heated to 130℃and stirred for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, dissolved in toluene, extracted, and dried over MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane), thereby5.5g of intermediate 34 (yield 32%, mass [ M+)]＝784)。
The production was performed in the same manner as in production example 1. Production of intermediate 2, except that 5.5g of intermediate 34 was used instead of intermediate 1 and 1.2g of a-5 was used instead of amine a-2, whereby 17g of compound 22 was obtained (yield 81%, mass [ m+ ] =917).
PREPARATION EXAMPLE 23 Synthesis of Compound 23
The production was performed in the same manner as the production method of intermediate 2 in production example 1, except that 15g of intermediate 8 was used instead of intermediate 1 and 13g of a-18 was used instead of amine a-2, whereby 20g of intermediate 35 was obtained (yield 75%, mass [ m+ ] =1061).
3.5g of compound 23 was obtained (yield 18%, mass [ m+ ] =1035) by the same method as that for producing compound 1 of production example 1, except that 20g of intermediate 35 was used instead of intermediate 2.
PREPARATION EXAMPLE 24 Synthesis of Compound 24
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After 50.0g of 1.3-dibromo-2-chloro-5-iodobenzene (1, 3-dibromo-2-chloro-5-iodobenzene) was dissolved in 1.2L of Tetrahydrofuran (THF) under a nitrogen atmosphere, the temperature was maintained to-10 ℃. Then, 70mL (2.0M tetrahydrofuran solution) of isopropyl magnesium chloride (isopropylmagnesium chloride) was slowly added dropwise thereto, followed by stirring at 0℃for 1 hour. 37.2g of triphenylchlorosilane were added at the same temperature. After the reaction solution was warmed to 0℃and stirred for about 1 hour, it was further stirred at room temperature for 12 hours. Then, after dilution with ethyl acetate, saturated NH was added 4 Cl solution (Saturated aq. NH) 4 Cl), the reaction was completed, and the organic layer was extracted with MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled under reduced pressureRemoved and purified by recrystallization (toluene/hexane) to obtain 36g of intermediate 36 (yield 54%, mass [ M+)]＝529)。
The production was performed in the same manner as in production example 2. Production of intermediate 3, except that 20g of intermediate 36 was used instead of 2-bromo-1, 3-diiodo-5-methylbenzene and 21g of amine a-1 was used instead of amine a-2, whereby 25g of intermediate 37 was obtained (yield 71%, mass [ m+ ] =930).
The production was performed in the same manner as in production example 1 using 25g of intermediate 37 instead of intermediate 2, whereby 4.6g of compound 24 was obtained (yield 19%, mass [ m+ ] =904).
PREPARATION EXAMPLE 25 Synthesis of Compound 25
The production was performed in the same manner as in production example 2. Production of intermediate 3, except that 15g of 1, 3-dibromo-2-chlorobenzene was used instead of 2-bromo-1, 3-diiodo-5-methylbenzene, whereby 28g of intermediate 38 was obtained (yield 75%, mass [ m+ ] =672).
Except that 28g of intermediate 38 was used instead of intermediate 2, the production was performed in the same manner as in production example 1, whereby 6.8g of intermediate 39 was obtained (yield 25%, mass [ m+ ] =645).
6.8g of intermediate 39 was dissolved in 100mL of chloroform under nitrogen atmosphere, and 1.9g of N-bromosuccinimide was added over 30 minutes, followed by stirring at room temperature for 4 hours. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted with MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by column chromatography (developing solution: hexane/ethyl acetate=1:1 (volume ratio)) to obtain 5.2g of intermediate 40 (yield 68%, mass [ m+)]＝724)。
After dissolving 5.2g of intermediate 40 in 60mL of tetrahydrofuran (anhydrous THF) under nitrogen, the temperature was increasedThe temperature was reduced to-78 ℃. Then, 5.7mL of n-butyllithium (n-BuLi (2.5M in hexane)) was slowly added dropwise thereto, followed by stirring for 1 hour. At the end of the lithium halide exchange reaction, 1.2mL of trimethylchlorosilane was dissolved in 5mL of tetrahydrofuran (anhydrous) and then slowly added dropwise. After the reaction solution was stirred at-78℃for about 1 hour, the organic layer was extracted with dichloromethane and was dried over MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by column chromatography (developing solution: hexane/ethyl acetate=1:1 (volume ratio)) to obtain 3.5g of compound 25 (yield 68%, mass [ m+) ]＝747)。
PREPARATION EXAMPLE 26 Synthesis of Compound 26
22g of intermediate 41 (yield 75%, mass [ m+ ] =860) was obtained by producing the same method as that for producing intermediate 2 of production example 1, except that 16g of a-24 was used instead of the amine a-2.
4.2g of compound 26 (yield 20%, mass [ m+ ] =833) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 14g of the intermediate 41 was used instead of the intermediate 2.
Preparation example 27 Synthesis of Compound 27
Except that 12.6g of a-25 was used instead of the amine a-2, the production was performed in the same manner as in the production method of intermediate 2 of production example 1, whereby 20g of intermediate 42 was obtained (yield 76%, mass [ m+ ] =773).
4.1g of compound 27 was obtained (yield 21%, mass [ m+ ] =746) by the same method as in production example 1, except that 20g of intermediate 42 was used instead of intermediate 2.
PREPARATION EXAMPLE 28 Synthesis of Compound 28
The production was performed in the same manner as the production method of intermediate 2 in production example 1, except that 15g of intermediate 21 was used instead of intermediate 1 and a-26 was used instead of amine a-2, whereby 17g of intermediate 43 was obtained (yield 67%, mass [ m+ ] =1106).
3.6g of compound 28 (yield 22%, mass [ m+ ] =1079) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 17g of the intermediate 43 was used instead of the intermediate 2.
Preparation example 29 Synthesis of Compound 29
Except that 12.8g of a-27 was used instead of a-1, the production was performed in the same manner as in the production method of intermediate 1 of production example 1, whereby 16g of intermediate 44 was obtained (yield 70%, mass [ m+ ] =365).
The production was performed in the same manner as the production method of intermediate 2 in production example 1, except that 16g of intermediate 44 was used instead of intermediate 1 and 22g of a-18 was used instead of amine a-2, whereby 26g of intermediate 45 was obtained (yield 71%, mass [ m+ ] =832).
Except that 17g of intermediate 45 was used instead of intermediate 2, the production was performed in the same manner as the production method of compound 1 of production example 1, whereby 4.1g of compound 29 was obtained (yield 16%, mass [ m+ ] =805).
Preparation example 30 Synthesis of Compound 30
22g of intermediate 46 was obtained (yield 70%, mass [ m+ ] =926) by the same method as that for producing intermediate 2 of production example 1, except that 17.8g of a-28 was used instead of the amine a-2.
4.3g of compound 30 was obtained (yield 20%, mass [ m+ ] =900) by the same method as the production method of the compound 1 of production example 1, except that 22g of the intermediate 46 was used instead of the intermediate 2.
PREPARATION EXAMPLE 31 Synthesis of Compound 31
20g of intermediate 7, 4.6g of 2-fluoroboric acid, 11.7g of potassium phosphate [ potassium phosphate ] are added]220mL of 1, 4-bisAfter alkane and 50mL of water, 0.48g of tetrakis (triphenylphosphine) palladium (0) [ tetrakis (triphenylhosphine) paladium (0) was added](Pd(PPh 3 ) 4 ) After that, the mixture was heated and stirred for 16 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 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 9.5g of intermediate 47 (yield 66%, mass [ M+)]＝521)。
14g of intermediate 48 (yield 78%, mass [ m+ ] =982) was obtained by producing the same method as that for producing intermediate 2 of production example 1, except that 9.1g of a-29 was used instead of the amine a-2.
3.2g of compound 31 (yield 23%, mass [ m+ ] =956) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 14g of the intermediate 48 was used instead of the intermediate 2.
PREPARATION EXAMPLE 32 Synthesis of Compound 32
Except that 4.6g of a-30 was used instead of the amine a-5, the production was performed in the same manner as in the production method of intermediate 8 of production example 5, whereby 12g of intermediate 49 was obtained (yield 73%, mass [ m+ ] =592).
The production was performed in the same manner as in production example 1. Production of intermediate 2, except that 12g of intermediate 49 was used instead of intermediate 1 and 7.0g of a-31 was used instead of amine a-2, whereby 13g of intermediate 50 was obtained (yield 71%, mass [ m+ ] =899).
2.9g of compound 32 (yield 23%, mass [ m+ ] =873) was obtained by producing the compound by the same method as the production method of the compound 1 of production example 1, except that 13g of the intermediate 50 was used instead of the intermediate 2.
PREPARATION EXAMPLE 33 Synthesis of Compound 33
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14g of intermediate 51 was obtained (yield 69%, mass [ m+ ] =739) by the same method as that for producing intermediate 8 of production example 5, except that 8.7g of a-31 was used instead of the amine a-5.
Except that 14g of intermediate 51 was used instead of intermediate 1, the same procedure as in production example 1 was followed to obtain 16g of intermediate 52 (yield 76%, mass [ m+ ] =1108).
3.4g of compound 33 was obtained (yield 22%, mass [ m+ ] =1081) by the same method as the production method of compound 1 of production example 1, except that 16g of intermediate 52 was used instead of intermediate 2.
Production example 34: production of Compound E1
10g of spiro [ fluorene ]-9,9' -thioxanthene]-1-ylboronic acid and 8.8g of the above-mentioned compound 2- ([ 1,1' -biphenyl)]After complete dissolution of the-4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 84%) of compound E1 was produced. MS [ M+H ]] + ＝657。
Production example 35: production of Compound E2
10g of spiro [ fluorene-9, 9' -xanthene]After complete dissolution of 2-ylboronic acid and 9.8g of the above compound 2-chloro-4, 6-di (naphthalen-1-yl) -1,3, 5-triazine in tetrahydrofuran (200 mL), 11.1g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 15g (yield 85%) of compound E2 was produced. MS [ M+H ] ] + ＝665。
Production example 36: production of Compound E3
/>
10g of spiro [ fluorene-9, 9' -xanthene]After complete dissolution of 2-ylboronic acid and 8.5g of the above compound 4- (4-chlorophenyl) -2-phenylquinazoline in tetrahydrofuran (200 mL), 11.1g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 86%) of compound E3 was produced. MS [ M+H ]] + ＝614
Production example 37: production of Compound E4
10g of spiro [ fluorene-9, 9' -thioxanthene]After complete dissolution of 3-ylboronic acid and 8.5g of the above compound 4- (4-chlorophenyl) -2, 6-diphenylpyrimidine in tetrahydrofuran (200 mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 13g (yield 78%) of compound E4 was produced. MS [ M+H ]] + ＝656
Production example 38: production of Compound E5
10g of spiro [ fluorene-9, 9' -thioxanthene]After complete dissolution of 4-ylboronic acid and 6.8g of the above compound 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 10.6g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 11g (yield 77%) of compound E5 was produced. MS [ M+H ]] + ＝565
Production example 39: production of Compound E6
10g of spiro [ dibenzo [ c, h ]]Xanthene-7, 9' -fluorene]After complete dissolution of the 2' -ylboronic acid and 5.6g of the above compound 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 8.7g of carbonic acid was addedPotassium was dissolved in 60mL of water and added. After 0.8g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 11g (yield 79%) of compound E6 was produced. MS [ M+H ]] + ＝665
Production example 40: production of Compound E7
10g of spiro [ fluorene-9, 9' -xanthene ]After complete dissolution of 2-ylboronic acid and 11.5g of the above compound 9- (4- (6-chloro-2-phenylpyrimidin-4-yl) phenyl) -9H-carbazole in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 72%) of compound E7 was produced. MS [ M+H ]] + ＝729。
Production example 41: production of Compound E8
10g of spiro [ fluorene-9, 9' -xanthene]-2-Ylboronic acid and 11.2g of the above-mentioned compound 2-chloro-4-phenyl-6- (4 '- (pyridin-4-yl) - [1,1' -biphenyl)]After complete dissolution of the-3-yl) -1,3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 73%) of compound E8 was produced. MS [ M+H ]] + ＝718
Production example 42: production of Compound E9
10g of (3 '- (2, 6-diphenylpyrimidin-4-yl) spiro [ fluorene-9, 9' -xanthene)]After complete dissolution of 2-yl) boric acid and 4.4g of the above compound 4-chloro-2, 6-diphenylpyrimidine in tetrahydrofuran (200 mL), 6.9g of potassium carbonate was dissolved in 60mL of water and added. After 0.6g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 10g (yield 76%) of compound E9 was produced. MS [ M+H ]] + ＝794。
Production example 43: production of Compound E10
10g of spiro [ fluorene-9, 9' -xanthene]After complete dissolution of 2' -ylboronic acid and 11.5g of the above compound 2-chloro-4- (4-dibenzofuran-4-yl-phenyl) -6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 16g (yield 82%) of compound E10 was produced. MS [ M+H ] ] + ＝731。
Production example 44: production of Compound E11
10g of spiro [ fluorene-9, 9' -xanthene]After complete dissolution of 3' -ylboronic acid and 11.7g of the above compound 2- (2-bromonaphthalen-1-yl) -4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. Adding 0.9g of SizhuTriphenylphosphine) palladium, and stirring for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 15g (yield 82%) of compound E11 was produced. MS [ M+H ]] + ＝691。
Production example 45: production of Compound E12
10g of spiro [ fluorene-9, 9' -xanthene]After complete dissolution of 3' -ylboronic acid and 9.2g of the above compound 2- (6-chloropyridin-3-yl) -4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 13g (yield 76%) of compound E12 was produced. MS [ M+H ] ] + ＝642。
Production example 46: production of Compound E13
10g of spiro [ fluorene-9, 9' -thioxanthene]After completely dissolving 3' -ylboronic acid and 10.1g of the above 2- (5-bromothiophen-2-yl) -4, 6-diphenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 13g (yield 77%) of compound E13 was produced. MS [ M+H ]] + ＝663。
Production example 47: production of Compound E14
10g of spiro [ fluorene-9, 9' -thioxanthene]After complete dissolution of 4' -ylboronic acid and 11.9g of the above 10- (4- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) phenyl) -10H-phenothiazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 16g (yield 81%) of compound E14 was produced. MS [ M+H ] ] + ＝778。
Production example 48: production of Compound E15
10g of spiro [ fluorene-9, 9' -thioxanthene]-4' -ylboronic acid and 9.4g of the above-mentioned 4' - (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) - [1,1' -biphenyl ]]After complete dissolution of 2-nitrile in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 81%) of compound E15 was produced. MS [ M+H ]] + ＝682。
Production example 49: production of Compound E16
10g of (13, 13-dimethyl-13H-indeno [1, 2-l)]Phenanthrene 11-yl) boronic acid and 10.2g of the abovementioned 2- ([ 1,1' -biphenyl)]After complete dissolution of the-2-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After adding 1.0g of tetrakis (triphenylphosphine) palladium, the mixture was stirred with heating for 8 hours. Cooling to room temperature, and formingAfter the beam reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 79%) of compound E16 was produced. MS [ M+H ] ] + ＝603。
Production example 50: production of Compound E17
10g of (9, 9-diphenyl-9H-fluoren-4-yl) boronic acid and 11.5g of the abovementioned 2- ([ 1,1':3', 1' -terphenyl) boronic acid are reacted]After complete dissolution of the-5' -yl) -4-chloro-6-phenyl-1, 3, 5-triazine in tetrahydrofuran (200 mL), 11g of potassium carbonate was dissolved in 60mL of water and added. After adding 1.0g of tetrakis (triphenylphosphine) palladium, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 15g (yield 77%) of compound E17 was produced. MS [ M+H ]] + ＝703。
Production example 51: production of Compound E18
10g of (9, 9-dimethyl-7-phenyl-9H-fluoren-4-yl) boronic acid and 12.5g of 2- ([ 1,1' -biphenyl)]After complete dissolution of the-4-yl) -4-chloro-6- (naphthalen-1-yl) -1,3, 5-triazine in tetrahydrofuran (200 mL), 13.2g of potassium carbonate was dissolved in 60mL of water and added. After adding 1.1g of tetrakis (triphenylphosphine) palladium, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 16g (yield 80%) of compound E18 was produced. MS [ M+H ] ] + ＝629。
Production example 52: production of Compound E19
10g of (9, 9-diphenyl-9H-fluoren-2-yl) boronic acid and 12.3g of 2- ([ 1,1' -biphenyl)]After complete dissolution of the-3-yl) -4-chloro-6- (phenanthren-9-yl) -1,3, 5-triazine in tetrahydrofuran (200 mL), 13.2g of potassium carbonate was dissolved in 60mL of water and added. After adding 1.0g of tetrakis (triphenylphosphine) palladium, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 15g (yield 75%) of compound E19 was produced. MS [ M+H ]] + ＝727。
Production example 53: production of Compound E20
10g of (9, 9-diphenyl-9H-fluoren-1-yl) boronic acid and 10.6g of 2- ([ 1,1' -biphenyl)]After complete dissolution of the-2-yl) -4-chloro-6- (naphthalen-2-yl) -1,3, 5-triazine in tetrahydrofuran (200 mL), 11.1g of potassium carbonate was dissolved in 60mL of water and added. After 0.9g of tetrakis (triphenylphosphine) palladium was added, the mixture was stirred with heating for 8 hours. The temperature was lowered to ambient temperature, and after completion of the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with tetrahydrofuran and ethyl acetate, whereby 14g (yield 79%) of compound E20 was produced. MS [ M+H ] ] + ＝677。
The heterocyclic compounds of the chemical formulas 1 and 2 described in the present specification can be produced by appropriately combining the production formulas described in the examples of the present specification and the intermediates described above based on common technical knowledge.
< 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. At this time, washThe detergent was a product of fei-hill co., and the distilled water was distilled water filtered twice using a Filter (Filter) manufactured by millbore co., ltd. 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 usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HAT compound +. >And HT-A compounds of the following->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.
Then, on the electron blocking layer, the film thickness is set to beThe BH-1 Compound and Compound 1 (Compound 1) were vacuum-evaporated at a weight ratio of 100:2 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 ET and the following LThe iQ compound was vacuum evaporated in a weight ratio of 1:1, thus giving +.>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 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 18 and comparative examples 1 to 8
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the dopant material and the hole blocking layer material of the light-emitting layer were each as described in table 1 below.
For the above examples 1 to 18 and comparisonThe organic light-emitting devices of examples 1 to 8 were 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 95% with respect to the initial luminance was measured and labeled. The results are shown in Table 1 below.
TABLE 1
In the above table, as the dopant of the light emitting layer and the hole blocking layer substance, all of the comparative examples 1 to 3 used compounds different from the compounds of chemical formulas 1 and 2 of the present invention. Examples 1 to 18 exhibited low voltage and high efficiency characteristics compared with comparative examples 1 to 3, and in particular, it was confirmed that the lifetime was greatly increased.
Comparative examples 4 to 8 used the compound of the present invention as either one of the dopant of the light-emitting layer and the hole blocking layer substance. When example 1 and comparative example 4, example 4 and comparative example 5, and example 12 and comparative example 6 were compared, respectively, it was found that the same substance was used as a dopant substance for the light-emitting layer, but the substance for the hole blocking layer was different, and thus, an effect difference was exhibited when applied to a device. Examples 1, 4 and 12 were confirmed to have low voltage, high efficiency and long life characteristics compared with comparative examples 4, 5 and 6.
Examples 2 and 7, examples 9, 18 and 8 are each device materials using the same hole blocking material and different dopant materials. Examples 2, 9 and 18 were confirmed to have low voltage, high efficiency and long life characteristics compared with comparative examples 7 and 8 due to the difference in dopant species.
< device example 2>
Example 19
ITO (indium tin oxide) toThe glass substrate coated into a film is put into distilled water in which a detergent is dissolvedWashing was performed by 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 usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HAT compound +. >And HT-A compounds of the following->Vacuum evaporation is performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe BH-2 compound and the following compound 2 were vacuum-evaporated at a weight ratio of 100:2 to form a light-emitting layer.
On the light-emitting layer, a compound E10 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.
In the process, the evaporation rate 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 20 to 28 and comparative examples 9 to 16
An organic light-emitting device was manufactured in the same manner as in example 19 above, except that the dopant material of the light-emitting layer and the electron injection and transport layer material described in table 2 below were used.
The organic light-emitting devices of examples 19 to 28 and comparative examples 9 to 16 described above were subjected to a temperature of 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 95% with respect to the initial luminance was measured and labeled. The results are shown in Table 2 below.
TABLE 2
In table 2 above, as the dopant of the light-emitting layer and the hole blocking layer substance, all of comparative examples 9 to 11 used compounds different from the compounds of chemical formulas 1 and 2 of the present invention.
Examples 19 to 28 can be confirmed to exhibit low voltage, high efficiency and long life characteristics as compared with comparative examples 9 to 11.
The same dopant species as in examples 19, 20 and 24 were used in comparative examples 12 to 14, respectively, and different species were used only in the electron injection and transport layers. Examples 19, 20 and 24 showed characteristics of low voltage, high efficiency, and long life compared with comparative examples 12 to 14.
Comparative examples 15 and 16 used the same electron injection and transport layer materials as examples 24, 26 and 23, 28, respectively. However, the dopant species were different, and it was confirmed that examples 24, 26 and 23, 28 each showed more excellent effects when applied to devices, as compared with comparative examples 15 and 16.
< device example 3>
Example 29
ITO (indium tin oxide) to The 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 usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HAT compound +.>And HT-A compounds of the following->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.
Then, on the electron blocking layer, the film thickness is set to beThe BH-3 compound and the compound 5 were vacuum-evaporated at a weight ratio of 100:2 to form a light-emitting layer.
Vacuum evaporating the compound E10 on the light-emitting layer to obtainForm a hole blocking layer. On the hole blocking layer, a compound E2 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 above process, the organic matterThe vapor deposition rate is maintained at 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 30 to 34 and comparative examples 17 to 19
An organic light-emitting device was manufactured in the same manner as in example 29 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.
The organic light-emitting devices of examples 29 to 34 and comparative examples 17 to 19 described above were subjected to a temperature of 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 95% with respect to the initial luminance was measured and labeled. The results are shown in Table 3 below.
TABLE 3
In table 3 above, comparative example 17 is data in which all of the compounds not of the chemical formula of the present invention were used as dopant substances, hole blocking layer substances, electron injection and transport layer substances. Comparative example 18 used the same hole blocking layer material as in example 29, except for the dopant material, and the electron injection and transport layer material.
Comparative example 19 uses the same electron injection and transport layer materials as in example 34, with different materials being used in the dopant and hole blocking layer. Therefore, the excellent effects of low voltage, high efficiency, and long life in examples 29 and 34 can be confirmed as compared with comparative examples 18 and 19.
Claims (12)
1. An organic light emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises: a first organic layer including a compound represented by the following chemical formula 1 and a second organic layer including a compound represented by the following chemical formula 2:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
A1, A2, A3, B1 and B2 are the same or different from each other and each independently a hydrocarbon ring,
r1 to R5 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 alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, or substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3-1, at least one of R1 to R5 is represented by the following chemical formula 3-1,
chemical formula 3-1
In the chemical formula 3-1 described above,
the dotted line is the part connected with A1, A2, A3, B1 or B2,
r11 is a substituted or unsubstituted alkyl group,
r12 is a substituted or unsubstituted aryl group,
r13 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
n1 and n5 are each an integer of 0 to 4,
n2 and n4 are each integers from 0 to 5,
n3 is an integer of 0 to 3,
n1+n2+n3+n4+n5 is 1 or more,
when n1 to n5 are 2 or more, the substituents in brackets are the same or different from each other,
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
Y31 and Y32 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other to form a substituted or unsubstituted ring,
r3-1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or formula 4 below, or is combined with an adjacent group to form a hydrocarbon ring,
a31 is an integer of 0 to 8,
when a31 is plural, R3-1 are the same or different from each other,
chemical formula 4
In the chemical formula 4 described above, the chemical formula,
the dashed line is the site of attachment to the nucleus,
Ar 41 and Ar is a group 42 Are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
X 1 to X 3 Identical to or different from each other, are each independently N or CR,
X 1 to X 3 At least one of which is N,
r is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted heterocyclic group,
L 1 To L 3 Are identical or different from one another and are each independently directly bonded, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.
2. The organic light emitting device of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1:
chemical formula 1-1
In the chemical formula 1-1, R1 to R5 and n1 to n5 are as defined in the chemical formula 1.
3. The organic light-emitting device according to claim 1, wherein R1, R2, R4, and R5 are the same or different from each other, each being independently hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 carbon atoms which is 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, a cyano group and an alkyl group of 1 to 10 carbon atoms or with 2 or more groups selected from the group; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the chemical formula 3-1,
r3 is hydrogen; deuterium; a halogen group; cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; cycloalkyl having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an arylamine group having 6 to 60 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, an aryl group having 6 to 30 carbon atoms, and a silyl group, or with 2 or more groups selected from the group; aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, halogen groups, or cyano groups; a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or represented by the chemical formula 3-1.
4. The organic light emitting device of claim 1, wherein the chemical formula 2 is represented by the following chemical formula 2-1:
chemical formula 2-1
In the chemical formula 2-1 described above,
y is CR111R112, O or S,
r111, R112, R3-2 and R3-3 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, a substituted or unsubstituted heteroaryl group, or the following chemical formula 5, or are bonded to each other with adjacent groups to form a hydrocarbon ring,
l31 and L32 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
a33 is an integer of 0 to 8,
b33 is an integer of 0 to 8,
a33 and b33 are plural, the substituents in parentheses are the same or different from each other,
n33 is 0 or 1 and is preferably selected from the group consisting of,
when n33 is 0, hydrogen is bonded to each of the 2 benzene rings bonded to Y,
chemical formula 5
The dashed line is the site of attachment to the nucleus,
Ar 1 and Ar is a group 2 Are the same or different from each other, each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
X 1 to X 3 Identical to or different from each other, are each independently N or CR,
X 1 To X 3 At least one of which is N,
r are identical or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile 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 cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group,
L 1 to L 3 Are identical or different from one another and are each independently directly bonded, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.
5. The organic light-emitting device according to claim 4, wherein Y is O or S.
6. The organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
7. the organic light-emitting device according to claim 1, wherein the chemical formula 2 is any one of the following compounds:
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8. the organic light-emitting device according to claim 1, wherein the chemical formula 2 is any one of compounds described in the following table:
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9. 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 disposed between the second electrode and the first organic layer.
10. 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.
11. 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.
12. 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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| KR20190093179 | 2019-07-31 | ||
| KR10-2019-0093179 | 2019-07-31 | ||
| PCT/KR2020/010175 WO2021020947A1 (en) | 2019-07-31 | 2020-07-31 | Organic light-emitting device |
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| US20230303594A1 (en) * | 2020-06-18 | 2023-09-28 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| CN113594395B (en) * | 2021-08-26 | 2024-04-12 | 长春海谱润斯科技股份有限公司 | Organic electroluminescent device |
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| WO2021020947A1 (en) | 2021-02-04 |
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