CN112789747A - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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CN112789747A
CN112789747A CN202080005495.0A CN202080005495A CN112789747A CN 112789747 A CN112789747 A CN 112789747A CN 202080005495 A CN202080005495 A CN 202080005495A CN 112789747 A CN112789747 A CN 112789747A
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substituted
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deuterium
organic light
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韩修进
李东勋
张焚在
徐尚德
郑珉祐
李征夏
朴瑟灿
黄晟现
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LG Chem Ltd
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Priority claimed from PCT/KR2020/010441 external-priority patent/WO2021029616A1/en
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract

The present invention provides an organic light emitting device having improved driving voltage and/or lifetime by including two types of host compounds in a light emitting layer.

Description

Organic light emitting device
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0097650 at 8/9/2019 and korean patent application No. 10-2020-0097980 at 8/5/2020, the entire contents of the documents containing the korean patent application are incorporated herein by reference.
The present invention relates to an organic light emitting device.
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 has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document (patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to an organic light emitting device.
Means for solving the problems
The present invention provides an organic light emitting device comprising:
an anode;
a cathode provided to face the anode; and
a light-emitting layer between the anode and the cathode,
the light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:
[ chemical formula 1]
Figure BDA0003002851710000021
In the above-described chemical formula 1,
x is O or S, and X is O or S,
X1to X3Each independently is N or CH, however, X1To X3At least one of which is N,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S2-60(ii) a heteroaryl group, wherein,
R1to R3Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60Alkenyl radical(ii) a Substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S2-60(ii) a heteroaryl group, wherein,
a + b is an integer of 0 to 6,
c is an integer of 0 to 8,
[ chemical formula 2]
Figure BDA0003002851710000031
In the above-described chemical formula 2,
a is a benzene ring condensed with two adjacent five-membered rings,
Ar3and Ar4Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S2-60(ii) a heteroaryl group, wherein,
R4is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S2-60(ii) a heteroaryl group, wherein,
d is an integer of 0 to 10,
a. when b, c and d are each 2 or more, the substituents in parentheses may be the same or different from each other.
Effects of the invention
The above-described organic light emitting device includes 2 host compounds in the light emitting layer, so that efficiency, driving voltage, and/or life span characteristics can be improved in the organic light emitting device.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 8, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
In the context of the present specification,
Figure BDA0003002851710000032
or
Figure BDA0003002851710000033
Represents a bond to other substituents, D represents deuterium, and Ph represents a phenyl group.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio radicals (A), (B), (C), (D), (
Figure BDA0003002851710000043
alkyl thio xy); arylthio radicals (A), (B), (C
Figure BDA0003002851710000044
Figure BDA0003002851710000045
aryl thio xy); alkylsulfonyl (
Figure BDA0003002851710000046
alkyl sulfoxy); arylsulfonyl (
Figure BDA0003002851710000047
aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituents formed by connecting 2 or more substituents of the above-exemplified substituents. For example, "2 or more substituents are attachedThe "substituent joined to" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
Figure BDA0003002851710000041
In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
Figure BDA0003002851710000042
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
Figure BDA0003002851710000051
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a triphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
Figure BDA0003002851710000061
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
Figure BDA0003002851710000062
And the like. But is not limited thereto.
In the present specification, the heteroaryl group is a heterocyclic group containing 1 or more heteroatoms of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Figure BDA0003002851710000063
Azolyl group,
Figure BDA0003002851710000064
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinylPyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo
Figure BDA0003002851710000065
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Figure BDA0003002851710000066
Examples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group can be applied to the above description about the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.
Provided is a light emitting device including: the light-emitting device includes an anode, a cathode provided to face the anode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2.
The organic light emitting device according to the present invention simultaneously includes 2 compounds having a specific structure as host substances in a light emitting layer, so that efficiency, driving voltage, and/or lifetime characteristics can be improved in the organic light emitting device.
The present invention will be described in detail below with reference to the respective configurations.
An anode and a cathode
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material 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); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
Hole injection layer
The organic light emitting device according to the present invention may include a hole injection layer between the anode and a hole transport layer, which will be described later, as necessary.
The hole injection layer is located on the anode, is a layer for injecting holes from the anode, and contains a hole injection substance. As such a hole injecting substance, the following compounds are preferred: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. In particular, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer.
Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
Hole transport layer
The organic light emitting device according to the present invention may include a hole transport layer between the anode and the light emitting layer. The hole transport layer is a layer that receives holes from the anode or a hole injection layer formed on the anode and transports the holes to the light-emitting layer, and contains a hole transport substance. The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
Electron blocking layer
The organic light emitting device according to the present invention may include an electron blocking layer between the hole transport layer and the light emitting layer as necessary. The electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, preventing excessive electron transfer, and increasing the hole-electron binding ratio. The electron blocking layer includes an electron blocking material, and an arylamine organic material or the like can be used as an example of such an electron blocking material, but the electron blocking material is not limited thereto.
Luminescent layer
The organic light-emitting device according to the present invention includes a light-emitting layer between an anode and a cathode, and the light-emitting layer contains the first compound and the second compound as host substances. Specifically, the first compound functions as an N-type host material having an electron transport ability superior to a hole transport ability, and the second compound functions as a P-type host material having a hole transport ability superior to an electron transport ability, whereby the ratio of holes to electrons in the light-emitting layer can be appropriately maintained. Accordingly, excitons (exiton) uniformly emit light throughout the entire light emitting layer, so that the light emitting efficiency and the lifetime characteristic of the organic light emitting device can be simultaneously improved.
Next, the first compound and the second compound will be described in order.
(first Compound)
The first compound is represented by the above chemical formula 1. Specifically, the first compound is a compound in which a carbazolyl group and an N-containing six-membered heterocyclic group are simultaneously substituted in a dibenzofuran/dibenzothiophene core, and such a compound has a better intramolecular charge transfer than a compound having no such substituent, and thus has a higher molecular stability and can efficiently transfer holes and electrons. Further, such an effect can be further maximized in the case where the second compound is used as a host of the light-emitting layer as described later.
Further, the first compound may include at least one deuterium.
More specifically, in the above chemical formula 1, Ar1And Ar2At least one of which is C substituted by deuterium6-60An aryl group; or C substituted by deuterium containing more than 1 heteroatom of N, O and S2-60Heteroaryl, or
R1To R3At least one of which is deuterium; c substituted by deuterium6-60An aryl group; or C substituted by deuterium containing more than 1 heteroatom of N, O and S2-60The heteroaryl group, a + b + c, may be 1 or more, or an integer of 1 to 14.
Or, Ar1And Ar2At least one of which is C substituted by deuterium6-60An aryl group; or C substituted by deuterium containing more than 1 heteroatom of N, O and S2-60Heteroaryl, and R1To R3At least one of which is deuterium; c substituted by deuterium6-60An aryl group; or C substituted by deuterium containing more than 1 heteroatom of N, O and S2-60The heteroaryl group, a + b + c, may be 1 or more.
In this case, the first compound may be represented by the following chemical formula 1':
[ chemical formula 1' ]
Figure BDA0003002851710000091
In the above chemical formula 1',
R21to R24One of them is
Figure BDA0003002851710000092
The remainder being each independently referred to R2Definition of (A), R11To R14One of them is
Figure BDA0003002851710000093
The remainder being each independently referred to R1Is defined as either
R21To R24Each independently of the other with reference to R2Definition of (A), R14Is composed of
Figure BDA0003002851710000101
R11To R13One of them is
Figure BDA0003002851710000102
The remainder being each independently referred to R1The definition of (1).
In addition, in the case where the first compound is represented by the above chemical formula 1', intramolecular charge transfer and molecular stability may be more advantageous than those of a compound in which a carbazolyl group and an N-containing six-membered-heterocyclic group are substituted at different positions.
More specifically, the above-described first compound may be represented by any one of the following chemical formulas 1A 'to 1E':
[ chemical formula 1A' ]
Figure BDA0003002851710000103
[ chemical formula 1B' ]
Figure BDA0003002851710000104
[ chemical formula 1C' ]
Figure BDA0003002851710000111
[ chemical formula 1D' ]
Figure BDA0003002851710000112
[ chemical formula 1E' ]
Figure BDA0003002851710000113
In the above chemical formulas 1A 'to 1E',
X、X1to X3、Ar1、Ar2、R1To R3A + b and c are the same as defined in the above chemical formula 1.
At this time, in the above chemical formulas 1A 'to 1D', a and b are each an integer of 0 to 3,
in the above chemical formula 1E', a is an integer of 0 to 2, and b is an integer of 0 to 4.
More specifically, the compound represented by the above chemical formula 1C' may be represented by the following chemical formula 1A (No. 6 position of core), chemical formula 1B (No. 7 position of core), chemical formula 1C (No. 8 position of core), or chemical formula 1D (No. 9 position of core), depending on the substitution position of the N-containing six-membered heterocyclic group:
[ chemical formula 1A ]
Figure BDA0003002851710000121
[ chemical formula 1B ]
Figure BDA0003002851710000122
[ chemical formula 1C ]
Figure BDA0003002851710000123
[ chemical formula 1D ]
Figure BDA0003002851710000124
In the above chemical formulas 1A to 1D,
a and b are each an integer of 0 to 3,
the description for the remaining substituents is the same as that in the above chemical formula 1.
Preferably, X is O.
Preferably, X1To X3Are all N, or
X1And X2Is N, X3Is CH, or
X1And X3Is N, X2Is CH, or
X1Is N, X2And X3Is CH, or
Can be X2Is N, X1And X3Is CH.
Preferably, Ar1And Ar2Each independently is C6-20An aryl group; or C containing 1 or 2 heteroatoms of N, O and S2-20(ii) a heteroaryl group, wherein,
here, Ar is as defined above1And Ar2Unsubstituted or may be selected from deuterium, C1-10Alkyl and C6-20And 1 or more substituents in the aryl group.
More preferably, Ar1And Ar2Each independently is phenyl, biphenyl, naphthyl, phenanthryl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzo
Figure BDA0003002851710000132
An azole group or a benzothiazolyl group,
here, Ar is as defined above1And Ar2Unsubstituted or may be selected from deuterium, C1-10Alkyl and C6-20And 1 or more substituents in the aryl group.
For example, Ar1And Ar2May be any one selected from the following groups, but is not limited thereto:
Figure BDA0003002851710000131
Figure BDA0003002851710000141
in the above-mentioned group, the group,
m is an integer of 0 to 7.
In addition, Ar1And Ar2At least one of may be
Figure BDA0003002851710000142
In addition, Ar1And Ar2May be identical to each other. Or Ar1And Ar2May be different.
Preferably, R1To R3May each independently be deuterium; c unsubstituted or substituted by deuterium6-20An aryl group; or C comprising 1 heteroatom of N, O and S, unsubstituted or substituted by deuterium2-20A heteroaryl group.
Preferably, R1And R2May each independently be hydrogen, deuterium, phenyl substituted with 1 to 5 deuterium, carbazolyl, dibenzofuranyl or dibenzothiophenyl.
In addition, R3May be hydrogen, deuterium, phenyl unsubstituted or substituted with deuterium, carbazolyl unsubstituted or substituted with deuterium, dibenzofuranyl unsubstituted or substituted with deuterium, or dibenzothiophenyl unsubstituted or substituted with deuterium.
In addition, the substituent of the above chemical formula 1
Figure BDA0003002851710000151
May be any of substituents represented by the following chemical formulae 3a to 3 i:
Figure BDA0003002851710000152
in the above chemical formulas 3a to 3i,
p is an integer of 0 to 7,
q is an integer of 0 to 8.
In chemical formula 1, R represents1And R2A + b of the sum of the numbers of (a) and (b) may be 0,1, 2,3,4,5 or 6, and represents R3The number of c may be 0,1, 2,3,4,5,6,7 or 8.
Preferably, a + b is 0,1, 2 or 6, and c may be 0,1, 2 or 8. In this case, when a + b is 6, R1And R2May be all deuterium, and when c is 8, R3May be deuterium.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
Figure BDA0003002851710000161
Figure BDA0003002851710000171
Figure BDA0003002851710000181
Figure BDA0003002851710000191
Figure BDA0003002851710000201
Figure BDA0003002851710000211
Figure BDA0003002851710000221
Figure BDA0003002851710000231
Figure BDA0003002851710000241
Figure BDA0003002851710000251
Figure BDA0003002851710000261
Figure BDA0003002851710000271
Figure BDA0003002851710000281
Figure BDA0003002851710000291
Figure BDA0003002851710000301
Figure BDA0003002851710000311
Figure BDA0003002851710000321
Figure BDA0003002851710000331
Figure BDA0003002851710000341
Figure BDA0003002851710000351
Figure BDA0003002851710000361
Figure BDA0003002851710000371
Figure BDA0003002851710000381
Figure BDA0003002851710000391
Figure BDA0003002851710000401
Figure BDA0003002851710000411
Figure BDA0003002851710000421
Figure BDA0003002851710000431
Figure BDA0003002851710000441
Figure BDA0003002851710000451
Figure BDA0003002851710000461
Figure BDA0003002851710000471
Figure BDA0003002851710000481
Figure BDA0003002851710000491
Figure BDA0003002851710000501
Figure BDA0003002851710000511
Figure BDA0003002851710000521
Figure BDA0003002851710000531
Figure BDA0003002851710000541
Figure BDA0003002851710000551
Figure BDA0003002851710000561
Figure BDA0003002851710000571
Figure BDA0003002851710000581
Figure BDA0003002851710000591
Figure BDA0003002851710000601
Figure BDA0003002851710000611
Figure BDA0003002851710000621
Figure BDA0003002851710000631
Figure BDA0003002851710000641
Figure BDA0003002851710000651
Figure BDA0003002851710000661
on the other hand, as an example, the compound represented by the above chemical formula 1 may be produced by a production method as shown in the following reaction formula 1. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 1]
Figure BDA0003002851710000671
In the above reaction formula 3, XaAnd X' are each independently halogen, preferably, XaIs fluorine, X' is bromine or chlorine, and the definitions for the other substituents are the same as those described above.
Specifically, the compound represented by the above chemical formula 1 can be produced through the steps 1-1 and 1-2.
The above step 1-1 is a step of producing an intermediate compound A3 by Suzuki-coupling (Suzuki-coupling) reaction of starting materials a1 and a 2. Such Suzuki-coupling (Suzuki-coupling) reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the Suzuki-coupling (Suzuki-coupling) reaction can be appropriately modified.
In addition, the step 1-2 is a step of producing a compound represented by the above chemical formula 1 in which a carbazolyl group is introduced into the intermediate compound A3 by an amine substitution reaction with the intermediate compound A3 and the compound a4, and such an amine substitution reaction is preferably performed in the presence of a palladium catalyst and a base. Further, the reactive group used in the above-mentioned amine substitution reaction may also be appropriately modified according to the technique known in the art.
The method for producing the compound represented by the above chemical formula 1 can be further embodied in the production examples described later.
(second Compound)
The second compound is represented by chemical formula 2. Specifically, the second compound is obtained by substituting Ar on 2N atoms of an indolocarbazole nucleus3And Ar4A compound of a substituent. In particular, in the second compound, since the indolocarbazole structure has excellent hole characteristics, Ar is substituted with the indolocarbazole structure as a center3And Ar4And a substituent, whereby the electron transport property can be adjusted. Therefore, when the second compound is used in the light-emitting layer together with the first compound, the hole and electron transport properties can be adjusted in various ways, which is advantageous in coordinating charge balance in the light-emitting layer.
The above-mentioned second compound may be represented by any one of the following chemical formulas 2-1 to 2-5 according to the position at which the benzene ring as the a ring is fused with the adjacent two five-membered rings:
[ chemical formula 2-1]
Figure BDA0003002851710000681
[ chemical formula 2-2]
Figure BDA0003002851710000682
[ chemical formulas 2-3]
Figure BDA0003002851710000683
[ chemical formulas 2-4]
Figure BDA0003002851710000691
[ chemical formulas 2 to 5]
Figure BDA0003002851710000692
In the above chemical formulas 2-1 to 2-5,
R4each independently is deuterium; substituted or unsubstituted C6-20An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S2-20(ii) a heteroaryl group, wherein,
e is an integer of 0 to 4,
f is an integer of 0 to 2,
g is an integer of 0 to 4,
Ar3and Ar4The same as defined in the above chemical formula 2.
Preferably, Ar3And Ar4May be a hole-transporting substituent. Specifically, Ar3And Ar4Each independently is C6-60Aryl, carbazolyl, dibenzofuranyl or dibenzothienyl,
here, Ar is as defined above3And Ar4May be unsubstituted or selected from deuterium, C6-20Aryl, carbazolyl, phenylcarbazolyl, dibenzofuranyl and dibenzothiophenyl.
More preferably, Ar3And Ar4Each independently of the others is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, dibenzofuranyl or dibenzothiophenyl,
here, Ar is as defined above3And Ar4May be unsubstituted or substituted with 1 or more substituents selected from deuterium, phenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl and dibenzothiophenyl.
For example, Ar3And Ar4Can eachIndependently is any one selected from the following groups, but is not limited thereto:
Figure BDA0003002851710000701
further, preferably, R4May be deuterium; c unsubstituted or substituted by deuterium6-20An aryl group; or C comprising 1 heteroatom of N, O and S, unsubstituted or substituted by deuterium2-20A heteroaryl group.
Preferably, R4May be deuterium, C unsubstituted or substituted by deuterium6-20Aryl, carbazolyl unsubstituted or substituted with deuterium, phenylcarbazolyl unsubstituted or substituted with deuterium, dibenzofuranyl unsubstituted or substituted with deuterium, or dibenzothiophenyl unsubstituted or substituted with deuterium.
More preferably, R4May be deuterium, phenyl unsubstituted or substituted with deuterium, carbazolyl unsubstituted or substituted with deuterium, phenylcarbazolyl unsubstituted or substituted with deuterium, dibenzofuranyl unsubstituted or substituted with deuterium, or dibenzothiophenyl unsubstituted or substituted with deuterium.
For example, R4May be deuterium, or may be selected from any one of the following groups, but is not limited thereto:
Figure BDA0003002851710000711
preferably, d may be 0,1, 2 or 10. When d is 10, R4May be deuterium.
Specifically, for example, in the above chemical formulas 2-1 to 2-5, e is 0,1 or 4, f is 0,1 or 2, and g may be 0,1 or 4. When e is 4, f is 2, and g is 4, R4May be deuterium.
In addition, in the above chemical formulas 2-1 to 2-5, e + f + g is the same as d, and thus e + f + g may be 0,1, 2 or 10.
Representative examples of the compound represented by the above chemical formula 2 are as follows:
Figure BDA0003002851710000721
Figure BDA0003002851710000731
Figure BDA0003002851710000741
Figure BDA0003002851710000751
Figure BDA0003002851710000761
Figure BDA0003002851710000771
Figure BDA0003002851710000781
Figure BDA0003002851710000791
Figure BDA0003002851710000801
Figure BDA0003002851710000811
Figure BDA0003002851710000821
Figure BDA0003002851710000831
Figure BDA0003002851710000841
Figure BDA0003002851710000851
Figure BDA0003002851710000861
Figure BDA0003002851710000871
on the other hand, as an example, the compound represented by the above chemical formula 2 can be produced by a production method shown in the following reaction formula 2. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 2]
Figure BDA0003002851710000872
In the above reaction formula 2, X "is a halogen, preferably bromine or chlorine, and the definition of other substituents is the same as that described above.
Specifically, the compound represented by the above chemical formula 2 is produced by combining the starting materials B1 and B2 through an amine substitution reaction. Each of such amine substitution reactions is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the amine substitution reaction may be appropriately changed, and the method for producing the compound represented by chemical formula 2 may be further embodied in the production examples described below.
In addition, the first compound and the second compound may be contained in the light-emitting layer at a weight ratio of 1:9 to 9: 1. When the first compound is contained in the light-emitting layer too little, electron transfer in the light-emitting layer is not smooth, and the balance between holes and electrons in the entire device is not balanced, and therefore, there is a problem in voltage, efficiency, and lifetime of the manufactured device. For example, in the light-emitting layer, the weight ratio of the first compound to the second compound may be 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, or 4:6 to 5: 5.
On the other hand, the light-emitting layer may contain a dopant substance in addition to the 2 host substances. Examples of such dopant substances include aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Figure BDA0003002851710000881
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
In this case, the dopant substance may be contained in the light-emitting layer in an amount of 1 to 25 wt% based on the total weight of the host substance (the sum of the weight of the compound represented by chemical formula 1 and the weight of the compound represented by chemical formula 2) and the dopant substance.
Hole blocking layer
The organic light emitting device according to the present invention is formed as desiredA hole blocking layer may be included between the light emitting layer and an electron transport layer described later. The hole blocking layer is a layer formed on the light emitting layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the electron mobility, preventing excessive hole migration, and increasing the hole-electron binding ratio. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include triazine-containing azine derivatives, triazole derivatives, and the like,
Figure BDA0003002851710000882
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
Electron transport layer
The electron transport layer is formed between the light emitting layer and the cathode, and functions to receive electrons from the electron injection layer and transport the electrons to the light emitting layer. The electron transport layer contains an electron transport material, and such an electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material having a high mobility to electrons.
Specific examples of the electron injecting and transporting substance include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Figure BDA0003002851710000891
Azole,
Figure BDA0003002851710000892
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
Electron transport and injection layer
The organic light emitting device according to the present invention may include an electron injection layer between the electron transport layer and the cathode as necessary. Alternatively, the above organic light emitting device may include an electron transporting and injecting layer as necessary.
The electron transport and injection layer is a layer that injects electrons from the electrode, transports the received electrons to the light-emitting layer, and functions as an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injecting and transporting substance is a substance that favorably receives electrons from the cathode and transfers them to the light-emitting layer, and is suitable for a substance having a high mobility to electrons. Specific examples of the electron injecting and transporting substance include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Figure BDA0003002851710000893
Azole,
Figure BDA0003002851710000894
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
The electron transporting and injecting layer may be formed as a separate layer such as an electron injecting layer and an electron transporting layer. In this case, an electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport material described above can be used as the electron transport material contained in the electron transport layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, NaCl, CsF, Li, or the like can be used as an electron injection substance contained in the electron injection layer2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Figure BDA0003002851710000895
Azole,
Figure BDA0003002851710000896
Oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
Organic light emitting device
Fig. 1 illustrates a structure of an organic light emitting device according to the present invention. Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the above-described first compound and the above-described second compound may be contained in the above-described light-emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 8, and a cathode 4. In the structure as described above, the above-described first compound and the above-described second compound may be contained in the above-described light-emitting layer.
The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described constitutions. In this case, the following production can be performed: the anode is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method, and then the above layers are formed on the anode, and then a substance which can be used as a cathode is deposited thereon. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device. In addition, the host and the dopant can be formed by a solution coating method as well as a vacuum evaporation method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
On the other hand, the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
The fabrication of the above-described organic light emitting device is specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ Synthesis examples ]
Synthesis example 1: synthesis of Compound 1-1
Figure BDA0003002851710000911
Step 1) Synthesis of Compound 1-1-a
2-bromo-5-chlorophenol (20g, 96.4mmol) and (2, 6-difluorophenyl) boronic acid (15.2g, 96.4mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, sodium carbonate (30.7g, 289.2mmol) was dissolved in 31ml of water and added, and after sufficiently stirring, tetrakis (triphenyl-phosphine) palladium (3.3g, 2.9mmol) was added. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. The obtained product was again added to and dissolved in 20-fold 464mL of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce white1-1-a (16.5g, 71%, MS: [ M + H ]]+＝241.6)。
Step 2) Synthesis of Compound 1-1-b
1-1-a (15g, 62.3mmol) and 0(15.2g, 62.3mmol) and potassium carbonate (25.8g, 187mmol) were added to 300ml of dimethylformamide, stirred and refluxed. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 30-fold 413mL of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to give 1-1-b (10.7g, 78%, MS: [ M + H ]: as a white solid]+＝221.6)。
Step 3) Synthesis of Compound 1-1-c
Under nitrogen, 1-1-b (20g, 90.6mmol) and bis (pinacolato) diboron (23g, 90.6mmol) were added to 400ml of bis
Figure BDA0003002851710000921
In an alkane (Diox), stirred and refluxed. Then, potassium triphosphate (57.7g, 271.9mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone (1.6g, 2.7mmol) and tricyclohexylphosphine (1.5g, 5.4mmol) were added. After reacting for 2 hours, the reaction mixture was cooled to normal temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was again added to 10-fold 283mL of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give 1-1-c (22.6g, 80%, MS: [ M + H ]: as a brown solid]+＝313.2)。
Step 4) Synthesis of Compound 1-1-d
Under nitrogen atmosphere, 1-c (20g, 64.1mmol) and 2-chloro-4- (dibenzo [ b, d ]]Furan-1-yl) -6-phenyl-1, 3, 5-triazine (22.9g, 64.1mmol) was added to 400ml of tetrahydrofuran, stirred and refluxed. Then, sodium carbonate (20.4g, 192.2mmol) was dissolved in 20ml of water and added thereto, followed by well stirring, and then tetrakis (tris (phosphonium)) was addedPhenyl-phosphine) palladium (2.2g, 1.9 mmol). After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. The obtained product was again added to and dissolved in 20 times 647mL of chloroform, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give 1-1-d (22.3g, 69%, MS: [ M + H ]: as a yellow solid]+＝505.6)。
Step 5) Synthesis of Compound 1-1
1-d (15g, 29.7mmol) and 9H-carbazole-1, 2,3,4,5,6,7,8-d8(5.2g, 29.7mmol) were added to 300ml of dimethylformamide under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (12.3g, 89.2mmol) was added, and the mixture was heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 30-fold 591mL of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to give compound 1(11.4g, 58%, MS: [ M + H ]: as a yellow solid]+＝663.8)。
Synthesis example 2: synthesis of Compound 1-2
Figure BDA0003002851710000931
In Synthesis example 1, 2-chloro-4- (dibenzo [ b, d ]]Compound 1-2 (MS: [ M + H ]]+＝662.3)。
Synthesis example 3: synthesis of Compounds 1-3
Figure BDA0003002851710000941
In Synthesis example 1, 2-bromo was reacted with-5-chlorophenol, 2-chloro-4- (dibenzo [ b, d ]]Except that furan-3-yl) -1-phenyl-1, 3, 5-triazine and 9H-carbazole-1, 2,3,4,5,6,7,8-d8 were respectively changed to 2-bromo-6-chlorophenol, 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole for use, compound 1-3(MS [ M + H ] was produced by the same production method as compound 1-1]+＝646.2)。
Synthesis example 4: synthesis of Compounds 1-4
Figure BDA0003002851710000951
In Synthesis example 1, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Compound 1-4(MS [ M + H) was produced by the same production method as that of compound 1-1 except that furan-3-yl) -6-phenyl-1, 3, 5-triazine was used instead of (2, 5-difluorophenyl) boronic acid and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, respectively]+＝573.2)。
Synthesis example 5: synthesis of Compounds 1-5
Figure BDA0003002851710000961
Compound 1-5(MS [ M + H) was produced by the same production method as that of compound 1-1 except that 2-bromo-5-chlorophenol and (2, 6-difluorophenyl) boronic acid were used instead of 2-bromo-3-chlorophenol and (2, 5-difluorophenyl) boronic acid, respectively, in synthesis example 1]+＝663.2)。
Synthesis example 6: synthesis of Compounds 1-6
Figure BDA0003002851710000971
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid, 2-chloro-4- (dibenzo [ b, d ] is used]Furan-3-yl) -6-phenyl-1, 3, 5-triazine and 9H-carbazole-1, 2,3,4,5,6,7,8-d8 were changed to 2-bromo-3-chlorophenol, (2, 4-difluorophenyl) boronic acid, 2-chloro-4, 6-diphenyl, respectivelyCompound 1-6(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that-1, 3, 5-triazine and 4- (phenyl-d 5) -9H-carbazole were used]+＝646.2)。
Synthesis example 7: synthesis of Compounds 1-7
Figure BDA0003002851710000981
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Furan-1-yl) -6-phenyl-1, 3, 5-triazine to 2-bromo-3-chlorophenol, (2, 4-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] respectively]Compound 1-7(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that furan-4-yl) -6-phenyl-1, 3, 5-triazine was used]+＝663.2)。
Synthesis example 8: synthesis of Compounds 1-8
Figure BDA0003002851710000991
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Furan-3-yl) -6-phenyl-1, 3, 5-triazine to 2-bromo-3-chlorophenol, (2, 4-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] respectively]Compound 1-8(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that furan-1-yl) -6-phenyl-1, 3, 5-triazine was used]+＝663.2)。
Synthesis example 9: synthesis of Compounds 1-9
Figure BDA0003002851710001001
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid, 2-chloro-4- (dibenzo [ b, d ] is used]Furan-3-yl) -6-phenyl-1, 3, 5-triazine and 9H-carbazole-1, 2,3,4,5,6,7,8-d8 are changed to 2-bromo-3-chloro-6-chlorophenol, (2-fluoro) boronic acid, respectively,Compound 1-9(MS [ M + H ] was produced by the same production method as that for compound 1-1, except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 4- (phenyl-d 5) -9H-carbazole were used]+＝646.2)。
Synthesis example 10: synthesis of Compounds 1-10
Figure BDA0003002851710001011
In Synthesis example 1, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are used]Except that furan-1-yl) -6-phenyl-1, 3, 5-triazine and 9H-carbazole-1, 2,3,4,5,6,7,8-d8 were respectively changed to (2, 4-difluorophenyl) boronic acid, 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 3-phenyl-9H-carbazole for use, compounds 1 to 10(MS [ M + H ] was produced by the same production method as that of compound 1-1 (MS [ M + H ] s-t-e)]+＝646.2)。
Synthesis example 11: synthesis of Compounds 1-11
Figure BDA0003002851710001021
In Synthesis example 1, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Conversion of furan-3-yl) -6-phenyl-1, 3, 5-triazine to (2, 3-difluorophenyl) boronic acid and 2- ([1,1' -biphenyl, respectively]Compound 1-11(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that (E) -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used]+＝648.2)。
Synthesis example 12: synthesis of Compounds 1-12
Figure BDA0003002851710001031
In Synthesis example 1, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Conversion of furan-3-yl) -6-phenyl-1, 3, 5-triazine to (2, 3-difluorophenyl) boronic acid and 2- ([1,1' -biphenyl, respectively]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine, and in addition thereto, by neutralizationProduction method of Compound 1-1 Compound 1-12(MS [ M + H ]]+＝648.2)。
Synthesis example 13: synthesis of Compounds 1-13
Figure BDA0003002851710001041
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Furan-3-yl) -6-phenyl-1, 3, 5-triazine to 2-bromo-3-chlorophenol, (2, 3-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] respectively]Compound 1-13(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine was used]+＝679.2)。
Synthesis example 14: synthesis of Compounds 1-14
Figure BDA0003002851710001051
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid, 2-chloro-4- (dibenzo [ b, d ] is used]Except that furan-3-yl) -6-phenyl-1, 3, 5-triazine and 9H-carbazole-1, 2,3,4,5,6,7,8-d8 were respectively changed to 2-bromo-3-chlorophenol, (2, 3-difluorophenyl) boronic acid, 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole for use, compounds 1 to 14(MS [ M + H-carbazole) were produced by the same production method as that of compound 1 to 1]+＝646.2)。
Synthesis example 15: synthesis of Compounds 1-15
Figure BDA0003002851710001061
In Synthesis example 1, 2-bromo-5-chlorophenol, (2, 6-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] are reacted]Furan-3-yl) -6-phenyl-1, 3, 5-triazine to 2-bromo-3-chlorophenol, (2, 3-difluorophenyl) boronic acid and 2-chloro-4- (dibenzo [ b, d ] respectively]Furan-1-yl) -6-phenyl-1, 3, 5-triazinesCompound 1-15(MS [ M + H ] was produced by the same production method as that for Compound 1-1, except that 9H-carbazole-1, 2,3,4,5,6,7,8-d8 was used]+＝663.2)。
Synthesis example 16: synthesis of Compound 2-1
Figure BDA0003002851710001071
Step 1) Synthesis of Compound 2-1-a
Under nitrogen atmosphere, reacting 11, 12-indolino [2,3-a ]]Carbazole (30g, 117mmol) and bromobenzene (18.4g, 117mmol) were added to 600ml of toluene, stirred and refluxed. Then, sodium tert-butoxide (33.8g, 351.1mmol) was added, and after stirring well, bis (tri-tert-butylphosphino) palladium (1.8g, 3.5mmol) was added. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was again added to 10 times 389mL of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to give 2-1-a (30g, 77%, MS: [ M + H ]: as a yellow solid]+＝333.4)。
Step 2) Synthesis of Compound 2-1
2-1-a (30g, 90.2mmol) and 4-chloro-1, 1':3',1 "-terphenyl-2", 3 ", 4", 5 ", 6" -d5(23.2g, 90.2mmol) were added to 600ml of toluene under nitrogen, stirred and refluxed. Then, sodium tert-butoxide (26g, 270.7mmol) was added, and after stirring well, bis (tri-tert-butylphosphino) palladium (1.4g, 2.7mmol) was added. After 4 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was again added to and dissolved in 10 times 511mL of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to produce a white solid compound2-1(39.3g，77％，MS:[M+H]+＝566.7)。
Synthesis example 17: synthesis of Compound 2-2
Figure BDA0003002851710001081
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 7-indolino [2,3-b ] respectively]Compound 2-2(MS [ M + H ] was produced by the same production method as that for Compound 2-1 except that carbazole, 4-chloro-1, 1' -biphenyl-2 ',3',4',5',6' -d5 and 3-chloro-1, 1':4', 1' -terphenyl were used]+＝642.8)。
Synthesis example 18: synthesis of Compounds 2-3
Figure BDA0003002851710001091
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 8-indolino [2,3-c ] respectively]Compound 2-3(MS [ M + H ] was produced by the same production method as that for Compound 2-1 except that carbazole, 4-chloro-1, 1 '-biphenyl and 4-chloro-1, 1':3', 1' -terphenyl were used]+＝637.3)。
Synthesis example 19: synthesis of Compounds 2-4
Figure BDA0003002851710001092
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 8-indolino [2,3-c ] respectively]Compound 2-4(MS [ M + H ] was produced by the same production method as that for Compound 2-1, except that carbazole-1, 2,3,4,6,7,9,10,11,12-d10 was used]+＝561.2)。
Synthesis example 20: synthesis of Compounds 2-5
Figure BDA0003002851710001101
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 8-indolino [2,3-c ] respectively]Carbazole, 3-bromodibenzo [ b, d ]]Compound 2-5(MS [ M + H ] was produced by the same production method as that for Compound 2-1, except that furan and 4-chloro-1, 1 '-biphenyl-2', 3',4',5',6' -d5 were used]+＝580.2)。
Synthesis example 21: synthesis of Compounds 2-6
Figure BDA0003002851710001111
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 11-indolino [3,2-b ] respectively]Compound 2-6(MS [ M + H ] was produced by the same production method as that for compound 2-1, except that carbazole and 3-bromo-1, 1' -biphenyl were used]+＝561.2)。
Synthesis example 22: synthesis of Compounds 2-7
Figure BDA0003002851710001112
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 12-indolino [3,2-a ] respectively]Compound 2-7(MS [ M + H ] was produced by the same production method as that for compound 2-1, except that carbazole and 4-bromo-1, 1' -biphenyl were used]+＝561.2)。
Synthesis example 23: synthesis of Compounds 2 to 8
Figure BDA0003002851710001121
In Synthesis example 16, 11, 12-indolino [2,3-a ] was reacted]Carbazole, bromobenzene and 4-chloro-1, 1':3',1 '-terphenyl-2', 3',4',5',6' -d5 to 5, 7-indolino [2,3-b ] respectively]Compound 2-7(MS [ M + H ] was produced by the same production method as that for Compound 2-1, except that carbazole and bromobenzene were used]+＝561.2)。
[ examples ]
Example 1
Indium Tin Oxide (ITO) and a process for producing the same
Figure BDA0003002851710001122
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HT-A compound and the following PD compound were mixed in a weight ratio of 95:5
Figure BDA0003002851710001123
Is subjected to thermal vacuum evaporation to form a hole injection layer, and then only the following HT-A compound is added
Figure BDA0003002851710001124
The hole transport layer is formed by evaporation. On the above hole transport layer, the following HT-B compound
Figure BDA0003002851710001125
The electron blocking layer (electron inhibiting layer) is formed by thermal vacuum deposition.
On the electron blocking layer, the compound 1-1 and the compound 2-1 produced above as host compounds and the following GD compound as dopant compounds were mixed in a weight ratio of 85:15
Figure BDA0003002851710001126
The thickness of (2) is vacuum-evaporated to form a light-emitting layer. In this case, the weight ratio of the compound 1-1 to the compound 2-1 is 1: 1.
On the light-emitting layer, the following ET-A compound is added
Figure BDA0003002851710001127
The hole blocking layer is formed by vacuum evaporation. On the hole-blocking layer, the following ET-B compound and the following Liq compound are mixed in a weight ratio of 2:1
Figure BDA0003002851710001128
Is subjected to thermal vacuum evaporation, and then LiF and magnesium are mixed in a weight ratio of 1:1
Figure BDA0003002851710001132
Is vacuum evaporated to form an electron transporting and injecting layer. On the above electron transporting and injecting layer, magnesium and silver were mixed in a weight ratio of 1:4
Figure BDA0003002851710001133
The cathode is formed by vapor deposition to produce an organic light-emitting device.
Figure BDA0003002851710001131
In the above process, the evaporation speed of the organic material is maintained
Figure BDA0003002851710001134
Lithium fluoride maintenance of cathode
Figure BDA0003002851710001136
Deposition rate of (3), silver and magnesium maintenance
Figure BDA0003002851710001135
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Examples 2 to 15
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the compound described in table 1 below was used instead of compound 1.
At this time, the structures of the compounds used in examples are arranged as follows.
Figure BDA0003002851710001141
Figure BDA0003002851710001151
Figure BDA0003002851710001161
Comparative examples 1 to 7
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the compound described in table 1 below was used instead of compound 1.
In this case, in Table 1 below, the compounds H-2 and C1 are shown below.
Figure BDA0003002851710001162
Examples
For the above-mentioned embodimentsThe voltage, efficiency, and lifetime (T95) of the organic light-emitting devices produced in the comparative examples were measured by applying a current thereto, and the results are shown in table 1 below. At this time, the voltage and efficiency were 10mA/cm2Is measured by the current density of (a). Furthermore, T95 in Table 1 below indicates a current density of 20mA/cm2Next, the time measured when the initial brightness decreased to 95%.
[ Table 1]
Figure BDA0003002851710001181
Figure BDA0003002851710001191
As shown in table 1 above, it is understood that the organic light emitting devices of examples in which all of the first compound and the second compound of the present invention are used as the main components exhibit superior characteristics in terms of efficiency and lifetime as compared with the organic light emitting devices of comparative examples 1 to 3 in which only the first compound is used and the organic light emitting devices of comparative examples 4 and 5 in which neither of the first compound and the second compound is used.
In addition, it is understood that although the organic light emitting device of the above embodiment uses 2 kinds of hosts, it also exhibits high efficiency and excellent lifetime as compared with the organic light emitting devices of comparative examples 6 and 7 in which a combination of other hosts is used instead of the combination of the above first compound and second compound.
This means that, considering that the light emission efficiency and the life time characteristics of a general organic light emitting device have a Trade-off relationship with each other, the organic light emitting device using the compound of the present invention shows significantly improved device characteristics as compared with the comparative example device.
[ description of symbols ]
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: hole blocking layer
9: an electron transport and injection layer.

Claims (17)

1. An organic light emitting device, comprising: an anode;
a cathode provided to face the anode; and
a light-emitting layer between the anode and the cathode,
the light emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:
chemical formula 1
Figure FDA0003002851700000011
In the chemical formula 1, the first and second organic solvents,
x is O or S, and X is O or S,
X1to X3Each independently is N or CH, provided that X1To X3At least one of which is N,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
R1to R3Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
a + b is an integer of 0 to 6,
c is an integer of 0 to 8,
chemical formula 2
Figure FDA0003002851700000012
In the chemical formula 2,
a is a benzene ring condensed with two adjacent five-membered rings,
Ar3and Ar4Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
R4is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60Heteroaryl, and
d is an integer of 0 to 10.
2. The organic light emitting device of claim 1, wherein Ar1And Ar2At least one of which is C substituted by deuterium6-60An aryl group; or C substituted by deuterium containing 1 or more heteroatoms selected from N, O and S2-60Heteroaryl, or
R1To R3At least one of which is deuterium; c substituted by deuterium6-60An aryl group; or C substituted by deuterium containing 1 or more heteroatoms selected from N, O and S2-60Heteroaryl, a + b + c is 1 or more.
3. The organic light emitting device according to claim 1, wherein the first compound is represented by any one of the following chemical formulas 1A 'to 1E':
chemical formula 1A'
Figure FDA0003002851700000021
Chemical formula 1B'
Figure FDA0003002851700000031
Chemical formula 1C'
Figure FDA0003002851700000032
Chemical formula 1D'
Figure FDA0003002851700000033
Chemical formula 1E'
Figure FDA0003002851700000034
In the chemical formulas 1A 'to 1E',
X、X1to X3、Ar1、Ar2、R1To R3A + b and c are as defined in claim 1.
4. An organic light-emitting device according to claim 1 wherein X is O.
5. The organic light emitting device of claim 1, wherein X1To X3Are all N, or
X1And X2Is N, X3Is CH, or
X1And X3Is N, X2Is CH, or
X1Is N, X2And X3Is CH, or
X2Is N, X1And X3Is CH.
6. The organic light emitting device of claim 1, wherein Ar1And Ar2Each independently is phenyl, biphenyl, naphthyl, phenanthryl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzo
Figure FDA0003002851700000042
An azole group or a benzothiazolyl group,
wherein Ar is1And Ar2Unsubstituted or substituted by deuterium, C1-10Alkyl and C6-20And 1 or more substituents in the aryl group.
7. The organic light emitting device of claim 1, wherein Ar1And Ar2Each independently is any one selected from the following groups:
Figure FDA0003002851700000041
Figure FDA0003002851700000051
in the above-mentioned group, the group,
m is an integer of 0 to 7.
8. The organic light emitting device of claim 1, wherein R1And R2Each independently is hydrogen, deuterium, phenyl substituted with 1 to 5 deuterium, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.
9. The organic light emitting device of claim 1, wherein R3Is hydrogen, deuterium, phenyl unsubstituted or substituted by deuterium, carbazolyl unsubstituted or substituted by deuterium, dibenzofuranyl unsubstituted or substituted by deuterium, or dibenzothiophenyl unsubstituted or substituted by deuterium.
10. The organic light emitter of claim 1Wherein said substituent is
Figure FDA0003002851700000052
Is any one of substituents represented by the following chemical formulae 3a to 3 i:
Figure FDA0003002851700000061
in the chemical formulas 3a to 3i,
p is an integer of 0 to 7, and
q is an integer of 0 to 8.
11. The organic light emitting device of claim 1,
a + b is 0,1, 2 or 6,
c is 0,1, 2 or 8.
12. The organic light-emitting device according to claim 1, wherein the first compound is any one selected from the group consisting of:
Figure FDA0003002851700000071
Figure FDA0003002851700000081
Figure FDA0003002851700000091
Figure FDA0003002851700000101
Figure FDA0003002851700000111
Figure FDA0003002851700000121
Figure FDA0003002851700000131
Figure FDA0003002851700000141
Figure FDA0003002851700000151
Figure FDA0003002851700000161
Figure FDA0003002851700000171
Figure FDA0003002851700000181
Figure FDA0003002851700000191
Figure FDA0003002851700000201
Figure FDA0003002851700000211
Figure FDA0003002851700000221
Figure FDA0003002851700000231
Figure FDA0003002851700000241
Figure FDA0003002851700000251
Figure FDA0003002851700000261
Figure FDA0003002851700000271
Figure FDA0003002851700000281
Figure FDA0003002851700000291
Figure FDA0003002851700000301
Figure FDA0003002851700000311
Figure FDA0003002851700000321
Figure FDA0003002851700000331
Figure FDA0003002851700000341
Figure FDA0003002851700000351
Figure FDA0003002851700000361
Figure FDA0003002851700000371
Figure FDA0003002851700000381
Figure FDA0003002851700000391
Figure FDA0003002851700000401
Figure FDA0003002851700000411
Figure FDA0003002851700000421
Figure FDA0003002851700000431
Figure FDA0003002851700000441
Figure FDA0003002851700000451
Figure FDA0003002851700000461
Figure FDA0003002851700000471
Figure FDA0003002851700000481
Figure FDA0003002851700000491
Figure FDA0003002851700000501
Figure FDA0003002851700000511
Figure FDA0003002851700000521
Figure FDA0003002851700000531
Figure FDA0003002851700000541
13. the organic light-emitting device according to claim 1, wherein the second compound is represented by any one of the following chemical formulas 2-1 to 2-5:
chemical formula 2-1
Figure FDA0003002851700000542
Chemical formula 2-2
Figure FDA0003002851700000551
Chemical formula 2-3
Figure FDA0003002851700000552
Chemical formula 2-4
Figure FDA0003002851700000553
Chemical formula 2-5
Figure FDA0003002851700000554
In the chemical formulas 2-1 to 2-5,
R4each independently is deuterium; substituted or unsubstituted C6-20An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-20(ii) a heteroaryl group, wherein,
e is an integer of 0 to 4,
f is an integer of 0 to 2,
g is an integer of 0 to 4, and
Ar3and Ar4As defined in claim 1.
14. The organic light emitting device of claim 1, wherein Ar3And Ar4Each independently of the others is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, dibenzofuranyl or dibenzothiophenyl,
wherein Ar is3And Ar4Unsubstituted or substituted with 1 or more substituents selected from deuterium, phenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl and dibenzothiophenyl.
15. The organic light emitting device of claim 1, wherein R4Is deuterium, phenyl unsubstituted or substituted by deuterium, carbazolyl unsubstituted or substituted by deuterium, phenylcarbazolyl unsubstituted or substituted by deuterium, dibenzofuranyl unsubstituted or substituted by deuterium, or dibenzothiophenyl unsubstituted or substituted by deuterium.
16. An organic light-emitting device according to claim 1 wherein d is 0,1, 2 or 10.
17. The organic light-emitting device according to claim 1, wherein the second compound is any one selected from the group consisting of:
Figure FDA0003002851700000571
Figure FDA0003002851700000581
Figure FDA0003002851700000591
Figure FDA0003002851700000601
Figure FDA0003002851700000611
Figure FDA0003002851700000621
Figure FDA0003002851700000631
Figure FDA0003002851700000641
Figure FDA0003002851700000651
Figure FDA0003002851700000661
Figure FDA0003002851700000671
Figure FDA0003002851700000681
Figure FDA0003002851700000691
Figure FDA0003002851700000701
Figure FDA0003002851700000711
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