CN115304497A - Fluorene derivative containing homotriptycene and application thereof - Google Patents
Fluorene derivative containing homotriptycene and application thereof Download PDFInfo
- Publication number
- CN115304497A CN115304497A CN202211064801.5A CN202211064801A CN115304497A CN 115304497 A CN115304497 A CN 115304497A CN 202211064801 A CN202211064801 A CN 202211064801A CN 115304497 A CN115304497 A CN 115304497A
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- substituted
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- fluorene derivative
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- 125000001769 aryl amino group Chemical group 0.000 claims description 8
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- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 4
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to a fluorene derivative containing homotriptycene and application thereof in an organic electroluminescent element. The structure of the fluorene derivative containing homotriptycene is shown as a formula (I), and the fluorene derivative has homotriptycene and spirofluorene structures; the fluorene derivative is applied to an organic electroluminescent element, so that the driving voltage can be obviously reduced, the luminous efficiency can be improved, and the service life can be prolonged;
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a fluorene derivative containing homotriptycene, an organic material and application thereof in an organic electroluminescent element.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer; when the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, organic electroluminescent display technologies have become mature, some products have entered the market, but many problems still need to be solved in the industrialization process. In particular, various organic materials used for manufacturing elements have many problems which are not solved, such as carrier injection and transmission performance, electroluminescent performance of the materials, service life, color purity, matching between various materials and between various electrodes, and the like; especially, the luminous efficiency and the service life of the light emitting element do not meet the practical requirements, which greatly limits the development of the OLED technology. The metal complex phosphorescent material utilizing triplet state luminescence has high luminous efficiency, and green and red light materials of the metal complex phosphorescent material meet the use requirements, but the metal complex phosphorescent material requires a phosphorescent material or a hole material with a high triplet state energy level to be matched with the metal complex phosphorescent material, so that the development of the phosphorescent material or the hole material with the high triplet state energy level is an urgent need for the development of the current OLED.
Under the current technological development, improvements are also needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent elements and thermal stability during sublimation.
Accordingly, in order to overcome the above-described problems of the conventional techniques and to further improve the characteristics of the organic electroluminescent element, development of a more stable and effective substance which can be used as a phosphorescent material or a hole-forming material in the organic electroluminescent element is continuously required.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a fluorene derivative which contains a high triptycene structure, and an organic electroluminescent element prepared by using the fluorene derivative can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life; another object of the present invention is to provide an application of the fluorene derivative in an organic electroluminescent element.
Specifically, the invention provides the following technical scheme:
the invention provides a fluorene derivative, the structural formula of which is shown as the formula (I):
wherein the content of the first and second substances,
R 1 ～R 5 each independently selected from hydrogen, deuterium, C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heteroaryl or a group of formula (II);
x, y, z, n and m are independently selected from integers of 0-4;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
w is an integer from 0 to 5;
l is selected from single bond, substituted or unsubstituted C 6 -C 60 Or substituted or unsubstituted C 2 -C 60 Heteroarylene group;
* -represents R 1 ～R 5 The position of bonding to L.
In the present invention, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring formed by bonding adjacent groups to each other.
Preferably, said aryl, heteroaryl, in particular refers to groups derived from: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl,
A perylene group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group,Terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-indenocarbazolyl, cis-or trans-indonocarbazolyl, triindenyl, isotridecyl, spirotriindenyl, spiroisotridecyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo [5,6,6]Quinolyl, benzo [6,7 ]]Quinolyl, benzo [7,8 ]]Quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthrenyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthryl, 2, 7-diazapyranyl, 2, 3-diazapyranyl, 1, 6-diazapyranyl, 1, 8-diazapyranyl, 4,5,9, 10-tetraazapyrylpropenyl, pyrazinyl phenazinyl, phenoxazinyl, phenothiazinyl, fluorerynyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, carbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, phenothiazinyl, benzoquinazolinyl, benzothiadiazolyl, or a combination of these groups derived from these systems.
Preferably, R is 1 Is a group shown in formula (II), and x is 1; and/or R 2 Is a group of formula (II), y is 1; and/or R 3 Is a group of formula (II), z is 1; and/or R 4 Is a formula of(II) and n is 1; and/or R 5 Is a group shown in formula (II), and m is 1.
Preferably, R is 1 ～R 5 Each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, t-butyl, nitrile, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
Preferably, w is 0, 1 or 2.
Preferably, said R is 1 ～R 5 At least one of them is a group represented by the formula (II); and R is 1 ～R 5 Each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, t-butyl, nitrile, substituted or unsubstituted carbazolyl.
Preferably, ar is 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
Preferably, the L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted fluorenylene group, and a substituted or unsubstituted carbazolyl group.
Further, the L is selected from a single bond or a group consisting of the following groups III-1 to III-16:
wherein the content of the first and second substances,
Z 11 、Z 12 each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C 1 -C 60 Alkyl of (C) 2 -C 60 Alkenyl of (C) 2 -C 60 Alkynyl of (A), C 1 -C 60 Alkoxy group of (C) 3 -C 60 A cycloalkane group of 3 -C 60 With cycloalkenyl radicals, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylsulfonyl ether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylsulfonyl ether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 1 represents O, S, CR ' R ' or NAr ';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 -C 60 Alkyl of (C) 1 -C 60 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groupsR 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 -C 60 Alkyl of (C) 1 -C 60 Heteroalkyl of (a), C 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, ar' is methyl, ethyl, phenyl or naphthyl;
The term "substituted or unsubstituted" as used herein means a group selected from the group consisting of hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, and C 1 -C 40 Alkyl of (C) 2 -C 40 Alkenyl of, C 2 -C 40 Alkynyl of (A), C 1 -C 40 Alkoxy group of (C) 3 -C 40 Cycloalkyl of, C 3 -C 40 Cycloalkenyl group of (1), C 6 -C 60 Aryl of (C) 6 -C 60 Aryloxy group of (1), C 6 -C 60 And C is an aryl sulfide group 2 -C 60 The heterocyclic aryl group of (1) is substituted or unsubstituted or substituted or unsubstituted with a substituent in which 2 or more substituents among the above-exemplified substituents are bonded.
Preferably, the structural formula of the fluorene derivative is selected from the group consisting of C602 to C772 below:
wherein, T 2 -is selected from-O-, -S-, or one of the following structures:
* -and-represent a connecting bond.
The invention provides a synthetic route of a compound shown as a formula (I), which is shown as follows:
wherein X represents I, br, cl or OTf; the other symbols used are as defined above.
The raw materials for synthesizing the compound shown in the formula (I) can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and other means are well known by the synthesizers in the field, and the synthesis process can be completely realized to obtain the target product.
Specifically, the compound of the formula (I) is prepared by carrying out substitution reaction, oxidation reaction, condensation reaction, SUZUKI coupling, buchwald-Hartwig coupling and other reactions on substituted benzene homoptera-pterene. Ar (Ar) 1 Ar 2 N-(L) w B(OH) 2 Or Ar 1 Ar 2 The NH is prepared by a palladium-catalyzed or base-catalyzed coupling reaction.
As palladium catalysts which can be used for the palladium-catalyzed coupling reaction, there may be selected: pd (P- t Bu 3 ) 2 、Pd(PPh 3 ) 4 、Pd 2 (dba) 3 、Pd 2 (dba) 3 CHCl 3 、PdCl 2 (PPh 3 ) 2 、PdCl 2 (CH 3 CN) 2 、Pd(OAc) 2 、Pd(acac) 2 、Pd/C、PdCl 2 、[Pd(allyl)Cl] 2 And the like, or a mixture of two or more thereof is used.
In addition, the base used in the palladium-catalyzed coupling reaction or base-catalyzed coupling reaction may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and mixtures of one or two or more thereof.
The coupling reaction may be carried out in an organic solvent, wherein the organic solvent may be selected from: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, or anisole, aromatic hydrocarbon solvents such as benzene, toluene, or xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and one or a mixture of two or more thereof may be used.
The invention also provides an organic electroluminescent material, the raw material of which comprises the fluorene derivative; the organic electroluminescent material comprising the fluorene derivative of the present invention has carrier transporting ability or light extracting ability.
Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a light extraction layer material, or an electron blocking layer material.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a light extraction layer, and one or more organic layers disposed between the first electrode and the second electrode; at least one of the organic layer and the light extraction layer includes the fluorene derivative described above.
The organic electroluminescent element includes a first electrode, a second electrode, a light extraction layer, and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, functional layers, with both hole-transporting and electron-blocking functions, electron-transporting layers, electron-injecting layers, hole-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent element described herein may include one light-emitting layer, or it may include a plurality of light-emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particular preference is given to systems having three light-emitting layers, where the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, at least one of these layers comprises, according to the invention, a compound according to the invention.
Further, the organic electroluminescent element according to the invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light-emitting layer is directly adjacent to the hole injection layer or the anode and/or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and the light-emitting layer and in the light extraction layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process with a temperature of less than 10 ℃ in a vacuum sublimation apparatus -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers can also be applied by means of organic vapor deposition methods or by means of carrier gas sublimation, where 10 is -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Furthermore, organic electroluminescent elements are preferred in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermography, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, soluble compounds obtained by suitable substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to pharmaceutical compositions comprising at least one compound of the invention as indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. Processing of the compounds of the invention from the liquid phase, for example by spin coating or by printing processes, requires the processing of formulations of the compounds of the invention which may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchytone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol dibutyl glycol methyl ether, triethyl glycol, tripropyl glycol, 1, 2-dimethyl benzyl ether, 1, 2-octylbenzene glycol, 1, 2-dimethyl-octylbenzene ether, 1, octylbenzene glycol, or mixtures of these solvents.
The present invention also provides an application of an organic electroluminescence element using any one selected from the following devices:
a flat panel display device;
a flexible display device;
a monochromatic or white flat panel lighting device; or
A monochromatic or white flexible lighting device.
The invention has the following beneficial effects:
the fluorene derivative shown in the formula (I) contains a high triptycene structure, has high glass transition temperature thermal stability and excellent capacity of transporting holes and electrons, and molecules are easy to form a uniform thin film under a vacuum condition. When the fluorene derivative is applied to an organic electroluminescent element, the driving voltage can be obviously reduced, the luminous efficiency can be improved, and the service life can be prolonged.
Drawings
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic diagram of an organic light-emitting device 200 with two light-emitting layers. The device comprises a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships that are based on the orientations or positional relationships shown in the drawings, are merely for convenience in describing the present invention and to simplify the description, and do not indicate or imply that the referenced devices or elements must have a particular orientation, be constructed and operated in a particular orientation, and thus, are not to be construed as limiting the present invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The experimental raw materials and the related equipments used in the following examples are commercially available unless otherwise specified, and the percentages are by mass unless otherwise specified.
In addition, unless otherwise specified, any range recited herein includes any value between the endpoints and any sub-range defined by any value between the endpoints or any value between the endpoints.
The following test instruments and methods for performance testing of OLED materials and devices were used in the examples as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1
A method for preparing compound C748, comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
20.0mmol of 6-bromobenzohomotriptycene (prepared by the method disclosed in the reference patent CN 113651858A) is dissolved in 50mL of acetonitrile, 20.0mmol of hydrated copper sulfate and 60.0mmol of potassium persulfate are added, 50mL of water is added, the mixture is heated to reflux and stirred for reaction for 2 hours, the temperature is reduced to room temperature, 50mL of water is added, dichloromethane is used for extraction, an organic phase is collected, the organic phase is dried, reduced pressure concentration is carried out, and the mixture is separated and purified by a silica gel column to obtain a compound Int-1, a yellow solid, and the yield is as follows: 93 percent.
The second step: preparation of intermediate Int-2
Under the protection of nitrogen, 22.0mmol of 2-bromobiphenyl is dissolved in 50mL of dry THF, the temperature is reduced to-78 ℃, 24.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, the mixture is stirred and reacted for 10 minutes, 20.0mmol of Int-1 solution dissolved in THF is added dropwise, the mixture is stirred and reacted for 1 hour, the room temperature is raised, 20mL of saturated ammonium chloride aqueous solution is added, the organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected, dried and concentrated under reduced pressure to obtain yellow solid, the yellow solid is dissolved in 50mL of dry dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride ether solution is added, the mixture is stirred and reacted for 1 hour, the mixture is raised to the room temperature and reacted for 12 hours, 50mL of 5% sodium hydroxide aqueous solution is added, the organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected, dried, concentrated under reduced pressure to obtain dry, the compound Int-2 is separated and purified by a silica gel column to obtain compound Int-2, a white solid, and the yield: 83 percent.
With reference to the analogous synthetic procedures described above, the following compounds shown in table 1 were prepared:
TABLE 1
The third step: preparation of Compound C748
Under nitrogen protection, 22.0mmol of intermediate Int-2 was dissolved in 50mL of dry toluene, and 20.0mmol of diarylamine, 30.0mmol of sodium tert-butoxide, and 0.2mmol of Pd were added 2 (dba) 3 Adding 0.4mmol of XantPhos, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, extracting a water phase with toluene, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound C748;
T 2 ：CMe 2 white solid, yield: 85%, MS (MALDI-TOF): m/z =778.3482[ m ] +H] + ； 1 HNMR(δ、CDCl 3 )：8.09(1H,s)；7.89～7.86(4H,m)；7.52～7.48(3H,m)；7.43～7.27(15H,m)；7.19～7.10(8H,m)；7.06～7.02(2H,m)；6.95～6.92(2H,m)；4.92(1H,s)；4.78(1H,s)；1.68(6H,s)。
T 2 : FR (9, 9-fluorenyl), white solid, yield: 82%, MS (MALDI-TOF): m/z =900.3636[ 2 ] M + H] + ； 1 HNMR(δ、CDCl 3 )：8.09(1H,s)；7.89～7.83(6H,m)；7.54～7.49(3H,m)；7.46～7.35(13H,m)；7.33～7.27(7H,m)；7.19～7.10(9H,m)；7.06～7.02(2H,m)；6.95～6.92(2H,m)；4.92(1H,s)；4.78(1H,s)。
With reference to the analogous synthetic procedures described above, the following compounds shown in table 2 were prepared:
TABLE 2
Example 2
A process for the preparation of compound C647, comprising the steps of:
the first step is as follows: preparation of intermediate Int-3
20.0mmol of A5 are dissolved in 40mL of DMF under nitrogen protection, 22.0mmol of pinacol diboron, 30.0mmol of anhydrous potassium acetate, 30.0mmol of cuprous iodide and 0.2mmol of PdCl are added 2 (dppf), heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, pouring the reaction solution into 200mL of ice water, filtering, washing a filter cake with water, drying, and separating and purifying through a silica gel column to obtain a compound Int-3, namely a white solid, with the yield: 87 percent.
The second step: preparation of intermediate Int-4
Under the protection of nitrogen, 22.0mmol of intermediate Int-3 is dissolved in 40mL of toluene, 20.0mmol of p-bromoiodobenzene, 60.0mmol of sodium carbonate, 0.01mmol of Pd0132, 20mL of ethanol and 20mL of water are added, the temperature is raised to reflux and stirred for reaction for 12 hours, the reaction solution is cooled to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by toluene, the organic phase is combined and dried, the filtration is carried out, the filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column, so that a compound Int-4 is obtained, namely a white solid, and the yield is as follows: 85 percent.
The third step: preparation of Compound C647
Under nitrogen protection, 22.0mmol of intermediate Int-4 was dissolved in 50mL of dry toluene, and 20.0mmol of diarylamine, 30.0mmol of sodium tert-butoxide, and 0.2mmol of Pd were added 2 (dba) 3 And 0.4mmol of XantPhos, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, filtering, washing a filter cake with water and ethanol, drying, and separating and purifying by using a silica gel column to obtain a compound C647;
T 2 : o; white solid, yield: 85%, MS (MALDI-TOF): m/z =828.3272[ m + H ]] + ； 1 HNMR(δ、CDCl 3 )：8.37(1H,s)；8.06(1H,s)；7.97～7.93(1H,m)；7.89～7.82(4H,m)；7.80～7.76(2H,m)；7.55～7.48(6H,m)；7.40～7.27(11H,m)；7.24～7.11(10H,m)；7.06～7.01(2H,m)；6.98～6.93(1H,m)；4.92(1H,s)；4.78(1H,s)。
With reference to the above-described analogous synthetic procedures, the following compounds shown in table 3 were prepared:
TABLE 3
Example 3
An organic electroluminescent device 100, the structure of which is shown in fig. 1, includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer (CPL) 111, and a method for manufacturing the device without the hole blocking layer 107 includes the following steps:
1) And (3) carrying out ultrasonic treatment on the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, washing in deionized water, carrying out ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baking in a clean environment until the glass substrate is completely dried, irradiating for 10 minutes by using an ultraviolet cleaning machine, and bombarding the surface by using low-energy cation beams.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to less than 1 × 10 -5 Pa, depositing silver on the ITO film as anode layer to obtain a deposited film with a thickness of
Evaporating compounds HI01 and HI102 as hole injection layer, wherein HI102 is 3% of HI01 mass, and the thickness of the evaporated film is
3) Continuously depositing a compound HTM on the hole injection layer to form a hole transport layer, wherein the deposition film has a thickness of
4) The compound represented by the formula (I) of the present invention is further deposited on the hole transport layer as an electron blocking layer, and the thickness of the deposited film is
5) Continuously evaporating PHT as main material and GD019 as doping material on the electron blocking layer, wherein GD019 is 3% of PHT mass as organic light emitting layer, and the thickness of the evaporation film is
6) And continuously evaporating a layer of LiQ and ET010 on the organic light-emitting layer to form an electron transport layer, wherein the mass ratio of LiQ to ET010 is 50
7) Continuously evaporating a layer of LiF on the electron transport layer to form an electron injection layer, wherein the thickness of the evaporated film is
8) And evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer, wherein the mass ratio of magnesium to silver is 1
9) Depositing a CPL layer as an element of NPB on the transparent cathode layer to a thickness of
The OLED element provided by the invention is obtained.
The structures of the compounds HI01, HI102, HTM, PHT, GD019, ET010 and LiQ used in example 3 are as follows:
example 4
An organic electroluminescent device 200, as shown in fig. 2, includes a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be fabricated by sequentially depositing the described layers with reference to the fabrication method of example 3.
Comparative example 1
Following the same procedure as in example 3, the compound represented by formula (I) in step 4) was replaced with B-1 to give comparative element 1; b-1 has the following structural formula:
comparative example 2
Following the same procedure as in example 3, the compound represented by formula (I) in step 4) was replaced with B-2 to give comparative element 2; b-2 has the following structural formula:
the driving voltage and current efficiency of the organic electroluminescent element prepared in example 3 and comparative examples 1 and 2 and the lifetime of the element were measured using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m 2 The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the brightness to the current density is the current efficiency; the LT90% lifetime test is as follows: using a luminance meter at 1000cd/m 2 At luminance, the luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current 2 Time in hours. The data listed in table 4 are relative data compared to comparative element 1.
TABLE 4 test results of the performance of each element
As can be seen from Table 4, the light-emitting element prepared by using the fluorene derivative of the present invention as an electron blocking layer material was also at 10mA/cm 2 Under the condition, the driving voltage is reduced compared with B-1 and B-2, the luminous efficiency and LT90% service life performance are obviously improved, and the luminous efficiency can reach 1.4 times of that of a comparison element, so that the compound parent nucleus of the invention has improved stability and is an electron barrier layer material with excellent performance.
Compared with the compound B-1 of a comparative example, the fluorene derivative disclosed by the invention has the difference that B-1 is an orthogonal structure of spirobifluorene and has small plane conjugation, but the fluorene derivative disclosed by the invention contains a homopterapterene structure, has enhanced plane conjugation and plane superposition, has excellent performance in molecular film formation and charge transmission, and has more balanced charge transmission in an element, so that the element performance is improved, and the compound disclosed by the invention has more excellent performance in a light-emitting element.
Compared with the compound B-2 of a comparative example, the fluorene derivative disclosed by the invention is characterized in that B-2 is a rigid structure formed by adamantane and fluorene and is weak in plane conjugation, while the fluorene derivative disclosed by the invention contains conjugated benzene homoptera-pterene, is strong in plane conjugation capability, is excellent in molecular film formation and charge transmission performance, and is more balanced in exciton transmission in an element, so that the element performance is improved, and the compound disclosed by the invention is more excellent in performance of a light-emitting element.
Although the invention has been described in detail with respect to the general description and the specific embodiments thereof, it will be apparent to those skilled in the art that modifications and improvements can be made based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A fluorene derivative containing homotriptycene is characterized in that the structural formula of the fluorene derivative is shown as a formula (I):
wherein the content of the first and second substances,
R 1 ～R 5 each independently selected from hydrogen, deuterium, C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heteroaryl or a group of formula (II);
x, y, z, n and m are independently selected from integers of 0-4;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
w is an integer from 0 to 5;
l is selected from single bond, substituted or unsubstituted C 6 -C 60 Or substituted or unsubstituted C 2 -C 60 Heteroarylene groups.
2. Homotriptycene-containing fluorene derivative of claim 1, wherein R is 1 Is a group shown in formula (II), and x is 1; and/or
R 2 Is a group of formula (II), y is 1; and/or
R 3 Is a group of formula (II), z is 1; and/or
R 4 Is a group shown in formula (II), n is 1; and/or
R 5 Is a group shown in formula (II), m is 1;
R 1 ～R 5 each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, t-butyl, nitrile, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
w is 0, 1 or 2.
3. The homotriptycene-containing fluorene derivative of claim 1, wherein R is 1 ～R 5 At least one of them is a group represented by the formula (II);
R 1 ～R 5 each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, t-butyl, nitrile, substituted or unsubstituted carbazolyl.
4. According to claim 1The fluorene derivative containing homotriptycene is characterized in that Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
l is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted fluorenylene group, and a substituted or unsubstituted carbazolyl group.
5. The homotriptycene-containing fluorene derivative of claim 1, wherein L is selected from a single bond or a group consisting of III-1 to III-16:
wherein the content of the first and second substances,
Z 11 、Z 12 each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C 1 -C 60 Alkyl of (C) 2 -C 60 Alkenyl of, C 2 -C 60 Alkynyl of, C 1 -C 60 Alkoxy group of (1), C 3 -C 60 Cycloalkyl of (C) 3 -C 60 With cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or notSubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylsulfonyl ether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 1 represents O, S, CR ' R ' or NAr ';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 -C 60 Alkyl of (C) 1 -C 60 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 -C 60 Alkyl of (C) 1 -C 60 Heteroalkyl of (a), C 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, ar' is methyl, ethyl, phenyl or naphthyl;
6. The homopteriylene-containing fluorene derivative according to any one of claims 1-5, wherein said homopteriylene-containing fluorene derivative is selected from the group consisting of C602 to C772:
wherein, x-T 2 -is selected from-O-, -S-, or one of the following structures:
* -and-represent a connecting bond.
7. An organic electroluminescent material characterized in that its raw material comprises the homotriptycene-containing fluorene derivative according to any one of claims 1 to 6.
8. An organic electroluminescence element, comprising: a first electrode, a second electrode, a light extraction layer, and one or more organic layers disposed between the first electrode and the second electrode; at least one of the organic layer and the light extraction layer includes the homotriptycene-containing fluorene derivative according to any one of claims 1 to 6.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises at least one of: a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer; the selected one or more layers among the respective layers are formed through a deposition process or a solution process.
10. The organic electroluminescent element according to claim 8 or 9, wherein the organic electroluminescent element is used in any one of the following devices:
a flat panel display device;
a flexible display device;
a monochromatic or white flat panel illumination device; or
A monochromatic or white flexible lighting device.
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| CN116102560A (en) * | 2023-04-07 | 2023-05-12 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
| CN116120328A (en) * | 2023-04-07 | 2023-05-16 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
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| CN114957094A (en) * | 2022-06-09 | 2022-08-30 | 北京八亿时空液晶科技股份有限公司 | Polysubstituted carbazole derivative and application thereof |
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| CN113651858A (en) * | 2021-09-10 | 2021-11-16 | 上海八亿时空先进材料有限公司 | Transition metal complex, organic electroluminescent element and consumer product |
| CN114957094A (en) * | 2022-06-09 | 2022-08-30 | 北京八亿时空液晶科技股份有限公司 | Polysubstituted carbazole derivative and application thereof |
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| CN116102560A (en) * | 2023-04-07 | 2023-05-12 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
| CN116120328A (en) * | 2023-04-07 | 2023-05-16 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
| CN116120328B (en) * | 2023-04-07 | 2023-06-20 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
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