CN113004259A - Compound with anthrone skeleton as core and application thereof - Google Patents
Compound with anthrone skeleton as core and application thereof Download PDFInfo
- Publication number
- CN113004259A CN113004259A CN201911322702.0A CN201911322702A CN113004259A CN 113004259 A CN113004259 A CN 113004259A CN 201911322702 A CN201911322702 A CN 201911322702A CN 113004259 A CN113004259 A CN 113004259A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 230000000903 blocking effect Effects 0.000 claims abstract description 14
- 239000010410 layer Substances 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 239000002346 layers by function Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- -1 biphenylyl Chemical group 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 60
- 230000009477 glass transition Effects 0.000 abstract description 6
- 230000002035 prolonged effect Effects 0.000 abstract description 6
- 239000004065 semiconductor Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001616 biphenylenes Chemical group 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention discloses a compound taking an anthrone skeleton as a core and application thereof, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (1):
the compound provided by the invention has higher triplet state energy level, higher glass transition temperature and molecular thermal stability; when the organic light emitting diode is used as a light emitting layer or a hole blocking layer or an electron transport layer material of an OLED light emitting device, the light emitting efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
Description
Technical Field
The invention relates to a compound taking an anthrone skeleton as a core and application thereof, belonging to the technical field of semiconductors.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has a very wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides an organic compound with an anthrone skeleton as a core and applications thereof. The compound provided by the invention has an anthrone mother nucleus and a carbazole derivative branched chain, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme provided by the invention is as follows: a compound with an anthrone skeleton as a core has a structure shown in a general formula (1):
in the general formula (1), m, n, i and j respectively represent 0 or 1, and m + n + i + j is more than or equal to 1;
x represents a carbon atom, an oxygen atom or a sulfur atom;
when X represents a carbon atom, k is 1;
when X represents an oxygen atom or a sulfur atom, k ═ m ═ n ═ 0;
Ar1-Ar4each independently represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms; ar (Ar)3And Ar4Can be connected with each other to form a ring;
z represents a nitrogen atom or C (R), Z being the same or different on each occurrence;
A. b, C, D each independently represents a hydrogen atom, a structure represented by general formula (2), general formula (3), or general formula (4): and are not simultaneously represented as hydrogen atoms;
in the general formula (2), Z1Represented by nitrogen atom or C (R)2)，Z1Each occurrence is the same or different;
ar represents substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms; and when Z is1When all are represented by CH, Ar is represented by C6-C30One of an aryl group, a 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (3), Z2Represented by nitrogen atom or C (R)3)，Z2Each occurrence is the same or different;
in the general formula (4), Z3Represented by nitrogen atom or C (R)4)，Z3Each occurrence is the same or different;
R、R2、R3、R4represented by hydrogen atom, halogen, cyano, C1-C10Alkyl of (C)1-C10Alkoxy, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (3), when Z is2All are represented by C (R)3) When at least one R is present3Represents a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (4), R1Is represented by substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, and R1Is connected with the general formula (4) in a ring-merging mode;
the substituent of the substitutable group is selected from cyano, halogen and C1-C20Alkyl radical, C2-C20Alkenyl radical, C6-C30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, R is1Represented by any of the following structures (5) or (6):
X1、X2each independently represents a single bond, -O-, -S-, -CR5R6-or N-R7And X1、X2Not simultaneously represent a single bond;
R5、R6、R7each independently represents substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-C30Aryl, heteroaryl, and heteroaryl,Substituted or unsubstituted C2-C30A heteroaryl group;
structure (5), structure (6) and structure (7) are connected in parallel to the adjacent sites marked by "+" of general formula (4).
As a further improvement of the invention, Ar is1、Ar2、Ar3、Ar4Each independently represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted furylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted diphenylfluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group;
ar represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted azacarbazolyl;
the R, R2、R3、R4Represented by a hydrogen atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group;
the R is1Represented by substituted or unsubstituted phenyl, substituted or unsubstitutedSubstituted or unsubstituted indolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl;
the substituent of the substitutable group is one or more selected from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuryl, carbazolyl or pyridyl.
As a further improvement of the present invention, the compound structure is represented by any one of general formula (II-1) to general formula (II-27):
as a further improvement of the present invention, the specific structure of the compound is:
An organic electroluminescent device comprises a cathode, an anode and an organic functional layer, wherein the organic functional layer is positioned between the cathode and the anode, and at least one organic functional layer in the organic electroluminescent device contains the compound taking an anthrone skeleton as a core.
In a further improvement of the present invention, the organic functional layer includes a light-emitting layer containing the compound having an anthrone skeleton as a core.
In a further improvement of the present invention, the organic functional layer includes a hole blocking layer containing the compound having the anthrone skeleton as a core.
As a further improvement of the invention, the organic functional layer comprises an electron transport layer, and the electron transport layer contains the compound taking the anthrone skeleton as the core.
A lighting or display element comprising the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound of the invention takes the anthrone skeleton as a mother nucleus and is connected with the branched chain of the carbazole derivative, and the structure has stronger rigidity, large steric hindrance and difficult rotation, so that the three-dimensional structure of the compound material of the invention is more stable. The appropriate LUMO energy level of the compound can effectively realize electron transmission, improve the recombination efficiency of excitons in a light-emitting layer, reduce energy loss, and fully transfer the energy of a main material of the light-emitting layer to a doping material, thereby improving the light-emitting efficiency of the material after the material is applied to a device.
(2) When the compound is used as a main material of a light-emitting layer, the distribution of electrons and holes in the light-emitting layer is more balanced, and the hole injection and transmission performance is improved under the proper HOMO energy level; when the carbazole derivative is used as a luminescent functional layer material of an OLED luminescent device, an anthrone skeleton is taken as a mother nucleus and matched with the carbazole branched chain in the range of the invention, so that the utilization rate of excitons and the high fluorescence radiation efficiency can be effectively improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.
(3) The compound is designed on an anthrone skeleton group, a carbazole derivative substituent group is added, and the material has high Tg temperature and good stability; the intermolecular force is small, so that the compound provided by the invention has a small evaporation temperature, the evaporation material is not decomposed for a long time in mass production, the influence of heat radiation of the evaporation temperature on the deformation of the Mask is reduced, and the use and processing window of the material is improved.
(4) The pi conjugation effect in the compound has strong electron transmission capacity, and the high electron transmission rate can reduce the initial voltage of the device and improve the efficiency of the organic electroluminescent device;
(5) the compound provided by the invention has deep HOMO and LUMO energy levels and high electron mobility, and the HOMO and LUMO energy levels can be freely adjusted through modification of other substituent groups; the higher T1 energy level ensures the energy transfer efficiency between the host and the guest, and can inhibit the energy loss in the luminescent layer when being used as a hole barrier layer material, thereby not only being used as an electronic luminescent host material, but also being used as a hole barrier layer material and an electronic transmission layer material;
(6) the carbazole derivative substituent group connected to the anthrone skeleton of the compound enables the distance between molecules to be increased, and the interaction force between cores between molecules to be weakened, so that the compound has lower evaporation temperature, and the industrial processing window of the material is widened;
(7) the compound has the characteristics of strong group rigidity, difficult intermolecular crystallization and aggregation, good film forming property and high glass transition temperature and thermal stability, so when the compound is applied to an OLED device, the stability of a film layer formed by the material can be kept, and the service life of the OLED device is prolonged. After the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
All reactants in the following examples were purchased from cigarette Taiwangrun Fine chemical Co., Ltd.
Preparation of reactant B-1
(1) Adding 0.01mol of raw material X-1, 0.012mol of raw material X-2 and 150mL of toluene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, then adding 0.03mol of sodium tert-butoxide and 5 multiplied by 10-5molPd2(dba)3，5×10-5Heating the mol of tri-tert-butylphosphine to 105 ℃, and carrying out reflux reaction for 24 hours until the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain an intermediate Y-1;
(2) adding 0.02mol of intermediate Y-1 and 40mL of tetrahydrofuran in a 250mL three-neck flask in the atmosphere of introducing nitrogen to completely dissolve, cooling to-78 ℃, then adding 15mL of 1.6mol/L tetrahydrofuran solution of n-butyllithium into a reaction system, reacting for 3 hours at-78 ℃, adding 0.024mol of triisopropyl borate, reacting for 2 hours, then raising the temperature of the reaction system to 0 ℃, adding 50mL of 2mol/L hydrochloric acid solution, stirring for 3 hours, completely reacting, adding diethyl ether for extraction, adding anhydrous magnesium sulfate into an extract, drying, carrying out rotary evaporation, and recrystallizing by using an ethanol solvent to obtain an intermediate Y-2;
(3) a250 mL three-necked flask was charged with 0.01mol of intermediate Y-2 and 0.015mol of raw material X-3 in a nitrogen-purged atmosphere, dissolved in a mixed solvent (90mL of toluene and 45mL of ethanol), and then charged with 0.03mol of Na2CO3The aqueous solution (2M) was stirred under nitrogen for 1 hour, then 0.0001mol of Pd (PPh) was added3)4And heating and refluxing for 15 hours, sampling a sample point plate, and completely reacting. Naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate Y-3;
(4) adding 0.02mol of intermediate Y-3 and 40mL of tetrahydrofuran in a 250mL three-neck flask in the atmosphere of nitrogen gas for completely dissolving, cooling to-78 ℃, then adding 15mL of 1.6mol/L tetrahydrofuran solution of n-butyllithium into a reaction system, reacting for 3h at-78 ℃, then adding 0.024mol of triisopropyl borate for reacting for 2h, then raising the temperature of the reaction system to 0 ℃, adding 50mL of 2mol/L hydrochloric acid solution, stirring for 3h, completely reacting, adding diethyl ether for extraction, adding anhydrous magnesium sulfate into an extract for drying, carrying out rotary evaporation, and recrystallizing by using an ethanol solvent to obtain a reactant B-1, wherein the yield is 74.39%, and the HPLC purity is 98.69%.
Elemental analysis Structure (molecular formula C)48H32BN3O2): theoretical value: c, 83.12; h, 4.65; b, 1.56; n, 6.06; test values are: c, 83.10; h, 4.67; b, 1.58; and N, 6.03. LC-MS: theoretical value is 693.26, found 693.21.
Preparation of reactant B-6
(1) Adding 0.01mol of raw material X-4, 0.012mol of raw material X-2 and 150mL of toluene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, then adding 0.03mol of sodium tert-butoxide and 5 multiplied by 10-5molPd2(dba)3，5×10-5Heating the mol of tri-tert-butylphosphine to 105 ℃, and carrying out reflux reaction for 24 hours until the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain an intermediate Y-4;
(2) a250 mL three-necked flask was charged with 0.01mol of intermediate Y-4 and 0.015mol of raw material X-5 in a nitrogen-purged atmosphere, dissolved in a mixed solvent (90mL of toluene and 45mL of ethanol), and then charged with 0.03mol of Na2CO3The aqueous solution (2M) was stirred under nitrogen for 1 hour, then 0.0001mol of Pd (PPh) was added3)4And heating and refluxing for 15 hours, sampling a sample point plate, and completely reacting. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a reactant B-6, wherein the yield is 79.31 percent, and the HPLC purity is 99.08 percent.
Elemental analysis Structure (molecular formula C)36H23BN2O2): theoretical value: c, 82.14; h, 4.40; b, 2.05; n, 5.32; test values are: c, 82.13; h, 4.41; b, 2.08; n, 5.34. LC-MS: theoretical value is 526.19, found 526.24.
EXAMPLE 1 preparation of Compound 2
A250 mL three-necked flask was charged with 0.01mol of the reactant A-1 and 0.015mol of the reactant B-1 in a nitrogen-purged atmosphere, dissolved in a mixed solvent (90mL of toluene and 45mL of ethanol), and then charged with 0.03mol of Na2CO3The aqueous solution (2M) was stirred under nitrogen for 1 hour, then 0.0001mol of Pd (PPh) was added3)4And heating and refluxing for 15 hours, sampling a sample point plate, and completely reacting. Naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain a compound 2; the yield was 76.06%, HPLC purity 98.72%.
Elemental analysis Structure (molecular formula C)61H37N3O2): theoretical value: c, 86.81; h, 4.42; n, 4.98; test values are: c, 86.82; h, 4.40; and N, 4.99. LC-MS: theoretical value is 843.29, found 843.22.
The procedure of example 1 was repeated to synthesize the following compounds, except that the reactants A and B listed in the following Table 1-1 were used.
TABLE 1-1
For structural analysis of the compounds prepared in examples 1 to 24, the molecular weight was measured using LC-MS, and 1H-NMR was measured by dissolving the prepared compound in a deuterated chloroform solvent and using an NMR apparatus of 500 MHz.
Nuclear magnetic data as follows
Tables 1 to 2
The compound of the invention is used in a light-emitting device and can be used as a material of a light-emitting layer, a hole blocking layer or an electron transport layer. The compounds prepared in the above examples of the present invention were respectively tested for HOMO, LUMO level, triplet level (T1) and glass transition temperature (Tg), and the results are shown in table 2:
TABLE 2
Note: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg was measured by a two-beam uv-vis spectrophotometer (model: TU-1901), LUMO ═ HOMO + Eg.
The data in the table show that the organic compound has high glass transition temperature, can be applied to improving the phase stability of material films and further prolonging the service life of devices; the organic compound of the present invention has appropriate HOMO and LUMO energy levels, so that the problem of carrier injection can be solved, and the device voltage can be reduced. The organic compound has a high T1 energy level, can ensure the energy transfer efficiency between a host and an object when used as a host material, and can effectively inhibit energy loss when used as a hole blocking layer. Therefore, after the organic material is applied to different functional layers of an OLED device, the voltage of the device can be effectively reduced, and the service life of the device can be prolonged.
The effect of the use of the compounds of the present invention in OLED devices will now be illustrated by device examples 1-24 and device comparative examples 1-7. Device examples 2 to 24 and device comparative examples 1 to 7 were completely the same as device example 1 in terms of manufacturing processes, and the same substrate material and electrode material were used, and the film thicknesses of the electrode materials were also kept the same, except that the materials of the light-emitting layer, the hole-blocking layer, or the electron-transporting layer in the devices were changed, the composition of each layer of each device is shown in table 3, and the performance test results of each device are shown in table 4.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with a detergent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were deposited by a vacuum deposition apparatus as the hole injection layer 3, and the film thickness was 10nm, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated as a hole transport layer 4 to a thickness of 130 nm. EB-1 was subsequently evaporated as an electron blocking layer 5 with a thickness of 40 nm. After the evaporation of the electron blocking layer material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that a compound 2 and GH-2 used by the OLED light emitting layer 6 are used as main body materials, GD-1 is used as a doping material, the doping proportion of the doping material is 6% (mass ratio), and the thickness of the light emitting layer is 40 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 35nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a Yb layer having a film thickness of 1nm was formed by a vacuum deposition apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9. On the cathode layer 10, CP-1 was vacuum-deposited as the CPL layer 11, and the thickness was 70 nm. The organic electroluminescent device 1 is obtained.
The composition of each layer of each device is shown in table 3, the performance test result of each device is shown in table 4, and the structural formula of the material used by each device is as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the voltage, current efficiency, light emission spectrum, and lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 3; the results of the tests of voltage, current efficiency, color and LT95 lifetime at 10000nits luminance of the resulting device are shown in table 4.
TABLE 3
TABLE 4
Note: voltage, current efficiency and color coordinates were tested at a current density of 10mA/cm2 using an IVL (current-voltage-brightness) test system (frastd scientific instruments, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95% at 10000 nits.
As can be seen from the device data results in table 4, the organic light emitting device of the present invention has a greater improvement in device efficiency and device lifetime compared to the OLED devices of known materials, as compared to comparative devices 1-7. At the same time, the voltage of the organic light emitting device of the present invention is reduced compared to OLED devices of known materials.
Claims (10)
1. A compound having an anthrone skeleton as a core, characterized in that the structure of the compound is represented by the general formula (1):
in the general formula (1), m, n, i and j respectively represent 0 or 1, and m + n + i + j is more than or equal to 1;
x represents a carbon atom, an oxygen atom or a sulfur atom;
when X represents a carbon atom, k is 1;
when X represents an oxygen atom or a sulfur atom, k ═ m ═ n ═ 0;
Ar1-Ar4each independently represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms; ar (Ar)3And Ar4Can be connected with each other to form a ring;
z represents a nitrogen atom or C (R), Z being the same or different on each occurrence;
A. b, C, D each independently represents a hydrogen atom, a structure represented by general formula (2), general formula (3), or general formula (4): and are not simultaneously represented as hydrogen atoms;
in the general formula (2), Z1Represented by nitrogen atom or C (R)2)，Z1Each occurrence is the same or different;
ar represents substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms; when Z is1When all are represented by CH, Ar is represented by C6-C30One of an aryl group, a 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (3), Z2Represented by nitrogen atom or C (R)3)，Z2Each occurrence is the same or different;
in the general formula (4), Z3Represented by nitrogen atom or C (R)4)，Z3Each occurrence is the same or different;
R、R2、R3、R4represented by hydrogen atom, halogen, cyano, C1-C10Alkyl of (C)1-C10Alkoxy, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (3), when Z is2All are represented by C (R)3) When at least one R is present3Represents a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
in the general formula (4), R1Is represented by substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, and R1Is connected with the general formula (4) in a ring-merging mode;
the substituent of the substitutable group is selected from cyano, halogen and C1-C20Alkyl radical, C2-C20Alkenyl radical, C6-C30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
2. The compound of claim 1, wherein R is an anthrone skeleton-based compound1Represented by any of the following structures (5) or (6):
X1、X2each independently represents a single bond, -O-, -S-, -CR5R6-or N-R7And X1、X2Not simultaneously represent a single bond;
R5、R6、R7each independently represents substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30A heteroaryl group;
structure (5), structure (6) and structure (7) are connected in parallel to the adjacent sites marked by "+" of general formula (4).
3. The compound of claim 1, wherein Ar is selected from the group consisting of1、Ar2、Ar3、Ar4Each independently represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted furylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted diphenylfluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group;
ar represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted azacarbazolyl;
the R, R2、R3、R4Represented by a hydrogen atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group;
the R is1Represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group;
the substituent of the substitutable group is one or more selected from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuryl, carbazolyl or pyridyl.
4. The compound of claim 1, wherein the structure of the compound is represented by any one of general formula (ii-1) to general formula (ii-27):
5. the compound with the anthrone skeleton as the core according to claim 1, wherein the specific structure of the compound is as follows:
6. An organic electroluminescent device comprising a cathode, an anode and an organic functional layer, wherein the organic functional layer is located between the cathode and the anode, characterized in that at least one organic functional layer in the organic electroluminescent device comprises the compound having an anthrone skeleton as a core according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises a light-emitting layer, and the light-emitting layer contains the compound having an anthrone skeleton as a core according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises a hole blocking layer, and the hole blocking layer contains the compound having an anthrone skeleton as a core according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises an electron transport layer, and the electron transport layer contains the compound having an anthrone skeleton as a core according to any one of claims 1 to 5.
10. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6 to 9.
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