CN116715677A - Compound, organic electroluminescent material containing same, organic electroluminescent device and consumer product - Google Patents
Compound, organic electroluminescent material containing same, organic electroluminescent device and consumer product Download PDFInfo
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- CN116715677A CN116715677A CN202310570514.XA CN202310570514A CN116715677A CN 116715677 A CN116715677 A CN 116715677A CN 202310570514 A CN202310570514 A CN 202310570514A CN 116715677 A CN116715677 A CN 116715677A
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000003981 vehicle Substances 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
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Abstract
The invention relates to the technical field of organic electroluminescence, in particular to a compound, an organic electroluminescent material containing the compound, an organic electroluminescent device and a consumer product, wherein the structural general formula of the compound is shown as formula (I):in the compound shown in the general formula (I), the compound contains an oxazole group with strong electronicity and at least one triarylamine group or heteroaryl group which are mutually crossed in the space structure, so that the free rotation of the groups is avoided, the material has higher density and higher refractive index is obtained; meanwhile, the material has higher glass transition temperature, and the vapor deposition temperature of the material under vacuum is generally lower than 350 ℃, so that the material is not decomposed during vapor deposition for a long time, and the deformation influence of heat radiation at the vapor deposition temperature on a vapor deposition mask is reduced, and the material is suitable for being used as a constituent material of the organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound, an organic electroluminescent material containing the compound, an organic electroluminescent device and a consumer product.
Background
Organic Light Emitting Diodes (OLEDs), also known as organic electroluminescent devices, are a technology in which an organic material emits light by carrier injection and recombination under the action of an electric field, and it is capable of converting electric energy into light energy through the organic light emitting material, including passive-driven OLEDs (PMOLEDs) and active-driven OLEDs (AMOLEDs). OLEDs are a new generation of display technology following Cathode Ray Tubes (CRTs), liquid Crystal Displays (LCDs), known as fantasy display technology. OLEDs also show good development prospects in communication terminals, military fields and flexible displays. However, the development time of OLED is still short compared with other display technologies, so that the theoretical system related to the organic electroluminescent display technology is still not fully systematic, and the field is also full of opportunities and challenges, such as poor device efficiency, higher manufacturing requirements and cost, short device lifetime, poor stability, and the like, which still remain to be solved.
One of the key factors affecting the efficiency of an OLED device is the injection and recombination process of carriers in the device, and research shows that the efficiency of the device can be effectively improved by balancing the carriers. However, the balance of carriers is difficult to control, which affects exciton recombination luminescence of the light-emitting layer, resulting in lower device efficiency. At present, the hole transmission rate in an OLED device is far higher than the electron transmission rate, so that the development of an electron transmission material with high transmission rate is an effective way for improving the luminous efficiency of the device, and has important research significance. Some common electron transport materials, such as metal organic complexes, have good film forming property and excellent electron transport property; the quinoline material has low reduction potential value, good mechanical property and high thermal stability; the triazine compound has the advantages of excellent heat resistance, higher electron affinity potential energy and the like; the oxadiazole molecules have the advantages of excellent chemical stability, high electron transmission rate, capability of reducing starting voltage, good thermal stability and the like.
The structure of the oxazole is similar to that of the oxadiazole, and the oxazole has electron-deficient performance, but hole materials and luminescent layer materials containing the oxazole are unusual, and the structure of the oxazole is not paid attention to in the aspect of photoelectric materials. Before the present, the research finds that the performance of the material serving as a hole material and a luminescent layer material can be researched by carrying out functional modification on the material, so that the blind area of the research of the oxazole serving as a functional material is filled, and a foundation is laid for future scientific research work.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
The invention provides a compound, an organic electroluminescent material, an organic electroluminescent device and a consumer product containing the compound, and aims to solve the technical problems in the prior art.
The first object of the present invention is to provide a compound.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a compound has a structural general formula shown in a formula (I):
wherein X is 1 Selected from O, S, CR 9 R 10 Or NR (NR) 11 ；
R 1 、R 11 Each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 5 ～C 50 Arylsilyl groups;
R 2 ～R 10 Each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Aryl silyl group, any adjacent two or more R 2 ～R 10 Optionally joined or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
and at R 2 ～R 8 At least one of which is a group of formula (II);
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine groups;
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
* -a linking site representing a group.
Further, the compound is selected from the group consisting of the following structures:
wherein R is 1 ～R 7 、X 1 、L 1 、m、Ar 1 And Ar is a group 2 The meaning of (2) is the same as defined above.
Preferably, m is selected from 0, 1 or 2.
Ar 3 、Ar 4 Each independently selected from substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine groups.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like;
aryl groups in the sense of the present invention contain 6 to 60 carbon atoms, heteroaryl groups contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the hetero atoms are preferably selected from N, O orS, S. In this case, two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, or may further include a condensed form with the aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular groups selected from the following: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, id ]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxaoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, erythrozinyl, naphthyridinyl, 1,2, 3-triazolyl, 1, 2-triazolyl, 1, 3-triazolyl, 1, 4-naphthyridinyl A group of triazolyl, 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, indolizinyl, quinazolinyl, benzothiadiazolyl, or a group derived from a combination of these systems.
"halogen" or "halogen atom" as used herein means a member selected from fluorine, chlorine, bromine or iodine.
Further, the R 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylA group selected from the group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, and formula (II).
Further, the R 2 ～R 8 Each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen atoms, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthracenylSubstituted or unsubstituted pyrenyl, substituted or unsubstitutedA group selected from the group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, and wherein R is 2 ～R 8 At least one of which is a group of formula (II).
Further, the R 9 、R 10 Each independently selected from the group consisting of hydrogen, methyl, ethyl, phenyl, fluorenyl.
Further, the Ar 1 、Ar 2 、R 11 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenylA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophene group.
Heteroalkyl in the sense of the present invention means a hydrogen atom or-CH on an alkyl radical 2 Substituted by at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples, difluoromethylTrifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, and the like. Haloalkyl refers to the partial substitution or total substitution of a hydrogen atom on an alkyl group with a halogen, and as non-limiting examples there are fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl and the like.
Alkenyl or alkynyl groups useful in the present invention contain at least two carbon atoms, and are preferably considered to mean, by way of non-limiting example, the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.
Alkoxy, alkylthio, preferably alkoxy or alkylthio having 1 to 40 carbon atoms, as used in the present invention is understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The radicals can be replaced by N, O or STo form heterocycloalkyl, heterocycloalkenyl, e.g. one-CH in cyclopentyl 2 -the radical is replaced by O to form one of the groups-CH in the tetrahydrofuranyl, cyclohexyl 2 -the group is replaced by O to form tetrahydropyranyl, etc.; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Aryloxy as used herein refers to R' O - The monovalent functional group represented by R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
As used herein, arylthio means a monovalent functional group represented by R 'S-wherein R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such arylthio groups, phenylthio, naphthylthio, biphenylthio and the like are mentioned.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Aryl silicon group refers to alkyl silicon group substituted with at least one aryl group having 6 to 60 carbon atoms, and examples of the alkyl silicon group include phenyl dimethyl silicon group, naphthyl dimethyl silicon group, phenyl diethyl silicon group, diphenyl methyl silicon group, diphenyl ethyl silicon group, triphenyl silicon group, and the like.
"alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylborocarbonyl", "alkylborocarbonyl" in the sense of the present invention means a substituted carbonyl (-COR) wherein R is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboronyl, alkylboronyl.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylphosphorus group, there are diphenylphosphorus group, bis (4-trimethylsilylbenzene) phosphorus group and the like. The phosphorus atom of the aryl phosphorus oxide group is the diaryl phosphorus group is oxidized to the highest valence state.
The arylboron group used in the present invention means a diarylboroyl group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylboron group, there are diphenyl boron group, bis (2, 4, 6-trimethylbenzene) boron group and the like. The alkylboryl group means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
The arylalkyl group according to the present invention means an alkyl group in which at least one hydrogen atom of a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms is substituted with an aryl group having from 6 to 60 carbon atoms, and as a non-limiting example, phenylmethyl group, diphenylmethyl group, triphenylmethyl group, 2-phenylethyl group, 3-phenylpropyl group and the like can be mentioned.
Alkylaryl according to the present invention refers to an aryl group in which at least one hydrogen atom of the aryl group having from 6 to 60 carbon atoms is substituted with a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms, and as a non-limiting example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl and the like can be mentioned.
Preferably, the heteroaryl is selected from the group consisting of groups II-1 to II-13:
wherein,,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, substituted or unsubstituted C 6 -C 60 Arylamino groups, or substituted or unsubstitutedSubstituted C 2 -C 60 Heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 representation O, S or NAr ’ ；
Ar ’ Selected from C 1 ～C 40 Alkyl, C of (2) 1 ～C 40 Heteroalkyl 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 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups; preferably Ar ’ Methyl, ethyl, phenyl, biphenyl or naphthyl;
representing the attachment site of the group.
Further, the heteroaryl is selected from the group consisting of groups of formulas II-1 to II-13.
The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted condensed aryl, substituted arylene, substituted heteroarylene described herein are each independently selected from at least one of the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C 1 -C 40 Alkyl, C 1 -C 40 Haloalkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 1 -C 40 Alkylthio, C 3 -C 40 Cycloalkyl, C 3 -C 40 Cycloalkenyl, 3-to 7-membered heterocycloalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, unsubstituted or substituted by one or more C 6 -C 60 Aryl-substituted 3-to 30-membered heteroaryl, unsubstituted or deuterated, one or more C 1 -C 40 C substituted with at least one of an alkyl group and one or more 3-to 30-membered heteroaryl groups 6 -C 60 Aryl, tris (C) 1 -C 40 ) Alkylsilyl, tri (C) 6 -C 60 ) Aryl silicon based, di (C) 1 -C 40 ) Alkyl (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkyldi (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkylcarbonyl, C 1 -C 40 Alkoxycarbonyl group, C 6 -C 60 Arylcarbonyl, di (C) 6 -C 60 ) Arylborocarbonyl groups of di (C) 1 -C 40 ) Alkyl boron carbonyl, C 1 -C 40 Alkyl (C) 6 -C 60 ) Arylborocarbonyl, C 6 -C 60 Aryl (C) 1 -C 40 ) Alkyl, C 1 -C 40 Of alkyl (C) 6 -C 60 ) Aryl groups.
Arylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 60 carbon atoms. As non-limiting examples thereof, there are phenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene and the like.
The heteroarylene or heteroarylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from a heteroarene having 2 to 60 carbon atoms; further, the heteroarylene or heteroarylene of the present invention is selected from divalent functional groups obtained by removing two hydrogen atoms from the group represented by the formula II-1 to II-13, and examples thereof include a pyridylene group, a quinolinylene group, an isoquinolylene group, a carboline group, a pyrimidine group, a triazine group, and the like.
The arylene, heteroarylene groups as described above are linked to N as divalent functional groups, preferably L 1 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
Wherein X is selected from O, S, se, CR ’ R”、SiR ’ R' or NAr ’ ；
Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
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; y5 represents an integer of 1 or 2;
R ’ r' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl 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 formed; preferably, R ’ R' is methyl, phenyl or fluorenyl;
Ar ’ selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, substitutionOr unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably Ar ’ Methyl, ethyl, phenyl, biphenyl or naphthyl;
wherein the dotted line represents the attachment site of the group.
Preferably, X is selected from O or S.
Preferably, the L 1 Each independently selected from a single bond or a group consisting of groups III-1 to III-15, III-25;
preferably, said Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile groups.
Further, the compound is selected from one or more of the following C01-C204 structures:
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wherein X is selected from O, S, CR 9 R 10 Or NR (NR) 11 ；
The R is 9 And R is 10 Methyl, phenyl or fluorenyl, respectively;
the R is 11 Selected from the group consisting of:
as used herein, "combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, the alkyl and deuterium atoms can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
The second object of the invention is to provide an organic electroluminescent material comprising the above-mentioned compound.
The organic electroluminescent material may be constituted by using the compound of the present invention alone or may contain other compounds at the same time.
The compound of the present invention contained in the organic electroluminescent material of the present invention can be used as, but not limited to, a light-emitting layer material, a carrier transporting layer material, a capping layer, or a charge generating layer material.
The third object of the present invention is to provide an organic electroluminescent device comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, the organic layer or capping layer comprising the compound provided by the present invention.
The organic electroluminescent device comprises a cathode, an anode 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-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent device described herein may comprise one light emitting layer, or it may comprise a plurality of light emitting layers. I.e. a plurality of luminescent compounds capable of emitting light are used in the luminescent layer. A system with three light emitting layers is preferred, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent device according to the present 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 anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent device according to the invention, in particular in the hole transport layer and the light-emitting layer, all materials can be used in the manner generally 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 luminescent layer according to the invention without inventive effort.
Furthermore, organic electroluminescent devices are preferred, which apply one or more layers by means of sublimation methods, wherein the sublimation is performed in a vacuum at less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Preference is likewise given to organic electroluminescent arrangements which apply one or more layers by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent devices are preferred in which one or more layers are produced from a solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of novel compounds of formula I. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent device according to the invention, which applies at least one layer by means of a sublimation method and/or at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer from a solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferences as indicated above in relation to the organic electroluminescent device apply to the compounds of the invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires preparations of the compounds according to the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, 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 methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol, triethylene glycol, 1, 2-dimethyl benzene ether, 1-dimethyl-n-butyl ether, 1-dimethyl-butyl benzene, 1-dimethyl-n-butyl benzene, 1-dimethyl-butyl benzene, n-butyl benzene, dimethyl benzene, n-butyl benzene, dimethyl benzene, or a mixture of these solvents.
Further, the organic layer is selected from one or more of an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a charge generation layer.
Further, the hole injection layer, hole transport layer, light emitting layer, capping layer, or charge generation layer comprises the compound of the present invention.
Still further, the hole transport layer, capping layer, or light emitting layer comprises a compound of the present invention.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Compared with the prior art, the invention has the beneficial effects that:
the compound has a naphtho-oxazole rigid structure, so that the structural stability of the material is improved; in the compound represented by the general formula (I), the compound contains an oxazole group with strong electronicity and at least one mutually crossed triarylamine group or heteroaryl group in a space structure, so that the free rotation of the groups is avoided, the material has higher density and higher refractive index is obtained; meanwhile, the material has higher glass transition temperature, and the vapor deposition temperature of the material under vacuum is generally lower than 350 ℃, so that the material is not decomposed during vapor deposition for a long time, and the deformation influence of heat radiation at the vapor deposition temperature on a vapor deposition mask is reduced, so that the material is suitable for being used as a constituent material of the organic electroluminescent element.
When the material is applied to CPL, electron and hole transmission of the element are not involved, but the material has very high requirements on thermal stability, film crystallinity and light transmission, and as analyzed above, the novel compound contains naphtho-oxazole rigid groups, so that the stability and glass transition temperature of the material are improved, and the material is ensured not to be crystallized in a film state; the low evaporation temperature is a precondition that the material can be applied to mass production; the high refractive index is the most important factor in the applicability of the material of the present invention to CPL.
In the case of applying the compound represented by the above general formula (I) of the present invention to the organic electroluminescent element of the present invention, the high electron mobility due to the deep HOMO level can effectively improve the recombination efficiency of holes and electrons in the light emitting layer, thereby improving the light emitting efficiency and the service life of the element.
Further, in the present invention, the light extraction efficiency of the organic electroluminescent element can be maximized after the CPL layer is formed using the compound of the general formula (I).
In the present invention, the organic electroluminescent element of the present invention, in which the compound represented by the general formula (I) is used as a constituent material for at least one of the light-emitting layers or the laminated film in which two or more light-emitting layers are arranged, uses a compound having high carrier mobility, high internal quantum efficiency, excellent amorphism, and stable thin film state, and thus can realize an organic electroluminescent element having high efficiency, low driving voltage, and long lifetime.
Drawings
In order to more clearly illustrate the invention or the technical solutions of the prior art, the following description will briefly explain the drawings used in the embodiments or the description of the prior art, and it is obvious that the drawings in the following description are some embodiments of the invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to a first embodiment of the present invention;
fig. 2 is a schematic structural view of an organic electroluminescent device according to a second embodiment of the present invention;
fig. 3 is a schematic structural view of an organic electroluminescent device according to a third embodiment of the present invention.
Reference numerals:
100, 200: an organic electroluminescent device; 101: a substrate; 102: an anode layer; 103: a hole injection layer; 104: a hole transport layer; 105: an electron blocking layer; 106: a light emitting layer; 1061: a first light emitting layer; 1062: a second light emitting layer; 107: a hole blocking layer; 108: an electron transport layer; 109: an electron injection layer; 110: a cathode layer; 111: a capping layer; 112: a charge generation layer.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings, and it is apparent that the described embodiments are some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid derivatives, can be synthesised by skilled operating skills and are not described in detail in the present invention.
Any range recited in the invention includes any numerical value between the endpoints and any sub-range of any numerical value between the endpoints or any numerical value between the endpoints.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: using an LTS-1004AC life test device;
external quantum efficiency: labsphere LED integrating sphere test system was used.
Example 1
A process for the preparation of compound C02, exemplified by x=o, comprising the steps of:
the first step: preparation of Compound Int-1
Under the protection of nitrogen, 20.0mmol of 2-fluoro-6-iodobenzonitrile is dissolved in 80mL of dry THF, the temperature is reduced to minus 10 ℃, 22.0mmol of o-methoxy phenyl lithium THF solution is added dropwise, stirring reaction is carried out for 2 hours, 100mL of 1M dilute hydrochloric acid aqueous solution is added, extraction is carried out by ethyl acetate, organic phase is collected, drying, filtration and decompression concentration of filtrate are carried out, and separation and purification are carried out by silica gel column to obtain compound Int-1, yellow solid, yield: 87%.
And a second step of: preparation of Compound Int-2
Under the protection of nitrogen, 20.0mmol of Int-1 and 22.0mmol of benzamidopropionine are mixed with 60mL of acetonitrile and 6mL of triethylamine, and 1.0mmol of cuprous iodide and 1.0mmol of PdCl are added 2 (PPh 3 ) 2 The catalyst was heated to reflux and stirred for 2 hours, cooled to room temperature, 100mL of saturated aqueous ammonium chloride solution was added, and ethyl acetate was usedExtracting, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying by a silica gel column to obtain a compound Int-2 as a yellow solid, wherein the yield is as follows: 71%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, mixing 20.0mmol of Int-2 prepared in the previous step, 2.0mmol of silver trifluoroacetate, 50mL of 1, 2-dichloroethane and 20.0mmol of water, stirring at room temperature for reaction for 2 hours, adding 40.0mmol of p-toluenesulfonic acid, heating to 85 ℃ for stirring reaction for 1 hour, cooling to room temperature, adding 50mL of saturated sodium bicarbonate aqueous solution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain a compound Int-3, yellow solid, and obtaining the following yield: 56%.
Fourth step: preparation of Compound Int-4
Under the protection of nitrogen, 20.0mmol of Int-3 prepared in the previous step is dissolved in 60mL of dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron tribromide solution in 10mL of dichloromethane is added dropwise, the reaction is stirred for 1 hour, the temperature is raised to room temperature, 50mL of ice water is added, the dichloromethane is used for extraction, an organic phase is collected, dried, filtered, the filtrate is concentrated under reduced pressure to dryness, and the compound Int-4 is obtained by separation and purification by a silica gel column, yellow solid is obtained in yield: 93%.
Fifth step: preparation of Compound A1
Under the protection of nitrogen, 20.0mmol of Int-4 prepared in the previous step is dissolved in 50mL of DMF, 60.0mmol of anhydrous potassium carbonate is added, the temperature is raised to 125 ℃, the stirring reaction is carried out for 10 hours, the temperature is reduced to room temperature, the reaction solution is poured into 150mL of ice water, dichloromethane is used for extraction, an organic phase is collected, washed with water, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound A1 is obtained by separation and purification by a silica gel column, yellow solid is obtained, and the yield is: 90%.
Sixth step: preparation of Compound Int-5
Under the protection of nitrogen, 20.0mmol of A1 prepared in the previous step is dissolved in 50mL of dichloromethane, the temperature is reduced to 0 ℃, 22.0mmol of N-bromosuccinimide is added in batches, stirring is carried out for 2 hours, 50mL of saturated sodium bisulphite aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected and washed by water, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-5 is obtained by separating and purifying by a silica gel column, yellow solid is obtained, and the yield is: 87%.
Seventh step: preparation of Compound C02
22.0mmol of Int-5 (reactant 1) prepared in the previous step, 20.0mmol of sub-1 (reactant 2), 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd under the protection of nitrogen 2 (dba) 3 Mixing with 80mL of toluene, adding 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 100deg.C, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out organic phase, extracting water phase with toluene, drying organic phase, filtering, concentrating and drying filtrate under reduced pressure, separating and purifying with silica gel column to obtain compound C02,
x=o, yellow solid, yield 87%, MS (TOF): m/z 655.2325[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.41(1H,s)；8.26～8.22(2H,m)；7.74～7.65(6H,m)；7.63～7.47(6H,m)；7.42～7.36(3H,m)；7.32～7.23(3H,m)；7.04～6.98(3H,m)；6.94～6.83(6H,m)。
Example 2
Preparation of compound C22, taking x=s as an example:
22.0mmol of Int-5' (reactant 1, prepared by the method of synthesis according to example 1), 20.0mmol of sub-2 (reactant 2), 30.0mmol of sodium tert-butoxide are mixed with 60mL of toluene under nitrogen, and 0.2mmol of Pd is added 2 (dba) 3 The catalyst and 0.4mmol Xantphos are heated to 110 ℃ and stirred for reaction for 15 hours, cooled to room temperature, added with 50mL of water, extracted with dichloromethane, collected organic phase is dried, filtered, concentrated and dried under reduced pressure, and separated and purified by a silica gel column to obtain a compound C22;
x=s, yellow solid, yield 82%, MS (TOF): m/z 685.1963[ M+H ] ] + ， 1 HNMR(δ、CDCl 3 )：8.23～8.17(3H,m)；8.01(1H,s)；7.74～7.72(1H,d)；7.61～7.52(5H,m)；7.50～7.45(3H,m)；7.43～7.31(9H,m)；7.28～7.22(3H,m)；7.19～7.14(2H,m)；6.98～6.96(1H,d)。
Example 3
Preparation of compound C98 as x=cme 2 For example, the method comprises the following steps:
the first step: preparation of Compound Int-6
Under the protection of nitrogen, 20.0mmol of A2 (prepared by the synthetic method of A1 in example 1) is dissolved in 60mL of dry THF, the temperature is reduced to minus 78 ℃, 24.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 10 minutes, 30.0mmol of acetone is added dropwise, stirring reaction is carried out for 1 hour, the temperature is raised to room temperature, 50mL of 2M dilute hydrochloric acid aqueous solution is added, ethyl acetate is used for extraction, an organic phase is collected, dried, filtered, filtrate is concentrated to dryness under reduced pressure, and compound Int-6 is obtained by separation and purification by a silica gel column, yellow solid is obtained, and the yield: 86%.
And a second step of: preparation of Compound Int-7
Under the protection of nitrogen, 20.0mmol of Int-6 is dissolved in 60mL of dry dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride diethyl ether is added, the temperature is raised to room temperature, stirring reaction is carried out for 15 hours, 50mL of 5% sodium hydroxide aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected, dried, filtered, and the filtrate is concentrated under reduced pressure to dryness, and is separated and purified by a silica gel column to obtain a compound Int-7, white solid, yield: 90%.
And a third step of: preparation of Compound C98
Under the protection of nitrogen, 22.0mmol of Int-7 (reactant 1), 20.0mmol of sub-3 (reactant 2), 30.0mmol of sodium tert-butoxide and 60mL of xylene are mixed, and then 0.2mmol of Pd is added 2 (dba) 3 The catalyst and 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution are heated to 110 ℃ and stirred for reaction for 15 hours, cooled to room temperature, 50mL of water is added, the mixture is extracted by methylene dichloride, an organic phase is collected and dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the compound C98 is obtained by separating and purifying by a silica gel column;
X＝CMe 2 yellow solid, yield 84%, MS (TOF): m/z 605.2529[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.16～8.12(2H,m)；7.75～7.69(3H,m)；7.65～7.58(4H,m)；7.56～7.48(4H,m)；7.42～7.33(6H,m)；7.25～7.21(3H,m)；7.06～7.02(2H,m)；7.00～6.97(1H,m)；6.93(1H,s)；1.63(6H,s)。
Example 4
The preparation of compound C182, exemplified by x=nph, comprises the following steps:
the first step: preparation of Compound Int-8
Under the protection of nitrogen, 20.0mmol of A3 (prepared by the synthetic method of A1 in example 1) is dissolved in 20mL of o-dichlorobenzene, 0.1mol of triphenylphosphine is added, the temperature is raised to 150 ℃, the mixture is stirred and reacts for 5 hours, the temperature is reduced to room temperature, 50mL of toluene is added, 60.0mmol of anhydrous zinc chloride is added, the mixture is heated to reflux and reacts for 1 hour, the mixture is cooled to room temperature and filtered, a filter cake is washed by methylene dichloride, filtrate is collected and concentrated to dryness under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain a compound Int-8 as yellow solid, and the yield is as follows: 82%.
And a second step of: preparation of Compound Int-9
Under the protection of nitrogen, 20.0mmol of Int-8, 24.0mmol of iodobenzene, 60.0mmol of anhydrous potassium carbonate, 2.0mmol of cuprous iodide and 6.0mmol of N, N' -dimethylethylenediamine are mixed, 80mL of dry toluene is added, the temperature is raised to reflux and stirring for reaction for 15 hours, the temperature is reduced to room temperature, the filtration is carried out, a filter cake is washed by methylene dichloride, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-9 is obtained by separating and purifying by a silica gel column, yellow solid is obtained in a yield: 92%.
And a third step of: preparation of Compound Int-10
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Under the protection of nitrogen, 20.0mmol of Int-9, 24.0mmol of pinacol biborate, 30.0mmol of anhydrous potassium acetate and 2.0mmol of PdCl 2 (dppf) and 2.0mmol of cuprous iodide were mixed, 50mL of dry DMF was added, the temperature was raised to 100℃and stirred for reaction for 15 hours, the temperature was lowered to room temperature, the reaction solution was poured into 150mL of water, filtration was carried out, the filter cake was washed with water, and the solid was separated and purified by a silica gel column to give the compound Int-10 as a yellow solid, yield: 84%.
Fourth step: preparation of Compound C182
Under the protection of nitrogen, 22.0mmol of Int-10 (reactant 1), 20.0mmol of 9- (4- (3-bromophenyl) -6-phenyl-1, 3, 5-triazin-2-yl) carbazole (reactant 2), 80.0mmol of sodium carbonate and 40mL of toluene are mixed, then 0.01mmol of Pd132 catalyst, 20mL of ethanol and 20mL of water are added, the mixture is heated to reflux and stirred for reaction for 12 hours, the mixture is cooled to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by methylene dichloride, the organic phase is collected and dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the compound C182 is obtained by separating and purifying by a silica gel column;
X=nph, yellow solid, yield 87%, MS (TOF): m/z 731.2565[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：9.42(1H,s)；8.95(2H,s)；8.58～8.55(3H,m)；8.31～8.28(1H,m)；8.08～8.06(2H,m)；7.97(1H,s)；7.82～7.78(2H,m)；7.56～7.51(3H,m)；7.46～7.37(7H,m)；7.26～7.22(1H,m)；7.13～7.07(3H,m)；7.05～6.99(4H,m)。
Examples 5 to 204
Referring to the above-described similar synthetic methods, the following compounds of table 1 were prepared:
TABLE 1
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In the above embodiments, X is selected from O, S, CR 9 R 10 Or NR (NR) 11 ；
Wherein R is 9 And R is 10 Methyl, phenyl or fluorenyl, respectively;
R 11 is any one of the following groups:
example 205
An organic electroluminescent device 100, specifically an OLED device, as shown in fig. 1, is a top-emission light device, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, a light emitting layer 106 disposed on the electron blocking layer 105, an electron transport layer 108 disposed on the light emitting layer 106, an electron injection layer 109 disposed on the electron transport layer 108, and a capping layer 111 disposed on a cathode layer 110 and a cathode layer 110 on the electron injection layer 109, wherein the light emitting layer 106 is an organic light emitting layer.
The preparation method of the OLED element comprises the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above processed ITO glass substrate (substrate 101) in vacuum chamber, and vacuumizing to less than 1×10 - 5 Pa, depositing metallic silver as an anode layer 102 on the ITO film, the deposited film thickness beingContinuing to vapor deposit the compounds HI01 and HI02 as the hole injection layer 103, respectively, wherein HI02 is 3% by mass of HI01, and the vapor deposition film thickness is +.>
3) Continuously evaporating a compound HTM as a hole transport layer 104 on the hole injection layer 103 to obtain an evaporated film thickness of
4) Continuously vapor-depositing a compound HT025 as an electron blocking layer 105 on the hole transport layer 104, wherein the vapor-deposited film thickness is equal to
5) The compound of formula (I) of the present invention is further vapor-deposited as a host material and GD010 as a dopant material on the electron blocking layer 105, wherein GD010 is 5% of the mass of the compound of formula (I) as an organic light-emitting layer 106 of the device, and the film thickness of the vapor-deposited organic light-emitting layer 106 is
6) The electron transport layer 108 of LiQ and the compound ET036 is continuously deposited on the organic light-emitting layer 106, wherein the mass of the compound ET036 is 50% of that of LiQ, and the thickness of the deposited film is
7) At the position ofContinuously evaporating a LiF layer on the electron transport layer 108 to form an electron injection layer 109, wherein the film thickness of the evaporated film is
8) A transparent cathode layer 110 of which the element is a metal magnesium and silver deposited on the electron injection layer 109, wherein the mass ratio of magnesium to silver is 1:10, and the thickness of the deposited film is
9) A CPL layer (capping layer 111) of the compound of formula (I) of the present invention as an element is further deposited on the transparent cathode layer 110 to a thickness ofThe OLED element provided by the invention is obtained.
The structures of the compounds used in the examples above were as follows:
example 206
An organic electroluminescent device 100, specifically an OLED device, as shown in fig. 2, is a top-emission light device, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, a light emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the light emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, and a capping layer 111 disposed on a cathode layer 110 and a cathode layer 110 on the electron injection layer 109, wherein the light emitting layer 106 is an organic light emitting layer. The organic electroluminescent device was fabricated by a similar fabrication method as in example 205, except that the evaporation of the hole blocking layer 107 of the compound TPBi as the element was continued on top of the light emitting layer 106 with a thickness of
EXAMPLE 207
An organic electroluminescent device 200 having a structure as shown in fig. 3 and comprising a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, a first light emitting layer 1061, an electron transport layer 108, a charge generation layer 112, a hole injection layer 103, a hole transport layer 104, a second light emitting layer 1062, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer 111 was prepared by a similar method as in example 205. The organic electroluminescent device 200 has a first light emitting layer 1061 and a second light emitting layer 1062, and the light emitting peak shapes of the first light emitting layer 1061 and the second light emitting layer 1062 may be overlapped or cross-overlapped or non-overlapped.
Comparative example 1
According to the same procedure as in example 205, the compound formula of the present invention represented by (I) in step 5) and step 9) was replaced with H01 to obtain comparative element 1.
The driving voltage and current efficiency of the organic electroluminescent elements prepared in example 205 and comparative example 1 and the lifetime of the elements were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was increased at a rate of 0.1V per second, and it was determined that the current density of the organic electroluminescent element reached 10mA/cm 2 The ratio of the brightness to the current density is the current efficiency; at this time, the organic electroluminescent element is placed inside the integrating sphere, and the whole luminous flux of the element is measured; the ratio of luminous flux to current density is the external quantum efficiency. All results are summarized in table 2.
TABLE 2 results of testing the performance of the elements
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Wherein Me is methyl; ph is phenyl; phPh is biphenyl, nap is naphthyl.
As can be seen from the results in table 2, when the compound of the present invention is applied to the OLED light-emitting element as the material of the light-emitting layer and the CPL material, the current efficiency is significantly improved compared with the comparative element 1, and under the same conditions, the external quantum efficiency of the element is significantly improved, and the power consumption of the element at the same brightness is relatively reduced due to the improvement of the efficiency, and the lifetime of the element is also improved. The compound of the invention is an organic electroluminescent material with excellent performance.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. The compound is characterized by having a structural general formula shown in a formula (I):
wherein X is 1 Selected from O, S, CR 9 R 10 Or NR (NR) 11 ；
R 1 、R 11 Each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 5 ～C 50 Arylsilyl groups;
R 2 ～R 10 each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Aryl silyl group, any adjacent two or more R 2 ～R 10 Optionally joined or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
and at R 2 ～R 8 At least one of which is a group of formula (II);
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine groups;
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
* -a linking site representing a group.
2. The compound of claim 1, wherein the compound is selected from the group consisting of:
wherein R is 1 ～R 7 、X 1 、L 1 、Ar 1 And Ar is a group 2 Is as defined in claim 1;
each m is independently selected from 0, 1 or 2.
3. According toThe compound of claim 1, wherein R 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, or formula (II);
R 2 ～R 8 Each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen atoms, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylA group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, or a compound of formula (II)Group, and, at R 2 ～R 8 At least one of which is a group of formula (II);
R 9 、R 10 each independently selected from the group consisting of hydrogen, methyl, ethyl, phenyl, fluorenyl;
Ar 1 、Ar 2 、R 11 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenyl A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophene group.
4. The compound of claim 1 or 2, wherein the heteroaryl is selected from the group consisting of the groups shown in II-1 to II-13:
wherein,,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 Representation O, S or NAr ’ ；
Ar ’ Selected from C 1 ～C 40 Alkyl, C of (2) 1 ～C 40 Heteroalkyl 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 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups; preferably Ar ’ Methyl, ethyl, phenyl, biphenyl or naphthyl;
representing the attachment site of the group.
5. A compound according to any one of claims 1 to 3, wherein L 1 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
wherein X is selected from O, S, se, CR ’ R”、SiR ’ R' or NAr ’ ；
Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
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; y5 represents an integer of 1 or 2;
R ’ R' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl 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 formed; preferably, R ’ R' is methyl, phenyl or fluorenyl;
Ar ’ selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (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 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably Ar ’ Is methyl, ethylA group, phenyl, biphenyl, or naphthyl;
wherein the dotted line represents the attachment site of the group.
6. A compound according to any one of claims 1 to 5, wherein the compound is selected from one or more of the following C01 to C204 structures:
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wherein X is selected from O, S, CR 9 R 10 Or NR (NR) 11 ；
The R is 9 And R is 10 Methyl, phenyl or fluorenyl, respectively;
the R is 11 Selected from the group consisting of:
7. An organic electroluminescent material, characterized in that it comprises a compound according to any one of claims 1 to 6.
8. An organic electroluminescent device comprising a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer or the capping layer comprises the compound of any one of claims 1-6.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a charge generation layer; wherein each organic layer is one, two or more layers;
preferably, the light-emitting layer, the capping layer or the charge generating layer comprises the compound according to any one of claims 1 to 6.
10. A consumer product comprising the organic electroluminescent device of any one of claims 8-9.
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