CN115010736A - Polar boron-nitrogen luminescent material, application thereof and organic electroluminescent device comprising same - Google Patents
Polar boron-nitrogen luminescent material, application thereof and organic electroluminescent device comprising same Download PDFInfo
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- CN115010736A CN115010736A CN202210679145.3A CN202210679145A CN115010736A CN 115010736 A CN115010736 A CN 115010736A CN 202210679145 A CN202210679145 A CN 202210679145A CN 115010736 A CN115010736 A CN 115010736A
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- quinolyl
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- 239000000463 material Substances 0.000 title claims abstract description 79
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 229910052796 boron Inorganic materials 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- -1 cyano, amino Chemical group 0.000 claims description 207
- 239000010410 layer Substances 0.000 claims description 103
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 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 8
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 8
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 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 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 6
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 6
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 6
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 6
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 6
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 6
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 5
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002346 layers by function Substances 0.000 claims description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 8
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- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 32
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- 239000002904 solvent Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
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- 239000000741 silica gel Substances 0.000 description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- 238000004519 manufacturing process Methods 0.000 description 14
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- 238000001228 spectrum Methods 0.000 description 14
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
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- 239000002244 precipitate Substances 0.000 description 11
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
The invention relates to a polar boron-nitrogen luminescent material, in particular to a resonance type organic compound, application thereof and an organic electroluminescent device containing the compound. The light-emitting material has a structure as follows. Wherein Y represents N or B, ring A, ring B, ring C, ring D, ring E and ring F each independently represent one of aromatic ring of C6-C20 and heteroaromatic ring of C5-C20, N1, N2 and N3 are each independently 0 or 1, X is 1 、X 2 And X 3 Each independently selected from the group consisting of a single bond and CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O or S (O) O, S, C 2 . The compound B-N polar bond doped into the MR resonance framework has obvious advantages in photoelectric properties as a luminescent material, and has the advantages of obviously adjusting light color, improving quantum yield and prolonging service life of the device when being used as the luminescent material in an OLED device.
Description
Technical Field
The invention relates to a luminescent material, belongs to the technical field of organic electroluminescence, and particularly relates to a resonance type organic compound, application thereof and an organic electroluminescent device containing the compound.
Background
With the continuous progress of technology and the rapid development of information display, display technologies are undergoing a step-by-step move from high-definition display to ultra-high-definition display (UHD), and promoting digital transformation of industries with display as a core. The new generation ultra high definition video production and display system bt.2020 redefines the CIE color coordinates of the three primary colors red (0.708, 0.292), green (0.170, 0.797), blue (0.131, 0.046), and has a color gamut space much higher than 35.9% of that of the conventional high definition display bt.709. However, achieving a wide gamut space requires narrow-spectrum luminescent materials with high color purity, which poses new challenges for the study of luminescent materials, in particular tri-phosphor luminescent materials with a full width at half maximum (FWHM) < 30 nm. Currently, although organic light-emitting diode (OLED) technology has been commercialized, the FWHM of the existing commercialized luminescent materials (fluorescent and phosphorescent materials) is generally wide (>40nm), and an optical filter or a microcavity structure is required to adjust the spectrum, which greatly reduces the brightness and the luminous efficiency of the device, and hinders the development of the ultra-high-definition OLED display technology. Therefore, designing and developing a narrow-spectrum luminescent material system that can achieve high efficiency and high color purity under intrinsic conditions is a crucial and challenging scientific problem to achieve ultra-high-definition display technology of OLEDs.
In the method for solving the problem of wide half-peak width of the organic light-emitting material, the Hatakeyama research group proposed in 2016 to construct a novel polycyclic rigid framework strategy with Multiple Resonance (MR) effect, and the strategy has attracted extensive attention in the scientific research field and the industrial field. The most attractive MR material is blue organic luminescent material v-DABNA which is successfully developed by the research group in 2019 by utilizing boron-nitrogen resonance effect and has color purity exceeding that of gallium nitride and quantum dot series, the half-peak width of an electroluminescent device is only 18nm, and the maximum external quantum efficiency reaches 34.4%. However, despite the great progress made in recent years in the development of narrow-spectrum light-emitting materials based on such B, N resonance skeleton system and the demonstration that such materials are an effective strategy for realizing high-efficiency, full-color, narrow-spectrum organic light-emitting materials, there are still many problems to be solved, such as single molecular design and difficult synthesis. On one hand, the structural design of the luminescent material is relatively single, so that the number of MR material systems capable of realizing narrow-spectrum emission in a full-color range is still small, and meanwhile, the relationship between the structural design of the material and the FWHM needs to be further researched; more importantly, the boronizing reaction conditions of the MR materials are harsh, multiple reaction steps are required, the yield is low, and the mass production is difficult. This greatly limits the industrial development of narrow-spectrum OLED materials.
Compared with the B and N doped polycyclic aromatic hydrocarbon compound, the B-N polar bond doped conjugated system is constructed by replacing carbon-carbon double bonds (C ═ C) in the polycyclic aromatic hydrocarbon skeleton with isoelectric boron-nitrogen bonds (B-N), the development process is earlier, the synthetic method is simpler, and the B-N polar bond doped conjugated system becomes one of effective strategies for enriching and innovating organic functional materials. The fused ring aromatic hydrocarbon compound doped with the B-N covalent bond has a framework similar to that of a pure carbon aromatic hydrocarbon derivative and shows unique photoelectric properties. Dipolar action such as B-N regulates the molecular arrangement of pi-conjugated systems and excellent hole (electron) mobility, making it widely used in organic field-effect transistors (OFETs) and organic photovoltaic devices (OPVs). In addition, B-N doped fused ring aromatic compounds were also used primarily in OLEDs, confirming the feasibility of this class of materials for use in electroluminescent devices. Therefore, the development of the ultra-high-definition display technology based on the luminescent material doped with the B-N polar bond has unique advantages and strong attraction on the display index of BT.2020.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides a resonance type organic compound and applications thereof. The skeleton represented by the general formula (1) is a B-N covalent bond doped MR resonance skeleton, and an organic narrow-spectrum luminescent material with a new structure is constructed. The B-N polar bond doped into the MR resonance framework as a luminescent material has obvious advantages in photoelectric property, and has the functions of obviously adjusting light color, improving quantum yield and prolonging the service life of a device.
The technical scheme of the invention is as follows: a light-emitting material has a general structural formula shown in general formula (1):
in the formula (1), the dotted line represents connection or non-connection;
y represents N or B;
ring A, ring B, ring C, ring D, ring E, and ring F each independently represent any of an aromatic ring of C6 to C20 and a heteroaromatic ring of C5 to C20;
n1, n2, n3 are each independently 0 or 1;
X 1 、X 2 and X 3 Each independently selected from the group consisting of a single bond and CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O or S (O) O, S, C 2 ；
Preferably, said X 1 、X 2 And X 3 Are respectively a single bond at the same time; or, when X 1 And X 3 While being a single bond, X 2 Is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S; or, when X 1 And X 3 At the same time is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S when one of them is selected from the group consisting of 2 Is a BR 4 ；
The R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from one of the following substituted or unsubstituted groups: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamine, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 fused ring heteroaryl;
R a 、R b 、R c 、R d 、R e 、R f and R g Each independently represents a single substituent up to the maximum allowed number of substituent groups and each is independently selected from hydrogen, deuterium, halogen, or one of the following substituted or unsubstituted groups: one of chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitryl, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and monoheteroaryl of C5-C60; r g One selected from arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and heteroaryl of C5-C60; and said R is a 、R b 、R c 、R d 、R e 、R f And R g May be connected to each other by a single bond or may be fused to form a ring;
when the above R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R a 、R b 、R c 、R d 、R e And R f When the substituent exists, the substituent groups are respectively and independently selected from any one of deuterium, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroaryl of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 and fused ring heteroaryl of C5-C60.
Preferably, the specific general formula of the compound of the present invention is represented by any one of the following formulas (2), (3), (4), (5), (6) and (7):
in the formulae (2), (3), (4), (5), (6) and (7), X is 1 、X 2 、X 3 、n1、n2、n3、R a 、R b 、R c 、R d 、R e 、R f And R g Are the same as defined in formula (1).
More preferably, in the formulae (2), (3), (4), (5), (6) and (7), X is 2 Is a single bond, n2 is 0 or 1; or, the X 1 、X 2 And X 3 Are respectively a single bond at the same time; or, when X 1 And X 3 While being a single bond, X 2 Is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S; or, when X 1 And X 3 At the same time is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 And O, S, X 2 Is BR 4 。
Preferably, the specific general formula of the compound of the present invention is the structure represented by the following formula (8) or formula (9):
in the formulae (8) and (9), the dotted line represents a connection or non-connection; x 1 、X 2 、X 3 、n1、n2、n3、R a 、R c 、R d 、R e 、R f And R g Are all as defined in formula (1);
preferably, in formula (8) and formula (9), the dotted line represents a linkage;
preferably, in the formulae (8) and (9), X is 2 Is a single bond, n2 is 0 or 1; or, the X 1 、X 2 And X 3 Are respectively a single bond at the same time; or, when X 1 And X 3 While being a single bond, X 2 Is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S; or, when X 1 And X 3 At the same time being CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 And O, S, X 2 Is a BR 4 。
More preferably, in the formulae (1) to (9), the ring a, the ring B, the ring C, the ring D, the ring E and the ring F each independently represents any one of an aromatic ring of C6 to C10 and a heteroaromatic ring of C5 to C10; more preferably, the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from one of a benzene ring and a naphthalene ring; or preferably, the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from one of a benzene ring, a naphthalene ring or a pyridine ring.
Preferably, in the formulae (1) to (9), R a 、R b 、R c 、R d 、R e 、R f And R g Each independently selected from one of hydrogen, deuterium, halogen, chain alkyl of C1-C6, cycloalkyl of C3-C6, alkoxy of C1-C6, thioalkoxy of C1-C6, cyano, arylamino of C6-C20, heteroarylamino of C3-C20, aryl of C6-C30, aryloxy of C6-C30 and heteroaryl of C5-C30; the R is a 、R b 、R c 、R d 、R e 、R f And R g May be connected to each other by a single bond or may be fused to form a ring;
further said R a 、R b 、R c 、R d 、R e 、R f Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, furanyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, 2, 2-trifluoroethyl, phenyl, 2-anthyl, phenyl, anthryl, phenanthryl, terphenyl, terp, Benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, substituted or unsubstituted alkyl,Isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthrimidazolyl, pyridoimidazolyl, pyrazinoiyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrdazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthrenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazenylene group, 1, 8-diazenylene group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silyl, or a combination of two substituents selected from the above;
more preferably, R is a 、R b 、R c 、R d 、R e 、R f Each independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furyl, benzofurylIsobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthrimidazolyl, pyridoimidazolyl, pyrazinimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthryl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4, 5-diazenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 3-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, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, indolizinyl, benzothiazolyl, 9-dimethylazinyl, 1,2, 3-triazolyl, 1,2, 4-triazinyl, 1, 3-triazinyl, 1,2, 3-triazinyl, 1, 4, 5-tetrazinyl, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, and the like, Triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy or silyl groups.
Further preferably, in the formulae (1) to (9), R is g Selected from phenyl, naphthyl, anthryl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, n-hexyl, cyclohexyl, neohexyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecylindenylSpirotrimeric indenyl, spiroisocyclopentanyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalyl, 1, 5-diazoanthrenyl, 2, 7-diazepine, 2, 3-diazepine, 1, 6-diazenylene group, 1, 8-diazenylene group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, and silyl.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when the number of substituents is plural (at least 2), the same or different substituents may be present; when the same expression is referred to below, the same meanings are given, and the selection ranges of the substituents are as shown above, and are not repeated.
In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The same description is referred to hereinafter, all having the same meaning.
In the present invention, unless otherwise specified, the expression of chemical elements includes the concept of isotopes having the same chemical properties, and for example, hydrogen (H) includes 1H (protium), 2H (deuterium, D), 3H (tritium, T), and the like; carbon (C) includes 12C, 13C, etc.
In the present invention, unless otherwise specified, the hetero atom of the heteroaryl group is selected from N, O, S, P, B, Si or Se.
In the present invention, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
In the present invention, the expression of Ca to Cb means that the group has carbon atoms a to b, and the carbon atoms do not include the carbon atoms of the substituents unless otherwise specified.
In the present invention, "independently" means that the subject may be the same or different when a plurality of subjects are present.
In the present invention, each of C6 to C60 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, or the like.
Each of C3 to C60 may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58.
The C1 to C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or the like.
The C3 to C20 may be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or the like.
The C1 to C36 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C25, C28, C30, C32, C34, C35, or the like.
The C3 to C20 may be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, or the like.
The C1-C10 can be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10.
The C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28.
The C3 to C30 may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, or the like.
In the present invention, the C6-C60 aromatic ring, preferably C6-C30 aromatic ring, and more preferably C6-C20 aromatic ring include both single aromatic ring and fused aromatic ring; the single aromatic ring includes a benzene ring, and the fused aromatic ring means that at least 2 aromatic rings are contained in the ring and the aromatic rings are fused to each other with two adjacent carbon atoms in common, and exemplarily include but are not limited to: naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring and derivatives thereof (9, 9-dimethylfluorene ring, 9-diphenylfluorene ring, 9-dinaphthylfluorene ring, spirobifluorene ring, benzofluorene ring and the like), fluoranthene ring, triphenylene ring, pyrene ring, perylene derivative, and the like,
Cyclic or acenaphthyl rings, and the like.
The C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, and more preferably a C3-C20 heteroaromatic ring, and comprises a single heteroaromatic ring or a fused heteroaromatic ring. Exemplary single heteroaromatic rings include, but are not limited to: a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a thiophene ring, a pyrrole ring, etc. The fused heteroaromatic ring means a ring structure having at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) fused to each other with two adjacent atoms in common, and includes, but is not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring and derivatives thereof (N-phenylcarbazole ring, N-naphthylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolocarbazole ring, azacarbazole ring and the like), acridine ring, phenothiazine ring, phenoxazine ring, hydrogenated acridine ring and the like.
The C6-C60 aryl group, preferably C6-C30 aryl group, more preferably C6-C20 aryl group, comprises monocyclic aryl group and thick aryl groupA cyclic aryl group; the monocyclic aryl group means that the group contains at least 1 phenyl group, and when the group contains at least 2 phenyl groups, the phenyl groups are connected to each other by a single bond, and exemplarily includes, but is not limited to: phenyl, biphenyl, terphenyl, and the like; the fused ring aryl means a group in which at least 2 aromatic rings are contained in a group and two adjacent carbon atoms are shared between the aromatic rings to be fused with each other, and exemplary include, but are not limited to: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof (9, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), anthryl, triphenylenyl, pyrenyl, perylenyl, perylene, etc,
Phenyl or tetracenyl, and the like.
The heteroaryl of C3-C60, preferably C3-C30, and more preferably C3-C20, includes monocyclic heteroaryl or fused ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl, and when the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are connected by a single bond, and exemplarily includes but is not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl and the like. The fused-ring heteroaryl means a group which has at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in a molecule and two adjacent atoms are fused with each other, and exemplarily includes but is not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and derivatives thereof (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroazocinyl, etc.
The C1 to C36 chain alkyl group specifically includes a straight chain or branched chain alkyl group, preferably a C1 to C20 straight chain or branched chain alkyl group, more preferably a C1 to C16 straight chain or branched chain alkyl group, still more preferably a C1 to C10 straight chain or branched chain alkyl group, and exemplarily includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.
The C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, illustratively includes but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
The C3-C20 heterocycloalkyl group, more preferably C3-C10 heterocycloalkyl group, i.e., a group formed by replacing at least 1 carbon atom of the above-listed cycloalkyl groups with a heteroatom (e.g., O, S or N, etc.), illustratively including but not limited to: tetrahydropyrrolyl, tetrahydrofuryl, tetrahydrothienyl, piperidinyl, dioxanyl, and the like.
In the present invention, the aryloxy group is a monovalent group composed of the above-mentioned aryl group and oxygen, and the heteroaryloxy group is a monovalent group composed of the above-mentioned heteroaryl group and oxygen.
Further, the compounds described in the general formula (1) of the present invention may preferably be compounds 1 to 322 of the following specific structures, which are merely representative:
the present invention also provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any one of the above general formulae (1) to (9), or the organic layer comprises any one of the above compounds 1 to 322.
Specifically, embodiments of the present invention provide an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; among them, it is preferable that the light-emitting layer contains the compound represented by the general formula of the present invention represented by any one of the general formulae (1) to (9).
The general formula compound (shown in the following formula) of the invention adopts a B-N covalent bond to dope an MR resonance framework to construct a novel organic narrow-spectrum luminescent material, the embedding of the B-N bond maintains the planar structure of the MR framework, and unique photophysical properties such as bipolar carrier transmission capability, intermolecular dipole-dipole interaction and the like are obtained. The material has advantages in synthesis, the target material is synthesized by a three-step method, the boronization reaction condition is simple, the yield is higher and reaches more than 90 percent, and compared with the traditional boronization reaction, the compound provided by the invention is more beneficial to realizing large-scale production; secondly, the structure of the material is optimized through a mother nucleus, a peripheral substituent group, a condensed ring parallel connection mode and the like, the full width at half maximum (FWHM) of a fluorescence spectrum of the material is only 26-32nm, PLQY is more than 90%, and the material has high brightness.
Specifically, ring a, ring B, ring C, ring D, ring E, ring F in the general formula of the present invention may each independently be selected from one of groups such as a benzene ring, a naphthalene ring, and an aza-condensed ring, and when introduced into the general formula of the compound of the present invention, the compound of the present invention has significant adjustment of the photo-physical properties such as red-shift and blue-shift of absorption and emission, although these groups have different electron donating or electron withdrawing abilities. Because the molecular structure of the compound has a rigid pi-conjugated plane and the luminescence of molecules mainly comes from short-range intramolecular charge transfer, the ring A-F has small influence on the half-peak width and photoluminescence quantum efficiency of the compound, and can obtain ideal photophysical properties. In combination with more preferred embodiments, such as X 1 、X 2 And X 3 When they are single bonds at the same time; when peripheral groups are all carbazole groups, because the carbazole groups have relatively weak electron-donating capability, excited state electrons of the series of compounds are delocalized on the whole conjugated plane, and the luminous performance and stability of the material are greatly improved. As another example, in parallel, when X 1 And X 3 At the same time being CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S, X 2 Is B R 4 . It is particularly emphasized that X 2 Is B R 4 In the invention, the central skeleton of the compound forms a triangular plane configuration surrounded by three boron atoms, and the hollow p-orbit of the boron center can be effectively conjugated with adjacent heterocyclic rings such as benzene rings and the like, so that the photoelectric property of the material is greatly improved; and when Y is a nitrogen atom, the Y and the nitrogen atom can form an effective multiple resonance effect, so that the half-peak width of the luminescent material is effectively narrowed.
In the general formula of the invention, Y is selected from N or B respectively, and as mentioned above, when Y is a nitrogen atom, the half-peak width of the luminescent material can be effectively narrowed; when Y is a boron atom, the central skeleton of the compound of the invention contains three boron atoms, which can enhance the electron-deficient property of the central skeleton, and when X is arranged at the periphery 1 And X 3 At the same time is CR 1 R 2 、NR 3 、SiR 5 R 6 O, S, a short-range intramolecular charge transfer process can be formed in the molecule, the material shows low polarity, and in combination with a rigid molecular plane structure, the compound of the invention can also keep narrower half-peak width of light emission, and simultaneously the energy difference between the excited singlet state and the excited triplet state with the lowest energy can be reduced, thereby being beneficial to the reverse system crossing of the lowest triplet state exciton and improving the thermal activation delayed fluorescence property. In conclusion, the compound combines the boron-nitrogen polar bond with unique photophysical property and the boron-nitrogen structure with multiple resonance effect, realizes a simple, efficient and large-scale preparation way of a synthetic method, provides direction for the development and commercialization of multiple resonance narrow spectrum materials, greatly enriches the framework system of the multiple resonance narrow spectrum materials, and has great hope of obtaining the three-primary-color narrow spectrum organic luminescent material with high color purity and high efficiency by screening.
The OLED device prepared by the compound has narrow half-peak width and shows obvious multiple resonance effect, thereby greatly enriching a material system of multiple resonance-thermal activation delayed fluorescence, greatly optimizing the synthesis process and improving the reaction yield; in the aspect of OLED devices, the OLED device has low starting voltage, high luminous efficiency and better service life, can meet the requirements of current panel manufacturing enterprises on high-performance materials, and shows good application prospects.
Drawings
FIG. 1: the electroluminescence spectrum of the organic electroluminescent device D1 prepared by the embodiment of the invention is shown in the figure.
FIG. 2: the structure of the organic electroluminescent device prepared by the invention is shown in the figure, wherein 1 is a substrate, 2 is an anode, 3 is a hole transport layer, 4 is an organic luminescent layer, 5 is an electron transport layer, and 6 is a cathode.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
Basic chemical raw materials of various chemicals used in the present invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N-diisopropylethylamine, reaction intermediate, and the like, are commercially available from shanghai tatarian technologies ltd and silong chemical ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthesis method of the compound of the present invention is briefly described below, and the intermediate compound (1) is obtained by nucleophilic substitution reaction, the intermediate (2) is obtained by suzuki coupling reaction after adding the boron ester, and the target compound is obtained by amino-directed electrophilic boronation reaction.
Example 1 synthesis of compound 4:
preparation of intermediate B1:
to a three-necked flask, the starting material A1(10mmol), 50mL anhydrous DMF was added in this order, and nitrogen was used for protectionAdding Cs 2 CO 3 (40mmol), carbazole (20mmol), and the mixture was heated and stirred for 24 hours. After the reaction, 100mL of water was added to quench the reaction, and a large amount of white precipitate was filtered off. The precipitate was collected and dried over anhydrous sodium sulfate, filtered, and concentrated to a solid, and passed through a silica gel column using petroleum ether: purification with 500:1 developing solvent afforded intermediate B1. LC-MS: measurement value: 566.97([ M + H)] + ) The theoretical value is as follows: 565.98.
preparation of intermediate C1:
in a two-necked flask, the intermediate B1 compound (3.6mmol) was dissolved in 30mL of a mixed solution of dimethyl ether and water (3:1) under a nitrogen atmosphere. Diphenyleneboronic ester (8.7mmol), potassium carbonate (36.2mmol) and tetrakis (triphenylphosphine) palladium (0.36mmol) are added, and then the temperature is raised to 80 ℃ in sequence for reaction for 16 hours. Vacuum spin-drying solvent, passing through silica gel column (developing agent: petroleum ether: CH) 2 Cl 2 10:1) to give the target intermediate C1(2.8g, 81% yield, HPLC assay purity 99.65%) as a yellow solid. LC-MS: measurement value: 948.48([ M + H)] + ) The theoretical value is as follows: 947.51
Preparation of compound 4:
intermediate C1(0.8mmol) was dissolved in 30ml of chlorobenzene, and boron tribromide (3.3mmol) and triethylamine (8.1mmol) were added thereto, and the reaction was allowed to proceed for 18 hours at 150 ℃. Vacuum spin-drying solvent, passing through silica gel column (developing agent: petroleum ether: CH) 2 Cl 2 10:1) to give the target compound 4 (91% yield, 99.22% analytical purity by HPLC) as a yellow solid. 1 H NMR(600MHz,Methylene Chloride-d 2 )δ(ppm):8.95(d,J＝7.4Hz,2H),8.52(d,J＝8.5Hz,2H),8.35(d,J＝8.4Hz,2H),8.19(d,J＝7.3Hz,2H),8.08(d,J＝2.1Hz,2H),8.02(d,J＝1.7Hz,2H),7.55(t,J＝7.4Hz,2H),7.49(dd,J＝8.5,2.0Hz,2H),7.31(d,J＝7.4Hz,2H),7.24–7.18(m,2H),7.12(d,J＝8.2Hz,2H),6.64(d,J＝1.7Hz,2H),1.47(s,18H),0.73(s,18H). 13 C NMR(151MHz,Methylene Chloride-d 2 )δ(ppm):145.56,141.44,139.57,132.41,126.49,126.48,126.19,124.98,124.96,124.65,124.63,123.88,122.98,122.40,121.05,120.50,117.87,116.85,115.70,53.81,53.64,53.46,53.27,53.09,34.89,34.88,34.54,34.53,31.62,31.61,30.89,30.88.MALDI-TOF:Calculated:978.0432,Found:978.1663.
Example 2 synthesis of compound 129:
preparation of intermediate B2:
to a three-necked flask, the starting material A1(10mmol), 50mL anhydrous DMF was added sequentially, and Cs was added using nitrogen blanket 2 CO 3 (40mmol), 3, 6-di-tert-butylcarbazole (20mmol), and the mixture was heated and stirred for 24 hours. After the reaction, 100mL of water was added to quench the reaction, and a large amount of white precipitate was filtered off. The precipitate was collected and dried over anhydrous sodium sulfate, filtered, and concentrated to a solid, and passed through a silica gel column using petroleum ether: purification with 500:1 developing solvent afforded intermediate B2. LC-MS: measurement value: 791.63([ M + H)] + ) The theoretical value is as follows: 790.73.
preparation of intermediate C2:
in a two-necked flask, the intermediate B2 compound (3.6mmol) was dissolved in 30mL of a mixed solution of dimethyl ether and water (3:1) under a nitrogen atmosphere. Diphenyleneboronic ester (8.7mmol), potassium carbonate (36.2mmol) and tetrakis (triphenylphosphine) palladium (0.36mmol) are added, and then the temperature is raised to 80 ℃ in sequence for reaction for 16 hours. Vacuum spin-drying solvent, passing through silica gel column (developing agent: petroleum ether: CH) 2 Cl 2 10:1) to give the target intermediate C1(2.8g, 81% yield, HPLC assay purity 99.65%) as a yellow solid. LC-MS: measurement value: 948.48([ M + H)] + ) The theoretical value is as follows: 947.51
Preparation of compound 129:
intermediate C2(0.8mmol) was dissolved in 30ml of chlorobenzene, and boron tribromide (3.3mmol) and triethylamine (8.1mmol) were added thereto, and the temperature was raised to 150 ℃ to react for 18 hours. Vacuum spin-drying solvent, passing through silica gel column (developing agent: petroleum ether: CH) 2 Cl 2 10:1) to give the target compound 4 (91% yield, 99.22% analytical purity by HPLC) as a yellow solid. 1 H NMR(400MHz,Methylene Chloride-d 2 )δ(ppm):9.18(d,J＝1.5Hz,2H),8.87(d,J＝8.2Hz,2H),8.72(d,J＝1.7Hz,2H),8.41(d,J＝1.8Hz,2H),8.14(dd,J＝7.5,1.1Hz,2H),7.98(d,J＝7.1Hz,2H),7.63(t,J＝7.2Hz,2H),7.49(t,J＝7.4Hz,2H),7.22(dd,J＝8.7,1.8Hz,2H),6.88(d,J＝8.4Hz,2H),6.78–6.70(m,2H),6.38(d,J＝8.3Hz,2H),1.65(s,18H),1.43(s,18H). 13 C NMR(101MHz,Methylene Chloride-d 2 )δ(ppm):145.76,143.33,143.20,142.93,142.02,141.88,137.62,129.83,129.04,126.39,126.21,125.80,124.82,123.51,122.64,122.33,120.91,120.81,120.63,116.84,116.44,109.74,54.01,53.74,53.47,53.20,52.93,35.69,34.74,32.08,31.79.MALDI-TOF:Calculated:978.5004,Found:978.1663.
Example 3 synthesis of compound 110:
synthesis of intermediate B3:
synthesis of intermediate B3 reference intermediate B1, except that diphenylamine was used in place of carbazole to give intermediate B3. LC-MS: measurement value: 480.21([ M + H)] + ) The theoretical value is as follows: 479.21.
synthesis of intermediate C3:
synthesis of intermediate C3 reference intermediate C2, except intermediate B3 was used instead of intermediate B2 to afford intermediate C3. LC-MS: measurement value: 652.83([ M + H)] + ) The theoretical value is as follows: 651.81.
synthesis of intermediate C3 a:
synthesis of intermediate C3a synthesis of reference compound 129 was performed with the exception that intermediate C3 was used instead of intermediate C2 to give intermediate C3 a. LC-MS: measurement value: 668.30([ M + H)] + ) The theoretical value is as follows: 663.35.
synthesis of compound 110:
the intermediate C3a was dissolved in 30mL of dichloromethane, trifluoromethanesulfonic acid and dichlorodicyanobenzoquinone were added, the reaction was quenched after 1 hour of reaction with 100mL of water, and the large amount of white precipitate that separated out was filtered. Collecting precipitate, drying with dichloromethane solution, drying with anhydrous sodium sulfate, filtering, concentrating the reaction solution, passing through silica gel column, and collecting petroleumEther: purification with 500:1 developing solvent gave compound 110. LC-MS: measurement value: 668.24([ M + H)] + ) The theoretical value is as follows: 667.38.
example 4 synthesis of compound 113:
synthesis of intermediate B4:
synthesis of intermediate B4 reference intermediate B1, except that phenoxazine was used instead of carbazole to give intermediate B4. LC-MS: measurement value: 494.29([ M + H)] + ) The theoretical value is as follows: 493.21.
synthesis of intermediate C4:
synthesis of intermediate C4 reference intermediate C2, except intermediate B4 was used instead of intermediate B2 to afford intermediate C4. LC-MS: measurement value: 666.86([ M + H)] + ) The theoretical value is as follows: 665.79.
synthesis of compound 113:
synthesis of compound 113 reference was made to the synthesis of compound 129 except intermediate C4 was used instead of intermediate C2 to afford compound 113. LC-MS: measurement value: 682.39([ M + H)] + ) The theoretical value is as follows: 681.37.
example 5 synthesis of compound 195:
synthesis of intermediate B5:
a two-necked flask was charged with raw material A3(10.0mmol), raw material A4(10.0mmol), and Pd (PPh) in this order 3 ) 4 Catalyst (0.1mmol), 50mL tetrahydrofuran: water 10:1 mixed solution, potassium carbonate (20mmol), followed by nitrogen blanket, stirred at 80 ℃ for 7.5 hours, cooled, separated and the organic phase collected, dried over anhydrous sodium sulfate and filtered and concentrated, passed through a silica gel column with petroleum ether: the compound was isolated with ethyl acetate 5:1 as a developing solvent to give intermediate B5. LC-MS: measurement value: 363.15([ M + H)] + ) The theoretical value is as follows: 362.11.
synthesis of intermediate B6:
to a two-necked flask were added in this order intermediate B5(10.0mmol), triethylphosphino (20.0mmol), followed by nitrogen protection, stirring under reflux for 24 hours, cooling and concentrating the reaction solution, which was purified by passing through a silica gel column with petroleum ether: the compound was isolated with ethyl acetate 100:1 as the developing solvent to give intermediate B16. LC-MS: measurement value: 331.18([ M + H)] + ) The theoretical value is as follows: 330.12.
preparation of intermediate B7:
synthesis of intermediate B16 reference intermediate B2, except that intermediate B6 was used instead of 3, 6-di-tert-butylcarbazole, giving intermediate B7. LC-MS: measurement value: 641.35([ M + H)] + ) The theoretical value is as follows: 640.38.
preparation of intermediate C5:
synthesis of intermediate C5 reference intermediate C2, except that intermediate B7 was used instead of B2 to afford intermediate C5. LC-MS: measurement value: 1038.26([ M + H)] + ) The theoretical value is as follows: 1047.31.
preparation of compound 195:
this example is essentially the same as the synthesis of compound 129, except that in this example the illustrated reactants have to be replaced. Target compound 195(0.6g, 86% yield, 99.56% purity by HPLC) as a yellow solid. LC-MS: measurement value: 1053.88([ M + H)] + ) The theoretical value is as follows: 1052.98.
example 6 synthesis of compound 272:
preparation of intermediate B8:
charging raw material A11(10.0mmol), anhydrous DMF40mL and NaH (11.0mmol) into a two-necked flask in this order, stirring at room temperature for 1 hour, subsequently charging raw material A12(10mmol) dissolved in 10mL of anhydrous DMF, stirring at room temperature for 6 hours, charging 100mL of water, precipitating a large amount of white solid, filtering, taking the precipitate to dissolve with dichloromethane, drying and filtering with anhydrous sodium sulfate,the organic phase was concentrated, passed through a silica gel column and purified with petroleum ether: ethyl acetate 50:1 as developing solvent the compound was isolated to give intermediate B18. LC-MS: measurement value: 489.03([ M + H)] + ) The theoretical value is as follows: 487.95.
preparation of intermediate B9:
the intermediate B18(5.0mmol), N-dimethylformamide (DMAc)50mL, palladium acetate (0.5mmol), potassium carbonate (25.0mmol), tetra-N-butylammonium bromide (2.5mmol) and triphenylphosphine (5mmol) were sequentially added to a two-necked flask, and the mixture was heated under reflux and stirred for 22 hours, and the reaction mixture was concentrated by filtration, and the compound was isolated by a silica gel column using petroleum ether as a developing agent to obtain intermediate B19. LC-MS: measurement value: 409.12([ M + H)] + ) The theoretical value is as follows: 408.03.
preparation of intermediate B10:
in a three-necked flask, under the protection of nitrogen, intermediate B9(10mmol), pinacol diborate (20mmol), potassium acetate (30mmol), S-phos (2mmol), Pd 2 (dba) 3 (0.4mmol) was added to 250mL dioxane and refluxed for 7h, the reaction was cooled to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by silica gel column chromatography using n-heptane/ethyl acetate (9:1) as eluent to give intermediate B10. LC-MS: measurement value: 330.33([ M + H)] + ) The theoretical mass is as follows: 329.38.
preparation of intermediate B11:
synthesis of intermediate B11 reference intermediate C2, except intermediate B10 was used instead of intermediate B2 to afford intermediate B11. LC-MS: measurement value: 776.76([ M + H ]] + ) The theoretical value is as follows: 776.82.
preparation of intermediate C6:
synthesis of intermediate C6 reference intermediate C2, except intermediate B11 was used instead of intermediate B2 to afford intermediate C6. LC-MS: measurement value: 864.05([ M + H)] + ) The theoretical value is as follows: 863.12.
preparation of compound 272:
preparation of compound 272 reference compound 129 was made except intermediate C6 was used instead of intermediate C2 to give compound 272.LC-MS: measurement value: 879.55([ M + H)] + ) The theoretical value is as follows: 878.69.
example 7 synthesis of compound 281:
preparation of intermediate B12:
a raw material A8(5.0mmol), N-dimethylformamide (DMAc)50mL, palladium acetate (0.5mmol), potassium carbonate (25.0mmol), tetra-N-butylammonium bromide (2.5mmol) and triphenylphosphine (5mmol) were sequentially added to a two-necked flask, and the mixture was heated under reflux and stirred for 25 hours, and the reaction mixture was filtered and concentrated to separate the compound by means of a silica gel column using petroleum ether as a developing agent, thereby obtaining an intermediate B12. LC-MS: measurement value: 242.11([ M + H)] + ) The theoretical value is as follows: 241.09.
preparation of intermediate B13:
intermediate B12(10.0mmol), NBS (20.0mmol), and anhydrous DMF 7mL were added sequentially to a two-necked flask, followed by nitrogen protection, stirring at 0 ℃ under reflux for 12 hours, cooling, washing with anhydrous sodium sulfite solution (3X 50mL), liquid separation, collection of the organic phase, drying with anhydrous sodium sulfate, filtration to concentrate the organic phase, and isolation of the compound by silica gel column using petroleum ether as a developing solvent gave intermediate B13. LC-MS: measurement value: 320.10([ M + H)] + ) The theoretical value is as follows: 319.00.
preparation of intermediate B14:
the intermediate B13(10.0mmol), the raw material A9(10.0mmol) and Pd were sequentially added to a two-necked flask 2 (dba) 3 Catalyst 0.1mmol, potassium tert-butoxide (20mmol), tri-tert-butylphosphine (0.3mmol), toluene 50mL, under nitrogen, stirred at 110 ℃ under reflux for 4.5 h, filtered after cooling and concentrated the organic phase, purified by column chromatography on silica gel with petroleum ether: ethyl acetate 10:1 as developing solvent to afford intermediate B14 in 62.19% yield. LC-MS: measurement value: 401.10([ M + H)] + ) The theoretical value is as follows: 400.05.
preparation of intermediate B15:
sequentially adding the intermediate B14(5.0mmol) and N, N-dimethylformamide into a two-neck bottle(DMAc)50mL, palladium acetate (0.5mmol), potassium carbonate (25.0mmol), tetra-n-butylammonium bromide (2.5mmol) and triphenylphosphine (5mmol) were heated under reflux and stirred for 20 hours, the reaction mixture was concentrated by filtration, and the compound was isolated by means of a silica gel column using petroleum ether as a developing solvent to give intermediate B15. LC-MS: measurement value: 365.18([ M + H)] + ) The theoretical value is as follows: 364.08.
preparation of intermediate B16:
synthesis of intermediate B16 reference intermediate B10, except intermediate B15 was used instead of intermediate B9 to give intermediate B16. LC-MS: measurement value: 330.32([ M + H)] + ) The theoretical value is as follows: 329.38.
preparation of intermediate C7:
synthesis of intermediate C7 reference intermediate C2, except intermediate B17 was used instead of intermediate B2 to afford intermediate C7. LC-MS: measurement value: 864.05([ M + H)] + ) The theoretical value is as follows: 863.12.
preparation of compound 281:
preparation of compound 281 reference compound 129 except intermediate C7 was used instead of intermediate C2 to give compound 281. LC-MS: measurement value: 879.55([ M + H)] + ) The theoretical value is as follows: 878.69.
example 8 synthesis of compound 231:
preparation of intermediate B18:
to a three-necked flask, the starting material A10(10mmol), 50mL anhydrous DMF was added sequentially, and Cs was added using nitrogen blanket 2 CO 3 (20mmol), A11(10mmol), the mixture was heated with stirring for 24 h. After the reaction, 100mL of water was added to quench the reaction, and a large amount of white precipitate was filtered off. The precipitate was collected and dried over anhydrous sodium sulfate, filtered, and concentrated to a solid, and passed through a silica gel column using petroleum ether: purification with 500:1 developing solvent afforded intermediate B18. LC-MS: measurement value: 608.21([ M + H)] + ) The theoretical value is as follows: 607.19.
preparation of intermediate C8:
synthesis of intermediate C8 reference intermediate C2, except intermediate B18 was used instead of intermediate B2 to afford intermediate C8. LC-MS: measurement value: 780.82([ M + H)] + ) The theoretical value is as follows: 779.79.
preparation of compound 231:
preparation of Compound 231 reference Compound 129, except intermediate C8 was used instead of intermediate C2, to afford Compound 23
1. LC-MS: measurement value: 796.42([ M + H)] + ) The theoretical value is as follows: 795.37.
example 9 synthesis of compound 234:
preparation of intermediate B19:
synthesis of intermediate B19 reference was made to intermediate B18, except starting material a13 was used instead of starting material a11 to afford intermediate B19. LC-MS: measurement value: 567.31([ M + H)] + ) The theoretical value is as follows: 566.29.
preparation of intermediate C9:
synthesis of intermediate C9 reference intermediate C2, except intermediate B19 was used instead of intermediate B2 to afford intermediate C9. LC-MS: measurement value: 739.92([ M + H)] + ) The theoretical value is as follows: 738.89.
preparation of compound 234:
preparation of compound 234 compound 129 was referenced except intermediate C9 was used instead of intermediate C2 to afford compound 234. LC-MS: measurement value: 755.41([ M + H)] + ) The theoretical value is as follows: 754.46.
example 10 synthesis of compound 300:
preparation of intermediate C11:
synthetic reference for intermediate C10Intermediate C2, except starting material a15 was used in place of starting material a7 to give intermediate C11. LC-MS: measurement value: 1194.45([ M + H)] + ) The theoretical value is as follows: 1193.59.
preparation of compound 300:
preparation of compound 300 reference compound 129 was prepared except intermediate C11 was used instead of intermediate C2 to afford compound 300. LC-MS: measurement value: 1210.26([ M + H)] + ) The theoretical value is as follows: 1209.17.
example 11 synthesis of compound 308:
preparation of intermediate C10:
synthesis of intermediate C10 reference intermediate C2, except starting material a16 was used instead of starting material a7 to afford intermediate C10. LC-MS: measurement value: 1044.26([ M + H)] + ) The theoretical value is as follows: 1043.36.
preparation of compound 308:
preparation of compound 308 reference compound 129 was prepared except intermediate C10 was used instead of intermediate C2 to afford compound 308. LC-MS: measurement value: 1059.87([ M + H)] + ) The theoretical value is as follows: 1058.94.
example 12 synthesis of compound 179:
preparation of compound 179:
Example 13 synthesis of compound 2:
preparation of intermediate B20:
adding raw material A17(2mmol) into a dry three-neck flask, adding 20mL of dry ether, then slowly adding boron tribromide (2mmol) dropwise at-10 ℃, slowly returning to room temperature, reacting for 18 hours, and draining the solvent to obtain intermediate B20. LC-MS: measurement value: 243.91([ M + H)] + ) The theoretical value is as follows: 242.91.
preparation of intermediate B21:
synthesis of intermediate B21 reference intermediate B2, except that carbazole was used instead of 3, 6-di-tert-butylcarbazole, giving intermediate B21. LC-MS: measurement value: 527.89([ M + H)] + ) The theoretical value is as follows: 526.99.
preparation of intermediate B22:
intermediate B21(5mmol) was added to a dry three-necked flask, diethyl ether 30mL was added, cooled to-78 deg.C, n-butyllithium (5mmol) was slowly added dropwise, followed by reaction at-78 deg.C for 1 hour, intermediate 20(6mmol) was added to the reaction mixture, and the reaction was allowed to warm slowly to room temperature for 24 hours. After the reaction, two drops of methanol were added, and extracted with a dichloromethane solution, dried over anhydrous sodium sulfate and filtered, and then the reaction solution was concentrated and passed through a silica gel column using petroleum ether: purification with 500:1 developing solvent gave compound intermediate 22. LC-MS: measurement value: 564.10([ M + H)] + ) The theoretical value is as follows: 563.09.
preparation of intermediate C12:
synthesis of intermediate C12 reference intermediate C2, except intermediate B22 was used instead of intermediate B2 to afford intermediate C12. LC-MS: measurement value: 736.56([ M + H)] + ) The theoretical value is as follows: 735.69.
preparation of compound 2:
preparation of compound 2 reference compound 129 was prepared except intermediate C12 was used instead of intermediate C2 to afford compound 2. LC-MS: measuringSetting the value: 752.34([ M + H)] + ) The theoretical value is as follows: 751.27.
example 14 synthesis of compound 74:
preparation of intermediate B23:
adding raw material A18(2mmol) into a dry three-neck flask, adding 20mL of dry ether, then slowly adding boron tribromide (2mmol) dropwise at-10 ℃, slowly returning to room temperature, reacting for 18 hours, and draining the solvent to obtain intermediate B23. LC-MS: measurement value: 245.97([ M + H)] + ) The theoretical value is as follows: 244.91.
preparation of intermediate B24:
synthesis of intermediate B24 reference is made to intermediate B21, except that diphenylamine is used in place of carbazole to afford intermediate B24. LC-MS: measurement value: 566.11([ M + H ]] + ) The theoretical value is as follows: 565.11.
preparation of intermediate C13:
synthesis of intermediate C13 reference intermediate C2, except intermediate B24 was used instead of intermediate B2 to afford intermediate C13. LC-MS: measurement value: 738.76([ M + H)] + ) The theoretical value is as follows: 737.71.
preparation of compound 74:
preparation of compound 74 compound 129 was referenced to compound 129 except intermediate C13 was used instead of intermediate C2 to afford compound 74. LC-MS: measurement value: 754.34([ M + H)] + ) The theoretical value is as follows: 753.27.
example 15 synthesis of compound 228:
preparation of intermediate B23:
adding raw material A19(2mmol) into a dry pressure-resistant bottle, adding 10mL of dry toluene, slowly adding boron tribromide (2mmol) dropwise at-10 ℃, slowly heating to 120 ℃, reacting for 18 hours, and mixingThe solvent was then dried by suction to afford intermediate B23. LC-MS: measurement value: 334.56([ M + H)] + ) The theoretical value is as follows: 333.62.
preparation of intermediate B24:
intermediate B21(5mmol) was charged in a dry three-necked flask, dried toluene 30mL was added, cooled to-78 deg.C, n-butyllithium (5mmol) was slowly added dropwise, and the mixture was reacted at-78 deg.C for 1 hour, and the reaction mixture and starting material A20(2.6mmol) were slowly added dropwise to a toluene solution of intermediate B23(6mmol) while slowly warming to room temperature and reacting for 24 hours. After the reaction, two drops of methanol were added, and extracted with a dichloromethane solution, dried over anhydrous sodium sulfate and filtered, and then the reaction solution was concentrated and passed through a silica gel column using petroleum ether: purification with 500:1 developing solvent gave compound intermediate 24. LC-MS: measurement value: 694.10([ M + H)] + ) The theoretical value is as follows: 693.09.
preparation of intermediate C14:
synthesis of intermediate C14 reference intermediate C2, except intermediate B24 was used instead of intermediate B2 to afford intermediate C14. LC-MS: measurement value: 866.56([ M + H)] + ) The theoretical value is as follows: 865.69.
preparation of compound 228:
preparation of compound 228 reference compound 129 was prepared except intermediate C14 was used instead of intermediate C2 to afford compound 224. LC-MS: measurement value: 892.34([ M + H)] + ) The theoretical value is as follows: 881.27.
the following representative compounds were also prepared according to the above synthetic method and are characterized by the structures shown in table 1 below.
Table 1:
the compound can be used as a doping material of a light-emitting layer in a light-emitting device. The physicochemical properties of the compounds prepared according to the invention in the above examples were tested, note that: PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured in the thin film state by Fluorolog-3 series fluorescence spectrometer from Horiba. The results are shown in table 2 below:
table 2:
as can be seen from the data in the table 2, the compound has higher fluorescence quantum efficiency as a doping material, and is beneficial to improving the luminous efficiency of a device; meanwhile, the spectrum FWHM of the material is narrow, so that the color purity of the device can be effectively improved.
The technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may be divided into a plurality of regions, for example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), or zinc oxide (ZnO), or any combination thereof can be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives, and the like.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The preparation process of the organic electroluminescent device is described as follows with reference to the attached figure 2: an anode 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. In the preparation of the organic light-emitting layer 4, the organic light-emitting layer 4 is formed by a co-deposition method using a wide band gap material source, an electron donor material source, an electron acceptor material source, and a resonance TADF material source.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
2. placing the glass plate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, forming a hole injection layer by vacuum evaporation of a hole injection material on the anode layer film at a rate of0.1-0.5nm/s；
3. Vacuum evaporating hole transport material on the hole injection layer to form a hole transport layer with an evaporation rate of 0.1-0.5nm/s,
4. vacuum evaporating an electron blocking layer on the hole transport layer, wherein the evaporation rate is 0.1-0.5 nm/s;
5. the organic light-emitting layer of the device is vacuum evaporated on the electron barrier layer, the organic light-emitting layer material comprises a main material and TADF dye, and the evaporation rate of the main material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by a multi-source co-evaporation method to enable the dye to reach a preset doping proportion;
6. vacuum evaporating a hole blocking layer on the organic light-emitting layer, wherein the evaporation rate is 0.1-0.5 nm/s;
7. forming an electron transport layer on the hole blocking layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5 nm/s;
8. LiF is evaporated on the electron transport layer in vacuum at a speed of 0.1-0.5nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at a speed of 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
Device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％4(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, the total thickness is generally 5-30nm, and the thickness is 10nm in the embodiment; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, 40nm in this embodiment; host is a main body material with wide band gap of an organic light-emitting layer, the compound 4 of the invention is a dye with the doping concentration of 2 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
A DC voltage was applied to the organic electroluminescent element D1 prepared in this example, and 10cd/m was measured 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 480nm, a half-peak width of 27nm, CIE color coordinates (x, y) (0.16,0.27), and external quantum efficiency EQE of 36.0% was obtained. The electroluminescence spectrum is shown in FIG. 1.
Device example 2
The same preparation method as that of device example 1 was followed except that the dye used in the light-emitting layer was replaced with 129 from 4, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％129(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D2 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 485nm, a half-peak width of 33nm, CIE color coordinates (x, y) ═ 0.11,0.32, and external quantum efficiency EQE of 33.4% was obtained.
Device example 3
The same procedure as in device example 1 was conducted except that the dye used in the light-emitting layer was replaced with 110 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％110(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D3 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were obtained by setting the CIE color coordinates (x, y) to (0.18, 0) with a wavelength of 490nm, a half-width of 26 nm.33) And a sky blue emission (driving voltage of 2.5V) with an external quantum efficiency EQE of 32.9%.
Device example 4
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced with 113 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％113(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D4 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 In the characteristics in light emission, sky blue emission (driving voltage of 2.6V) having a wavelength of 502nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) ═ 0.27,0.42, and an external quantum efficiency EQE of 36.4% was obtained.
Device example 5
The same as the preparation method of device example 1 except that the dye in the light-emitting layer was replaced from 4 to 195. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％195(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D5 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.6V) having a wavelength of 490nm, a half-peak width of 25nm, CIE color coordinates (x, y) ═ 0.11,0.29, and an external quantum efficiency EQE of 33.4% was obtained.
Device example 6
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced from 4 to 272. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％272(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D6 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were found to have a wavelength of 492nm, a half-width of 32nm, CIE color coordinates (x, y) ((0.20, 0.47)), and an outer colorSky blue light emission (driving voltage of 2.8V) with a quantum efficiency EQE of 34.0%.
Device example 7
The same as the production method of device example 1 except that the dye in the light-emitting layer was replaced from 4 to 281. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％281(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D7 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.6V) having a wavelength of 487nm, a half-peak width of 29nm, CIE color coordinates (x, y) ═ 0.17,0.33, and an external quantum efficiency EQE of 30.5% was obtained.
Device example 8
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced with 231 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％231(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D8 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.5V) having a wavelength of 493nm, a half-peak width of 27nm, CIE color coordinates (x, y) ═ 0.148,0.33, and an external quantum efficiency EQE of 31.1% was obtained.
Device example 9
The same as the production method of device example 1 except that the dye in the light-emitting layer was replaced with 234 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％234(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D9 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were determined to have a wavelength of 495nm, a half-width of 29nm, CIE color coordinates (x, y) ═ 0.23,0.44, and an external quantum efficiency EQE of33.6% of sky blue light emission (driving voltage of 2.6V).
Device example 10
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 300 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％300(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D10 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.7V) having a wavelength of 500nm, a half-peak width of 29nm, CIE color coordinates (x, y) (0.29,0.39), and an external quantum efficiency EQE of 33.4% was obtained.
Device example 11
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with 4 to 308. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％308(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D11 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.7V) having a wavelength of 516nm, a half-peak width of 29nm, CIE color coordinates (x, y) ═ 0.27,0.48, and an external quantum efficiency EQE of 34.2% was obtained.
Device example 12
The same procedure as in device example 1 was followed except that 179 was used instead of 4 for the dye used in the light-emitting layer. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％179(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D12 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were found to have a wavelength of 499nm, a half-width of 28nm, CIE color coordinates (x, y) ═ 0.15,0.36, and an external quantum efficiency EQE of 315% of sky blue emission (drive voltage of 2.6V).
Device example 13
The same procedure as in device example 1 was conducted except that the dye in the light-emitting layer was replaced with 9 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％9(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D13 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 486nm, a half-peak width of 30nm, CIE color coordinates (x, y) (0.17,0.33), and external quantum efficiency EQE of 30.2% was obtained.
Device example 14
The same procedure as in device example 1 was conducted except that the dye used in the light-emitting layer was replaced with 14 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％14(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D14 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 493nm, a half-peak width of 30nm, CIE color coordinates (x, y) ═ 0.21,0.36, and an external quantum efficiency EQE of 34.8% was obtained.
Device example 15
The same procedure as in device example 1 was followed except that 29 was used instead of 4 as the dye in the light-emitting layer. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％29(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D15 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were determined to obtain sky blue emission having a wavelength of 499nm, a half-peak width of 25nm, CIE color coordinates (x, y) (0.12,0.39), and an external quantum efficiency EQE of 30.4%Light (drive voltage 2.7V).
Device example 16
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced from 4 to 77. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％77(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D16 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.7V) having a wavelength of 500nm, a half-peak width of 29nm, CIE color coordinates (x, y) ═ 0.19,0.32, and an external quantum efficiency EQE of 33.4% was obtained.
Device example 17
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced with 181 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％181(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D17 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were that yellow light emission (driving voltage 2.6V) having a wavelength of 502nm, a half-width of 29nm, CIE color coordinates (x, y) ═ 0.18,0.38, and an external quantum efficiency EQE of 30.7% was obtained.
Device example 18
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced with 201 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％201(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D18 prepared in this example were as follows: applying a DC voltage, measuring 10cd/m 2 The light emission characteristics were determined to obtain a sky blue emission having a wavelength of 491nm, a half-width of 27nm, CIE color coordinates (x, y) (0.13,0.25), and an external quantum efficiency EQE of 32.7%Light (drive voltage 2.5V).
Device example 19
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 227 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％227(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D19 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The light emission characteristics were that sky blue emission (driving voltage of 2.6V) having a wavelength of 489nm, a half-peak width of 26nm, CIE color coordinates (x, y) (0.28,0.30), and an external quantum efficiency EQE of 33.9% was obtained.
Device example 20
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 229 instead of 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％229(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D20 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 490nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) (0.24,0.28), and external quantum efficiency EQE of 33.9% was obtained.
Device example 21
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 257 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％257(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D21 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 As for the characteristics in light emission, sky blue having a wavelength of 480nm, a half-width of 26nm, CIE color coordinates (x, y) ((0.12, 0.29)) and an external quantum efficiency EQE of 34.0% was obtainedThe color emitted light (driving voltage 2.6V).
Device example 22
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 290 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％290(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D22 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.6V) having a wavelength of 487nm, a half-peak width of 27nm, CIE color coordinates (x, y) ═ 0.23,0.27, and an external quantum efficiency EQE of 31.4% was obtained.
Device example 23
The same as the production method of device example 1 except that the dye used in the light-emitting layer was replaced with 2 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％2(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D23 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 In the characteristics in light emission, sky blue light emission (driving voltage 2.7V) with a wavelength of 469nm, a half-width of 31nm, CIE color coordinates (x, y) ═ 0.23,0.29, and external quantum efficiency EQE of 29.4% was obtained.
Device example 24
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 74 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％74(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D24 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 As for the characteristics in light emission, sky blue having a wavelength of 465nm, a half-width of 31nm, CIE color coordinates (x, y) ((0.23, 0.29)), and an external quantum efficiency EQE of 28.4% was obtainedColor emission (driving voltage of 2.6V).
Device example 25
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with 228 from 4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％228(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D25 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristic in light emission was that sky blue light emission (driving voltage of 2.7V) having a wavelength of 469nm, a half-peak width of 31nm, CIE color coordinates (x, y) ═ 0.23,0.33, and an external quantum efficiency EQE of 30.4% was obtained.
Comparative device example 1
The same preparation method as that of device example 1 was used except that the compound 4 of the present invention used in the light-emitting layer was replaced with the compound P1 in the prior art, and the specific device structure was as follows:
ITO/HI (10nm)/HT (30nm)/EBL (10nm)/Host:2 wt% P1(30nm)/HBL (10nm) ET (30nm)/LiF (0.5nm)/Al (150nm) device performance results of the organic electroluminescent device DD1 prepared in this example were as follows: when a dc voltage was applied and the characteristics of 10cd/m2 light emission were measured, blue light emission (driving voltage of 3.6V) having a wavelength of 469nm, a peak width at half maximum of 27nm, CIE color coordinates (x, y) of (0.12,0.18), and an external quantum efficiency EQE of 29.3% was obtained.
Comparative device example 2
The same preparation method as that of device example 2 except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P2 of the prior art, and a specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:2wt％P2(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device DD2 prepared in this example are as follows: applying a DC voltage, and measuring 10cd/m 2 The characteristics in light emission were determined by obtaining a 466nm wavelength, a 30nm half-width, and CIE color coordinates (x, y) ═ 0.13,0.16) and an external quantum efficiency EQE of 18.4% (driving voltage of 3.3V).
The structural formulas of the various organic materials used in the above examples are as follows:
specific performance data of the organic electroluminescent devices D1 to D25 and the devices DD1 and DD2 prepared in the above respective device examples are detailed in table 3 below.
Table 3:
the experimental data show that the compound greatly simplifies the introduction process of B by introducing a B-N polar covalent bond into B, N molecular skeleton with multiple resonance effect (MR), and simultaneously reserves the MR effect when B, N is in contraposition, thereby expanding a narrow-band emission molecular skeleton system. Compared with the comparative examples 1 and 2, the luminescent material of the series of materials has the advantages of simpler and more efficient synthesis, reaction yield of more than 90 percent, high brightness, greatly enriched multiple resonance-thermal activation delayed fluorescence material system and good application prospect, and the full width at half maximum (FWHM) of a molecular fluorescence spectrum is only 26-32nm, and PLQY is more than 90 percent. It is emphasized that the compounds of the present invention, in comparison with comparative example 2, in which a substituent, which may be an alkyl substituent or an aryl substituent, is retained at the para position of the benzene ring in the center of the skeleton attached to the nitrogen atom, allow for a higher selectivity of the reaction and a high yield of the product with boron, whereas without the substituent the reaction can only produce a product with boron on one side.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims. It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A luminescent material represented by the following formula (1):
in the formula (1), the dotted line represents connection or non-connection;
y represents N or B;
ring A, ring B, ring C, ring D, ring E and ring F each independently represent one of an aromatic ring of C6-C20 and a heteroaromatic ring of C5-C20;
n1, n2, n3 are each independently 0 or 1;
X 1 、X 2 and X 3 Each independently selected from the group consisting of a single bond and CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O or S (O) O, S, C 2 ；
The R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from one of the following substituted or unsubstituted groups: chain alkyl of C1-C36, cycloalkyl of C3-C36, arylamino of C6-C30, heteroarylamino of C3-C30, C6-A monocyclic aryl group of C60, a fused ring aryl group of C6-C60, an aryloxy group of C6-C60, a monocyclic heteroaryl group of C5-C60, or a fused ring heteroaryl group of C5-C60;
R a 、R b 、R c 、R d 、R e 、R f and R g Each independently represents a single substituent up to the maximum allowed number of substituent groups and each is independently selected from hydrogen, deuterium, halogen or one of the following substituted or unsubstituted groups: one of chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitryl, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and monoheteroaryl of C5-C60; r g Selected from arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and heteroaryl of C5-C60;
the R is a 、R b 、R c 、R d 、R e 、R f And R g May be connected to each other by a single bond or may be fused to each other to form a ring;
when the above R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R a 、R b 、R c 、R d 、R e And R f When the substituent exists, the substituent groups are respectively and independently selected from any one of deuterium, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroaryl of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 and fused ring heteroaryl of C5-C60.
2. The light-emitting material according to claim 1, having a structure represented by any one of the following formulae (2), (3), (4), (5), (6), and (7):
in the formulae (2), (3), (4), (5), (6) and (7), X is 1 、X 2 、X 3 、n1、n2、n3、R a 、R b 、R c 、R d 、R e 、R f And R g Are the same as defined in formula (1).
3. The luminescent material according to claim 2, wherein X is represented by formula (2), formula (3), formula (4), formula (5), formula (6) or formula (7) 2 Is a single bond, n2 is 0 or 1;
or, the X 1 、X 2 And X 3 Are respectively a single bond at the same time;
or, when X 1 And X 3 When it is simultaneously a single bond, X 2 Is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 、O、S；
Or, when X 1 And X 3 At the same time being CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 And O, S, X 2 Is BR 4 。
4. The luminescent material according to claim 1, having a structure represented by the following formula (8) or formula (9):
in the formulae (8) and (9), the dotted line represents a connection or non-connection; x 1 、X 2 、X 3 、n1、n2、n3、R a 、R c 、R d 、R e 、R f And R g Are all as defined in formula (1);
preferably, in formula (8) or formula (9), the dotted line represents a link;
preferably, in the formulae (8) and (9), X is 2 Is a single bond, n2 is 0 or 1; or, the X 1 、X 2 And X 3 Are respectively a single bond at the same time; or, when X 1 And X 3 While being a single bond, X 2 Is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 O, S; or, when X 1 And X 3 At the same time is CR 1 R 2 、NR 3 、BR 4 、SiR 5 R 6 And O, S, X 2 Is BR 4 。
5. The luminescent material according to any one of claims 1,2 or 4,
the ring A, the ring B, the ring C, the ring D, the ring E and the ring F respectively and independently represent any one of aromatic rings of C6-C10 and heteroaromatic rings of C5-C10;
preferably, the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from one of a benzene ring and a naphthalene ring;
or preferably, the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from one of a benzene ring, a naphthalene ring or a pyridine ring.
6. The luminescent material according to any one of claims 1 to 5, wherein R is a 、R b 、R c 、R d 、R e 、R f And R g Each independently selected from one of hydrogen, deuterium, halogen, chain alkyl of C1-C6, cycloalkyl of C3-C6, alkoxy of C1-C6, thioalkoxy of C1-C6, cyano, arylamino of C6-C20, heteroarylamino of C3-C20, aryl of C6-C30, aryloxy of C6-C30 and heteroaryl of C5-C30; the R is a 、R b 、R c 、R d 、R e 、R f And R g May be connected to each other by a single bond or may be fused to form a ring;
preferably, said R is a 、R b 、R c 、R d 、R e 、R f Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, camphyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydronaphthyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, furanyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, 2,2, 2-trifluoroethyl, phenyl, phenanthryl, and a phenanthryl, Benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidyl, benzopyrimidinyl, quinoxalinyl, benzoxazolyl, phenanthrolinyl, and phenanthrolinyl, 1, 5-diazanthryl group, 2, 7-diazpyrenyl group, 2, 3-diazpyrenyl group, 1, 6-diazpyrenyl group, 1, 8-diazpyrenyl group, 4, 5-diazenyl group, 4,5,9, 10-tetraazaperylenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinylOne of a group, a purine group, a pteridine group, an indolizine group, a benzothiadiazolyl group, a9, 9-dimethylazlidine group, a triarylamine group, adamantane, a fluorophenyl group, a methylphenyl group, a trimethylphenyl group, a cyanophenyl group, a tetrahydropyrrole, piperidine, a methoxy group and a silicon group, or a combination of two substituent groups;
still more preferably, said R a 、R b 、R c 、R d 、R e 、R f Each independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazahrenyl, 2, 7-diazapyl, 2, 3-diazapyl, 1, 6-diazapyl, 1, 8-diazapyl, 4, 5-diazapyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocaineyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 3-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, indolizinyl, benzothiadiazolyl, 9-dimethylazinylTriarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy or silyl groups.
7. The luminescent material according to any one of claims 1 to 6, wherein R is g Selected from phenyl, naphthyl, anthryl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, n-hexyl, cyclohexyl, neohexyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, 1, 5-diazoanthrenyl, 2, 7-diazapyl, 2, 3-diazapyl, 1, 6-diazapyl, 1, 8-diazapyl, 4, 5-diazapyl, 4,5,9, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinylOne of a group, a1, 2, 3-triazinyl group, a tetrazolyl group, a1, 2,4, 5-tetrazinyl group, a1, 2,3, 4-tetrazinyl group, a1, 2,3, 5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a benzothiadiazolyl group, a9, 9-dimethylazinyl group, a triarylamino group, an adamantane, a fluorophenyl group, a methylphenyl group, a trimethylphenyl group, a cyanophenyl group, a tetrahydropyrrole, a piperidine group, a methoxy group and a silicon group.
8. The luminescent material according to claim 1, wherein the compound is selected from the following compounds of specific structures:
9. use of the luminescent material according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the luminescent material is applied as a luminescent layer material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one light-emitting material according to any one of claims 1 to 9;
preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the light-emitting material according to any one of claims 1 to 9.
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| US20210202861A1 (en) * | 2019-12-26 | 2021-07-01 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| WO2021214306A1 (en) * | 2020-04-23 | 2021-10-28 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| JP2022088252A (en) * | 2020-12-02 | 2022-06-14 | 出光興産株式会社 | Compound and organic electroluminescent device |
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| US20210202861A1 (en) * | 2019-12-26 | 2021-07-01 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| WO2021214306A1 (en) * | 2020-04-23 | 2021-10-28 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| JP2022088252A (en) * | 2020-12-02 | 2022-06-14 | 出光興産株式会社 | Compound and organic electroluminescent device |
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