CN110698387A - Fused ring compound and preparation method and application thereof - Google Patents
Fused ring compound and preparation method and application thereof Download PDFInfo
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- CN110698387A CN110698387A CN201910832675.5A CN201910832675A CN110698387A CN 110698387 A CN110698387 A CN 110698387A CN 201910832675 A CN201910832675 A CN 201910832675A CN 110698387 A CN110698387 A CN 110698387A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 181
- 238000002360 preparation method Methods 0.000 title claims abstract description 39
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 133
- 239000000463 material Substances 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 48
- 230000008569 process Effects 0.000 claims abstract description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 131
- 239000010410 layer Substances 0.000 claims description 86
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 45
- -1 cyano, hydroxyl Chemical group 0.000 claims description 45
- 229910052805 deuterium Inorganic materials 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 239000002994 raw material Substances 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 150000007857 hydrazones Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000004982 aromatic amines Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 239000000758 substrate Substances 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
- LVSJLTMERPMMEE-UHFFFAOYSA-N 1-amino-1-[cyano(nitro)amino]guanidine Chemical compound C(#N)N(N(C(N)=N)N)[N+](=O)[O-] LVSJLTMERPMMEE-UHFFFAOYSA-N 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
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- 229910052796 boron Inorganic materials 0.000 claims description 3
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
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- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
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- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
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- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
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- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 2
- MWPCBCGAQVXDCZ-UHFFFAOYSA-N 1-amino-1-nitramidoguanidine Chemical compound [N+](=O)([O-])NN(C(N)=N)N MWPCBCGAQVXDCZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
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- 238000010168 coupling process Methods 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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Abstract
The invention discloses a fused ring compound and a preparation method and application thereof. The fused ring compound has a structure shown as a formula (I) or a formula (II). The HOMO energy level and the LUMO energy level of the condensed ring compound are completely separated, so that the triplet state energy level is improved while the energy gap width of the material is reduced, and the light-emitting efficiency is prevented from being reduced due to energy backflow from an object material to a host material; HOMO and LUMO energy levels are matched with adjacent materials, and the driving voltage is small; the molecular structure of the material is large in size, and the intramolecular conjugation property is good, so that the material has good thermal stability, the material can be prevented from being heated and decomposed in the process of film formation or use, the loss of the function of a material layer is avoided, and the luminous efficiency and the luminous performance of a device are improved. The invention also provides a preparation method of the fused ring compound and application of the fused ring compound as an organic electroluminescent material.
Description
Technical Field
The invention relates to the technical field of display, in particular to a fused ring compound and a preparation method and application thereof.
Background
In 1987, dane cloud doctor in the laboratory of Kodak corporation of america (Eastman Kodak) first made the first organic light-emitting diode (OLED) device by vacuum evaporation, and used transparent and conductive Indium Tin Oxide (ITO) as the anode, and evaporated diamine derivative and tris (8-hydroxyquinoline) aluminum on the anode in sequence, and used magnesium-silver alloy as the cathode material, and this multilayer structure can reduce the driving voltage of the OLED device, and effectively improve the charge injection problem between the material molecules and the electrode interface, and the device performance and lifetime are also improved accordingly.
Compared with an inorganic electroluminescent device (ELD), the OLED device has many advantages of low driving voltage, high luminous efficiency, high contrast, high color saturation, wide viewing angle, fast response time, and the like. In the prior art, an OLED device generally includes a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and is matched with appropriate electrodes, and each of the layers is respectively composed of the following materials: hole injection materials, hole transport materials, light emitting materials, hole blocking materials, electron transport materials, electron injection materials. The OLED light-emitting layer manufactured by adopting a doping mode has advantages in the light-emitting efficiency of the device, so that the light-emitting layer material is usually formed by doping a host material with a guest material, and the host material is an important factor influencing the light-emitting efficiency and the performance of the OLED device. 4,4' -Bis (9H-carbazol-9-yl) biphenol (CBP) is a widely used host material for a light-emitting layer, and has good hole transport properties, but when CBP is used as a host material, the CBP has a low glass transition temperature and is easily recrystallized, so that the service performance and the light-emitting efficiency of an OLED device are reduced, and in addition, CBP is a hole-type host material, the transport of electrons and holes is not balanced, the recombination efficiency of excitons is low, and a light-emitting region is not ideal, and the roll-off phenomenon of the OLED device is severe during operation, so that the efficiency of energy transfer from the host material to a guest material is low, and further, the device efficiency is reduced.
Disclosure of Invention
Therefore, the technical problem to be solved by the present invention is to overcome the defects of low stability of the host material of the light emitting layer, low energy transfer efficiency, low light emitting efficiency of the device, and short service life in the prior art, so as to provide a condensed ring compound, and a preparation method and an application thereof.
In a first aspect, the present invention provides a fused ring compound having a structure represented by formula (I) or formula (II):
R1-R14independently of one another, from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl of (a), substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkylamino group of (A), substituted or unsubstituted C2-C60Substituted or unsubstituted C2-C60Alkynylamino, substituted or unsubstituted C1-C60Alkoxy, substituted or unsubstituted C2-C60Of (a) is an alkylene oxideRadical, substituted or unsubstituted C2-C60Alkynyloxy of, substituted or unsubstituted C1-C60Thioalkoxy, substituted or unsubstituted C2-C60Thioalkenyloxy, substituted or unsubstituted C2-C60With a thioalkynyloxy group, substituted or unsubstituted C1-C60With an alkyl boron group, substituted or unsubstituted C2-C60With an alkene boron group, substituted or unsubstituted C2-C60With a boron alkynyl group, substituted or unsubstituted C1-C60Ester group of (1), substituted or unsubstituted C1-C60Amide group of (A), substituted or unsubstituted C4-C60Aryl, substituted or unsubstituted C3-C60Heteroaryl, substituted or unsubstituted C4-C60Aryloxy group of (1), substituted or unsubstituted C4-C60With an aromatic amine group, substituted or unsubstituted C4-C60Thioaryloxy, substituted or unsubstituted C4-C60An arylboron group of, or
R1-R14Any two to four adjacent groups of which are linked to form one or more groups of rings A,
the ring A is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C60Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring;
Ar1selected from a group P substituted or unsubstituted with one or more substituents selected from:
C4-C60aryl of (C)3-C60Heteroaryl of (A), C4-C60Aryloxy group of (A), C4-C60Aromatic amine group of (2), C4-C60Thioaryloxy of (C)4-C60Aryl boron group of (A), C4-C60Aryl phosphine group of (A), C4-C60Heteroaryloxy of (A), C4-C60Heteroaromatic amino group of (1), C4-C60Thio-heteroaryloxy of (A), C4-C60Heteroaryl boron group of (A), C4-C60The heteroaromatic phosphine group of (1);
the substituents are independently of one another selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4Alkenyl of (a), halogen-substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)2-C12Heteroaryl of (A), C2-C12A heteroaryl amine of (a), halogen-substituted C2-C12Heteroaryl, deuterium substituted C of2-C12The heteroaryl group of (a).
Further, in the above-mentioned fused ring compound,
Ar1is composed of
X1-X5Each independently selected from N or CR15The number of N is 0 to 3,
it is shown that the connecting key is,
R15independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30Substituted or unsubstituted arylamine groups ofC4-C30Thioaryloxy, substituted or unsubstituted C4-C30Arylboron group of (A), substituted or unsubstituted C4-C30An aryl phosphorus group of, or
Two adjacent R15Are connected to form a ring B,
the ring B is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring; or
Ar1Is selected from
Denotes a connecting bond, T1-T2Independently of one another, selected from the group consisting of the connecting bonds O, S, SO2、CO、NR17、C(R17)2、POR17N1 is an integer of 0 to 3, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 4,
R16independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30Arylboron group of (A), substituted or unsubstituted C4-C30An aryl phosphorus group of, or
Two adjacent R16Are connected to form a ring C,
the ring C is selected from substituted orUnsubstituted 3-7 membered carbocyclic ring, substituted or unsubstituted 3-7 membered heterocyclic ring, substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, the heterocycle is a saturated or unsaturated ring,
R17independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30An arylboron group of, or
Two adjacent R17Are connected to form a ring D,
the ring D is selected from a substituted or unsubstituted cyclic 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring; or
Ar1Is composed of
Y is NR18Or CR18Or O or S, NR18The number of (a) is 0 to 3,
it is shown that the connecting key is,
R18independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl, substituted or notSubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30An arylboron group of, or
Two adjacent R18Are connected to form a ring E,
the ring E is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocyclic ring is a saturated or unsaturated ring, and the heterocyclic ring is a saturated or unsaturated ring.
Further, in the above-mentioned fused ring compound,
Ar1selected from the group consisting of19A substituted or unsubstituted group F selected from:
the substituent R19Independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4An alkenyl group of,Halogen substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)2-C12Heteroaryl of (A), C2-C12A heteroaryl amine of (a), halogen-substituted C2-C12Heteroaryl, deuterium substituted C of2-C12The heteroaryl group of (a);
preferably, the substituent R19Independently of one another, from hydrogen, deuterium, halogen, methyl, deuterated methyl, trifluoromethyl, ethyl, propyl, tert-butyl, cyano, vinyl, phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl or grate, benzofuranyl, benzothienyl, carbazolyl,
wherein,
indicating a bond, ＊ indicating a binding site.
Further, in the above-mentioned condensed ring compound, Ar is1Are electron withdrawing groups.
Further, in the above-mentioned fused ring compound,
R1-R14independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4Alkenyl of (a), halogen-substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)2-C12Heteroaryl of (A), C2-C12A heteroaryl amine of (a), halogen-substituted C2-C12Heteroaryl, deuterium substituted C of2-C12The heteroaryl group of (a); or
R1-R14Any two to four adjacent groups of which are linked to form one or more groups of rings A,
the ring A is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C12Aryl or substituted or unsubstituted C3-C12The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring;
preferably, R1-R14Independently of one another, from the group consisting of hydrogen, deuterium, halogen, methyl, ethyl, propyl, n-butyl, tert-butyl, trifluoromethyl, cyano, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, adamantyl, bornyl, triphenylene, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthryl, benzophenanthrenyl, pyrenyl, chrysenyl, tetracenyl, picenyl, perylenyl, pentylphenyl, pentacenyl, rubinyl, coronenyl, ovaphenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, thienyl, furyl, quinolyl, carbazolyl, pyranyl, thiopyranyl, phthalazinyl, phenazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, indolyl, indolocarbazolyl, phenanthridinyl, acridinyl, terphenyl, phenanthridinyl, phenanthrenyl, perimidine, pteridinyl, quinazolinyl, quinoxalinyl, cinnolinyl, phenanthroline, carbolinyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, dinaphthofuranyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiapyrrolyl, benzonaphthothiapyrrolyl, dinaphthothiazolyl, benzimidazolyl, imidazopyridinyl;
further, in the above-mentioned fused ring compound,
R1-R14independently of one another, from hydrogen, deuterium, halogen, methyl, ethyl, propyl, n-butyl, tert-butylButyl, trifluoromethyl, cyano, phenyl, biphenyl, terphenyl, naphthyl;
cyclo A, B, C, D, E is independently selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, adamantyl, bornyl, triphenylene, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, anthryl, benzophenanthrenyl, pyrenyl, chrysenyl, tetracenyl, picenyl, perylenyl, pentylphenyl, pentacenyl, rubinyl, coronenyl, egg phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, thienyl, furyl, quinolyl, carbazolyl, pyranyl, thiopyranyl, phthalazinyl, phenazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, indolyl, indolocarbazolyl, phenanthridinyl, acridinyl, perimidine, pteridinyl, quinazolinyl, quinoxalinyl, phenanthridinyl, cinnolinyl, phenanthroline, carboline, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, dinaphthofuranyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiapyrrolyl, benzonaphthothiapyrrolyl, dinaphthothiapyrrolyl, benzimidazolyl, imidazopyridinyl.
Further, the fused ring compound has a molecular structure represented by any one of the following:
in a second aspect, the present invention provides a process for producing the above-mentioned fused ring compound,
the synthesis steps of the compound shown in the formula (I) are as follows:
taking a compound shown in a formula (A) and a compound shown in a formula (B) as initial raw materials, and carrying out Suzuki coupling reaction to obtain an intermediate 1-A; carrying out coupling reaction on the intermediate 1-A and a compound shown as a formula (C) to obtain an intermediate 2-A; carrying out coupling reaction on the intermediate 2-A and a compound shown as a formula (D) to obtain an intermediate 3-A; carrying out coupling and ring-closing reaction on the intermediate 3-A to obtain an intermediate 4-A; carrying out nitro reduction and ring closure reaction on the intermediate 4-A to obtain an intermediate 5-A; carrying out coupling reaction on the intermediate 5-A and a compound shown as a formula (E) to obtain a compound shown as a formula (I);
the synthetic route of the compound shown in the formula (I) is shown as follows:
the synthesis steps of the compound shown in the formula (II) are as follows:
taking a compound shown in a formula (F) and a compound shown in a formula (G) as initial raw materials, and carrying out Suzuki coupling reaction to obtain an intermediate 1-B; carrying out coupling reaction on the intermediate 1-B and a compound shown as a formula (H) to obtain an intermediate 2-B; carrying out coupling reaction on the intermediate 2-B and a compound shown as a formula (J) to obtain an intermediate 3-B; the intermediate 3-B is subjected to coupling ring-closing reaction to obtain an intermediate 4-B; carrying out nitro reduction and ring closure reaction on the intermediate 4-B to obtain an intermediate 5-B; carrying out coupling reaction on the intermediate 5-B and a compound shown as a formula (K) to obtain a compound shown as a formula (II);
the synthetic route of the compound shown in the formula (II) is shown as follows:
in a third aspect, the present invention provides an electronic device comprising a substrate, a first electrode formed on the substrate, a second electrode, an organic layer disposed between the first electrode and the second electrode, the organic layer comprising the above-described fused ring compound;
the organic layer comprises a luminescent layer, and at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer;
the light-emitting layer includes a host material containing the above-described fused ring compound and a dopant material.
In a fourth aspect, the present invention provides a display device comprising the above electronic device.
In a fifth aspect, the present invention provides a lighting device comprising the above electronic device.
The technical scheme of the invention has the following advantages:
1. the fused ring compound provided by the invention has a structure shown as a formula (I) or a formula (II), and the HOMO energy level of the fused ring compound is distributed in
The LUMO energy level is distributed on Ar on the unit1On the group, the HOMO energy level and the LUMO energy level are completely separated, so that the triplet state energy level is improved while the energy gap width of the material is reduced, and the light-emitting efficiency is prevented from being reduced due to energy backflow from an object material to a host material; the HOMO and LUMO energy levels are matched to adjacent materials and the driving voltage is small.
2. The fused ring compound provided by the invention has larger molecular structure size and better intramolecular conjugation, so that the fused ring compound has better thermal stability, can avoid the material from being heated and decomposed in the process of film formation or use, avoids the loss of the function of a material layer, and improves the luminous efficiency and luminous performance of a device.
3. The fused ring compound provided by the invention has a three-dimensional structure, molecules cannot be stacked, energy transfer caused by molecular stacking can be avoided, generation of high-energy excitons can be avoided, and annihilation caused by the existence of the high-energy excitons can be effectively reduced.
4. The preparation method of the fused ring compound provided by the invention has the advantages of easily obtained starting materials, mild reaction conditions and simple operation steps, and provides a simple and easily-realized preparation method for large-scale production and application of the fused ring compound.
5. The condensed ring compound is used as a luminescent material, has excellent thermal stability, has LOMO and LUMO energy levels which can be matched with adjacent layers, has small driving voltage, can avoid exciton annihilation caused by molecular stacking, and is high in luminescent efficiency and long in service life.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a graph showing the theoretical calculation results of the HOMO level, LOMO level and energy band gap Eg of compound 13 in example 13 of the present invention;
FIG. 2 is a schematic view of the structures of organic electroluminescent devices in examples 27 to 52 of the present invention and comparative example 1.
Description of reference numerals:
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-luminescent layer, 6-electron transport layer, 7-electron injection layer, 8-cathode.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the accompanying drawings, and it should be understood that the described embodiments are some, but not all embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the description of the present invention, it should be noted that the terms "first", "second", and "third" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance.
This invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concept of the invention to those skilled in the art, and the present invention will only be defined by the appended claims. In the drawings, the size and relative sizes of layers and regions may be exaggerated for clarity. It will be understood that when an element such as a layer is referred to as being "formed on" or "disposed on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly formed on" or "directly disposed on" another element, there are no intervening elements present.
Aryl-as used herein, is a non-fused or fused system.
Heteroaryl-as used herein, comprises at least one atom of N, O, S, P, Si, B, which may be one atom or a plurality of different atoms; the ring may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or the like; the ring may be monocyclic, spiro or fused.
Example 1
This example provides a fused ring compound (compound 1) having the structure shown below:
the synthetic route for compound 1 is shown below:
wherein the synthetic route of the intermediate 5-E is shown as follows:
the preparation method of the compound 1 specifically comprises the following steps:
(1) synthesis of intermediates 1-E:
taking a 500 ml double-neck round-bottom flask, putting a stirrer and an upper connecting reflux pipe into the flask, drying the flask, and filling nitrogen into the flask; the compounds o-nitrobenzoic acid (16.70 g, 1 eq.), o-bromoiodobenzene (28.19 g, 1.0 eq.), and potassium carbonate (K) were added separately2CO31.5 equivalents), ethanol (50 ml), water (50 ml), toluene (200 ml), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.05 eq), then heated to reflux and reacted for 12 hours, and cooled to room temperature after the reaction is completed; quenched by addition of 200 ml of water and extracted with dichloromethane (3 × 400 ml); adding magnesium sulfate into the obtained extract liquid in sequence, drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to afford intermediates 1-E (17.45 g, 63% yield).
(2) Synthesis of intermediates 2-E:
taking a 500 ml double-neck round-bottom flask, putting a stirrer and an upper connecting reflux pipe into the flask, drying the flask, and filling nitrogen into the flask; intermediates 1-E (27.70 g, 1 eq.), bisphenonal diboron (25.41 g, 1 eq.), potassium acetate (Potasilacetate, 19.61 g, 2 eq), (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) (Pd (dppf) Cl, were added separately20.025 eq), 1, 4-dioxane (200 ml), at 120 ℃ for 8 hours; after completion of the reaction, it was cooled to room temperature, quenched with water, extracted with dichloromethane (200 ml. times.3), the extract was dried over anhydrous magnesium sulfate, spun-dried, and the crude product was isolated by silica gel column chromatography to give intermediate 2-E (19.84 g, 61% yield).
(3) Synthesis of intermediate 3-E:
a500 ml two-necked round bottom flask was taken and placed with a stirrer and an upper reflux tube, dried and charged with nitrogen, and then the intermediates 2-E (24.31 g, 1 eq.), 1, 8-dibromonaphthalene (28.59 g, 1 eq.) and potassium carbonate (K) were added separately2CO31.5 eq), ethanol (25 ml), water (25 ml), toluene (100 ml), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.05 eq), the mixture was refluxed for 12 hours; cooling to room temperature after reaction, adding water into a reaction system, extracting by dichloromethane, sequentially adding magnesium sulfate into the obtained extract, drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/hexane)Alkane, 1/10) to yield intermediate 3-E (23.37 g, 58% yield).
(4) Synthesis of intermediates 4-E:
a500 ml two-necked round-bottomed flask was taken, and a stirrer and an upper reflux tube were placed in the flask, followed by drying, nitrogen gas introduction, and addition of the intermediate 3-E (40.30 g, 1 eq.) and dichloro-bis (tricyclohexylphosphine) palladium (PdCl) respectively2(PCy3)23.69 g, 0.05 eq), pivalic acid (t-BuCO)2H, 2 equivalents), cesium carbonate (Cs)2CO32 eq), dimethylacetamide (200 ml), stirred at 120 ℃ for 10 hours; after completion of the reaction, it was cooled to room temperature, the reaction was concentrated, and the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to afford intermediate 4-E (25.44 g, 52% yield).
(5) Synthesis of intermediate 5-E:
a500 ml two-necked round-bottomed flask was taken and charged with a stirrer and an upper reflux tube, dried and charged with nitrogen, and first 4-E (32.31 g, 1 eq.) and triethyl phosphite (P (OEt)31 eq), 1, 2-dichlorobenzene (100 ml), followed by heating at 180 ℃ for 12 hours; after completion of the reaction, it was cooled to room temperature, the reaction was concentrated, and the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to give intermediate 5-E (20.67 g, 71% yield).
(6) Synthesis of Compound 1:
a500 ml two-necked round-bottomed flask was taken, and a stirrer and an upper reflux tube were placed in the flask, followed by drying, nitrogen gas introduction, and addition of intermediate 5-E (29.11 g, 1 eq), Compound I-1(37.50 g, 1 eq), Cesium carbonate (3 eq), and Tris (dibenzylideneacetone) dipalladium (Pd) respectively2(dba)30.05 equivalent), 2-dicyclohexylphosphonium-2 ', 4', 6 ' -triisopropylbiphenyl (xphos, 42.32 g, 0.05 equivalent), then toluene was added and the mixture was refluxed for 24 hours; cooling to room temperature after reaction, filtering the reaction system and concentrating; the crude product was purified by chromatography (ethyl acetate/hexane, 1/10), compound 1(41.62 g, 71% yield).
Elemental analysis: c42H26N4Theoretical value: c, 85.98; h, 4.47; n, 9.55; measured value: c, 85.95; h, performing a chemical reaction on the mixture of the hydrogen peroxide and the nitrogen peroxide,4.49；N，9.56；HRMS(ESI)m/z(M+): theoretical value: 586.2157, respectively; measured value: 586.2164.
example 2
This example provides a fused ring compound (compound 2) having a structure represented by the following formula:
the synthetic route for compound 2 is shown below:
wherein the synthetic route of the intermediate 5-E' is shown as follows:
the preparation method of the compound 2 specifically comprises the following steps:
(1) synthesis of intermediate 1-E':
the difference of the synthesis method of the intermediate 1-E is that 1-bromo-8 iodonaphthalene (31.89 g, 1 equivalent) is used for replacing o-bromoiodobenzene, the proportion of the raw materials is adjusted to obtain the intermediate 1-E' (22.56 g, 69% of yield)
(2) Synthesis of intermediate 2-E':
the same synthesis method as that of intermediate 2-E was used, except that intermediate 1-E (32.70 g, 1 eq.) was used instead of intermediate 1-E, and the proportions of the respective starting materials were adjusted to give intermediate 2-E' (24.39 g, 65% yield).
(3) Synthesis of intermediate 3-E':
the difference from the synthesis of intermediate 3-E is that intermediate 2-E '(29.31 g, 1 eq) was used instead of intermediate 2-E, o-dibromobenzene (23.59 g, 1 eq) was used instead of 1, 8-dibromonaphthalene, and the proportions of the starting materials were adjusted to give intermediate 3-E' (22.17 g, 55% yield).
(4) Synthesis of intermediate 4-E':
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-E ' was replaced with intermediate 3-E ' (40.30 g, 1 eq.) and the proportions of the starting materials were adjusted to give intermediate 4-E ' (16.16 g, 50% yield).
(5) Synthesis of intermediate 5-E':
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-E ' was replaced with intermediate 4-E ' (32.31 g, 1 eq), and the proportions of the starting materials were adjusted to give intermediate 5-E ' (21.83 g, 75% yield).
(6) Synthesis of Compound 2:
the same procedure as for the synthesis of compound 1, except that intermediate 5-E was replaced with intermediate 5-E' (29.11 g, 1 eq), and the proportions of the starting materials were adjusted to give compound 2(41.03 g, 70% yield).
Elemental analysis: c42H26N4Theoretical value: c, 85.98; h, 4.47; n, 9.55; measured value: c, 85.95; h, 4.47; n, 9.58; HRMS (ESI) M/z (M)+): theoretical value: 586.2157, respectively; measured value: 586.2155.
example 3
This example provides a fused ring compound (compound 3) having the structure shown below:
the synthetic route for compound 3 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 3 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of Compound 3:
the procedure was followed except that compound I-1 was replaced with compound I-2(22.40 g, 1 eq.) to prepare compound 3(35.24 g, 81% yield).
Elemental analysis: c30H17N30Theoretical value: c, 82.74; h, 3.93; n, 9.65; measured value: c, 82.75; h, 3.95; n, 9.62; HRMS (ESI) M/z (M)+): theoretical value: 435.1372, respectively; measured value: 435.1377.
example 4
This example provides a fused ring compound (compound 4) having a structure represented by the following formula:
the synthetic route for compound 4 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 4 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of Compound 4:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-2(22.40 g, 1 eq) was substituted for compound I-1, with the remainder of the starting materials adjusted to give compound 4(35.68 g, 82% yield).
Elemental analysis: c30H17N3Theoretical value of O: c, 82.74; h, 3.93; n, 9.65; measured value: c, 82.71; h, 3.95; n, 9.66; HRMS (ESI) M/z (M)+): theoretical value: 435.1372, respectively; measured value: 435.1366.
example 5
This example provides a fused ring compound (compound 5) having the structure shown below:
the synthetic route for compound 5 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 5 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of Compound 5:
the procedure was followed except that compound I-1 was replaced with compound I-3(47.61 g, 1 eq.) to prepare compound 5(53.60 g, 78% yield).
Elemental analysis: c49H29N5Theoretical value: c, 85.57; h, 4.25; n, 10.18; measured value: c, 85.58; h, 4.26; n, 10.16; HRMS (ESI) M/z (M)+): theoretical value: 687.2423, respectively; measured value: 687.2429.
example 6
This example provides a fused ring compound (compound 6) having the structure shown below:
the synthetic route for compound 6 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 6 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of Compound 6:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-3(47.61 g, 1 eq) was substituted for compound I-1, with the proportions of the remaining starting materials adjusted to give compound 6(35.68 g, 82% yield).
Elemental analysis: c49H29N5Theoretical value: c, 85.57; h, 4.25; n, 10.18; measured value: c, 85.58; h, 4.25; n, 10.17; HRMS (ESI) M/z (M)+): theoretical value: 687.2423, respectively; measured value: 687.2428.
example 7
This example provides a fused ring compound (compound 7) having the structure shown below:
the synthetic route for compound 7 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 7 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 7:
the procedure was followed except that compound I-4(32.41 g, 1 eq.) was used instead of compound I-1 to prepare compound 7(47.49 g, 82% yield).
Elemental analysis: c41H26Theoretical NOP value: c, 84.96; h, 4.52; n, 2.42; measured value: c, 84.99; h, 4.51; n, 2.40; HRMS (ESI) M/z (M)+): theoretical value: 579.1752, respectively; measured value: 579.1747.
example 8
This example provides a fused ring compound (compound 8) having the structure shown below:
the synthetic route for compound 8 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 8 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 8:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-4(47.61 g, 1 eq) was substituted for compound I-1, with the proportions of the remaining starting materials adjusted to give compound 8(48.07 g, 83% yield).
Elemental analysis: c41H26Theoretical NOP value: c, 84.96; h, 4.52; n, 2.42; measured value: c, 84.98; h, 4.51; n, 2.41; HRMS (ESI) M/z (M)+): theoretical value: 579.1752, respectively; measured value: 579.1759.
example 9
This example provides a fused ring compound (compound 9) having the structure shown below:
the synthetic route for compound 9 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 9 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 9:
the procedure used for the synthesis of compound 1 was different in that compound I-1 was replaced with compound I-5(32.19 g, 1 eq.) and the proportions of the starting materials were adjusted to give compound 9(42.65 g, 80% yield).
Elemental analysis: c35H19NO3Theoretical value of S: c, 78.78; h, 3.59; n, 2.62; measured value: c, 78.80; h, 3.58; n, 2.63; HRMS (ESI) M/z (M)+): theoretical value: 533.1086, respectively; measured value: 533.1088.
example 10
This example provides a fused ring compound (compound 10) having the structure shown below:
the synthetic route for compound 10 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 10 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 10:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was used instead of intermediate 5-E and compound I-5(32.19 g, 1 eq) was used instead of compound I-1, with the remainder of the starting materials adjusted to give compound 10(42.11 g, 79% yield).
Elemental analysis: c35H19NO3Theoretical value of S: c, 78.78; h, 3.59; n, 2.62; measured value: c, 78.80; h, 3.58; n, 2.63; HRMS (ESI) M/z (M)+): theoretical value: 533.1086, respectively; measured value: 533.1092.
example 11
This example provides a fused ring compound (compound 11) having the structure shown below:
the synthetic route for compound 11 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 11 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 11:
the procedure was followed except that compound I-6(23.20 g, 1 eq.) was used instead of compound I-1 to prepare compound 11(35.46 g, 80% yield).
Elemental analysis: c34H21N theoretical value: c, 92.07; h, 4.77; n, 3.16; measured value: c, 92.08; h, 4.78; n, 3.14; HRMS (ESI) M/z (M)+): theoretical value: 443.1674, respectively; measured value: 443.1677.
example 12
This example provides a fused ring compound (compound 12) having the structure shown below:
the synthetic route for compound 12 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 12 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 12:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-6(23.20 g, 1 eq) was substituted for compound I-1, with the proportions of the remaining starting materials adjusted to give compound 12(42.11 g, 79% yield).
Elemental analysis: c34H21N theoretical value: c, 92.07; h, 4.77; n, 3.16; measured value: c, 92.09; h, 4.78; n, 3.13; HRMS (ESI) M/z (M)+): theoretical value: 443.1674, respectively; measured value: 443.1683.
example 13
This example provides a fused ring compound (compound 13) having the structure shown below:
the synthetic route for compound 13 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 13 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 13:
the procedure used for the synthesis of compound 1 was otherwise the same as that used for the synthesis of compound I-1 except that compound I-7(36.00 g, 1 eq.) was used instead of compound I-1, and the proportions of the starting materials were adjusted to give compound 13(43.41 g, 76% yield).
Elemental analysis: c42H25N3Theoretical value: c, 88.24; h, 4.41; n, 7.35; measured value: c, 88.23; h, 4.40; n, 7.37; HRMS (ESI) M/z (M)+): theoretical value: 571.2048, respectively; measured value: 571.2054.
fig. 1 is a graph showing the theoretical calculation results of the HOMO level, the LOMO level, and the energy band gap Eg of compound 13.
Example 14
This example provides a fused ring compound (compound 14) having the structure shown below:
the synthetic route for compound 14 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 14 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 14:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-7(36.00 g, 1 eq) was substituted for compound I-1, with the proportions of the remaining starting materials adjusted to give compound 14(43.98 g, 77% yield).
Elemental analysis: c42H25N3Theoretical value: c, 88.24; h, 4.41; n, 7.35; measured value: c, 88.22; h, 4.42; n, 7.36; HRMS (ESI) M/z (M)+): theoretical value: 571.2048, respectively; measured value: 571.2055.
example 15
This example provides a fused ring compound (compound 15) having the structure shown below:
the synthetic route for compound 15 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 15 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 15:
the procedure was followed except that compound I-1 was replaced with compound I-8(46.31 g, 1 eq.) and the proportions of the starting materials were adjusted to give compound 15(50.57 g, 75% yield).
Elemental analysis: c49H30N4Theoretical value: c, 87.22; h, 4.48; n, 8.30; measured value: c, 87.24; h, 4.50; n, 8.30; HRMS (ESI) M/z (M)+): theoretical value: 674.2470, respectively; measured value: 674.2477.
example 16
This example provides a fused ring compound (compound 16) having the structure shown below:
the synthetic route for compound 16 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 16 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 16:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-8(46.31 g, 1 eq) was substituted for compound I-1, with the proportions of the remaining starting materials adjusted to give compound 16(52.60 g, 78% yield).
Elemental analysis: c49H30N4Theoretical value: c, 87.22; h, 4.48; n, 8.30; measured value: c, 87.23; h, 4.50; n, 8.27; HRMS (ESI) M/z (M)+): theoretical value: 674.2470, respectively; measured value: 674.2467.
example 17
This example provides a fused ring compound (compound 17) having the structure shown below:
the synthetic route for compound 17 is shown below:
the synthesis route of intermediate 5-E is the same as in example 1.
The preparation method of the compound 17 specifically comprises the following steps:
(1) - (5) same as in example 1;
(6) synthesis of compound 17:
the procedure was followed except that compound I-1 was replaced with compound I-9(31.10 g, 1 eq.) to prepare compound 17(39.17 g, 75% yield).
Elemental analysis: c37H22N4Theoretical value: c, 85.04; h, 4.24; n, 10.72; measured value: c, 85.05; h, 4.24; n, 10.71; HRMS (ESI) M/z (M)+): theoretical value: 522.1844, respectively; measured value: 522.1851.
example 18
This example provides a fused ring compound (compound 18) having the structure shown below:
the synthetic route for compound 18 is shown below:
the synthesis route of intermediate 5-E' is the same as that of example 2.
The preparation method of the compound 18 specifically comprises the following steps:
(1) - (5) same as example 2;
(6) synthesis of compound 18:
the same procedure as used for the synthesis of compound 1, except that intermediate 5-E' (29.11 g, 1 eq) was substituted for intermediate 5-E and compound I-9(31.10 g, 1 eq) was substituted for compound I-1, with the remainder of the starting materials adjusted to give compound 18(39.17 g, 75% yield).
Elemental analysis: c37H22N4Theoretical value: c, 85.04; h, 4.24; n, 10.72; measured value: c, 85.05; h, 4.23; n, 10.72; HRMS (ESI) M/z (M)+): theoretical value: 522.1844, respectively; measured value: 522.1839.
example 19
This example provides a fused ring compound (compound 19) having the structure shown below:
the synthetic route for compound 19 is shown below:
wherein the synthetic route of the intermediate 5-F is shown as follows:
the preparation method of the compound 19 specifically comprises the following steps:
(1) synthesis of intermediates 1-F:
the difference of the synthesis method is that 1-tert-butyl-3-bromo-4 iodobenzene (33.79 g, 1 equivalent) is used to replace o-bromoiodobenzene, the proportion of the raw materials is adjusted to obtain intermediate 1-F (23.64 g, 71% yield)
(2) Synthesis of intermediate 2-F:
the difference of the method is that the intermediate 1-F (33.30 g, 1 equivalent) is used to replace the intermediate 1-E, and the ratio of each raw material is adjusted to obtain the intermediate 2-F.
(3) Synthesis of intermediate 3-F:
the same procedure as for the synthesis of intermediate 3-E was followed except that intermediate 2-F (29.91 g, 1 eq.) was used instead of intermediate 2-E, and the proportions of the starting materials were adjusted to give intermediate 3-F (26.17 g, 57% yield).
(4) Synthesis of intermediate 4-F:
the difference from the synthesis of intermediate 4-E was that intermediate 3-F (45.91 g, 1 eq.) was used instead of intermediate 3-E, and the proportions of the starting materials were adjusted to give intermediate 4-F (20.10 g, 53% yield).
(5) Synthesis of intermediate 5-F:
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-F (37.92 g, 1 eq.) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-F (27.43 g, 79% yield).
(6) Synthesis of compound 19:
the procedure was followed for the synthesis of compound 1 except that compound I-7(36.00 g, 1 eq) was used instead of compound I-1 and intermediate 5-F (34.72 g, 1 eq) was used instead of intermediate 5-E, and the proportions of the starting materials were adjusted to give compound 19(51.44 g, 82% yield).
Elemental analysis: c46H33N3Theoretical value: c, 88.01; h, 5.30; n, 6.69; measured value: c, 88.05; h, 5.28; n, 6.67; HRMS (ESI) M/z (M)+): theoretical value: 627.2674, respectively; measured value: 627.2678.
example 20
This example provides a fused ring compound (compound 20) having the structure shown below:
the synthetic route for compound 20 is shown below:
wherein, the synthetic route of the intermediate 5-F' is shown as follows:
the preparation method of the compound 20 specifically comprises the following steps:
(1) synthesis of intermediate 1-F':
the difference of the synthesis method is that 1-tert-butyl-4, 5-dibromonaphthalene (34.19 g, 1 equivalent) is used for replacing o-bromoiodobenzene, the proportion of the raw materials is adjusted to obtain an intermediate 1-F' (21.84 g, the yield is 57%)
(2) Synthesis of intermediate 2-F':
the difference of the method is that the intermediate 1-E is replaced by the intermediate 1-F '(38.31 g, 1 equivalent), and the ratio of the raw materials is adjusted to obtain the intermediate 2-F'.
(3) Synthesis of intermediate 3-F':
the difference from the synthesis of intermediate 3-E was that intermediate 2-F '(34.92 g, 1 eq) was used instead of intermediate 2-E, and the proportions of the starting materials were adjusted to give intermediate 3-F' (26.63 g, 58% yield).
(4) Synthesis of intermediate 4-F':
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-F '(45.91 g, 1 eq) was used instead of intermediate 3-E, and the proportions of the starting materials were adjusted to give intermediate 4-F' (21.24 g, 56% yield).
(5) Synthesis of intermediate 5-F':
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-F '(37.92 g, 1 eq) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-F' (28.12 g, 81% yield).
(6) Synthesis of compound 20:
the procedure was followed except that compound I-7(36.00 g, 1 eq) was used instead of compound I-1 and intermediate 5-F' (34.72 g, 1 eq) was used instead of intermediate 5-E to prepare compound 20(50.81 g, 81% yield) by adjusting the proportions of the starting materials.
Elemental analysis: c46H33N3Theoretical value: c, 88.01; h, 5.30; n, 6.69; measured value: c, 88.03; h, 5.29; n, 6.68; HRMS (ESI) M/z (M)+): theoretical value: 627.2674, respectively; measured value: 627.2670.
example 21
This example provides a fused ring compound (compound 21) having the structure shown below:
the synthetic route for compound 21 is shown below:
wherein the synthetic route of the intermediate 5-G is shown as follows:
the preparation method of the compound 21 specifically comprises the following steps:
(1) synthesis of intermediates 1-G:
the difference of the synthesis method is that 2-bromo-3-iodonaphthalene (33.19G, 1 equivalent) is used for replacing o-bromoiodobenzene, and the proportion of the raw materials is adjusted to obtain intermediate 1-G (19.29G, 59 percent of yield)
(2) Synthesis of intermediates 2-G:
the difference of the method is that the intermediate 1-E is replaced by the intermediate 1-G (32.70G, 1 equivalent) and the ratio of the raw materials is adjusted to obtain the intermediate 2-G.
(3) Synthesis of intermediate 3-G:
the difference from the synthesis of intermediate 3-E was that intermediate 2-G (29.31G, 1 eq.) was used instead of intermediate 2-E, and the proportions of the starting materials were adjusted to give intermediate 3-G (23.10G, 51% yield).
(4) Synthesis of intermediate 4-G:
the difference from the synthesis of intermediate 4-E was that intermediate 3-G (45.30G, 1 eq.) was used instead of intermediate 3-E, and the proportions of the starting materials were adjusted to give intermediate 4-G (19.40G, 52% yield).
(5) Synthesis of intermediate 5-G:
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-G (37.31G, 1 eq.) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-G (27.29G, 80% yield).
(6) Synthesis of compound 21:
the procedure was followed for the synthesis of compound 1 except that compound I-9 (31.10G, 1 eq) was used instead of compound I-1 and intermediate 5-G (34.11G, 1 eq) was used instead of intermediate 5-E, and the proportions of the starting materials were adjusted to give compound 21 (41.20G, 72% yield).
Elemental analysis: c41H24N4Theoretical value: c, 85.99; h, 4.22; n, 9.78; measured value: c, 85.98; h, 4.23; n, 9.78; HRMS (ESI) M/z (M)+): theoretical value: 572.2001, respectively; measured value: 572.2007.
example 22
This example provides a fused ring compound (compound 22) having the structure shown below:
the synthetic route for compound 22 is shown below:
wherein, the synthetic route of the intermediate 5-G' is shown as follows:
the preparation method of the compound 22 specifically comprises the following steps:
(1) synthesis of intermediate 1-G':
the difference from the synthesis method of the intermediate 1-E lies in that 1, 10-dibromobenzonaphthalene (33.59G, 1 equivalent) is used for replacing o-bromoiodobenzene, the proportion of the raw materials is adjusted, and the intermediate 1-G' (19.98G, 53 percent of yield) is obtained
(2) Synthesis of intermediate 2-G':
the difference of the method is that the intermediate 1-E is replaced by the intermediate 1-G '(37.70G, 1 equivalent) and the ratio of the raw materials is adjusted to obtain the intermediate 2-G'.
(3) Synthesis of intermediate 3-G':
the difference from the synthesis of intermediate 3-E is that intermediate 2-G '(34.31G, 1 eq) is used instead of intermediate 2-E, and o-dibromobenzene (23.59G, 1 eq) is used instead of 1, 8-dibromonaphthalene, and the proportions are adjusted to obtain intermediate 3-G' (23.56G, 52% yield).
(4) Synthesis of intermediate 4-G':
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-G '(45.30G, 1 eq) was used instead of intermediate 3-E, and the proportions of the starting materials were adjusted to give intermediate 4-G' (22.01G, 59% yield).
(5) Synthesis of intermediate 5-G':
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-G '(37.31G, 1 eq) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-G' (27.63G, 81% yield).
(6) Synthesis of compound 22:
the procedure was followed for the synthesis of compound 1 except that compound I-9 (31.10G, 1 eq) was used instead of compound I-1 and intermediate 5-G' (34.11G, 1 eq) was used instead of intermediate 5-E, and the proportions of the starting materials were adjusted to give compound 22 (41.20G, 72% yield).
Elemental analysis: c41H24N4Theoretical value: c, 85.99; h, 4.22; n, 9.78; measured value: c, 85.98; h, 4.24; n, 9.77; HRMS (ESI) M/z (M)+): theoretical value: 572.2007, respectively; measured value: 572.2011.
example 23
This example provides a fused ring compound (compound 23) having the structure shown below:
the synthetic route for compound 23 is shown below:
wherein the synthetic route of the intermediate 5-H is shown as follows:
the preparation method of the compound 23 specifically comprises the following steps:
(1) synthesis of intermediates 1-H:
the difference of the synthesis method of the intermediate 1-E is that o-bromoiodobenzene (28.19 g, 1 equivalent) is used for replacing o-bromoiodobenzene, the proportion of the raw materials is adjusted to obtain the intermediate 1-H (18.56 g, 67 percent of yield)
(2) Synthesis of intermediate 2-H:
the difference of the synthesis method is that the intermediate 1-E is replaced by the intermediate 1-H (38.31 g, 1 equivalent), and the intermediate 2-H is obtained by adjusting the proportion of the raw materials.
(3) Synthesis of intermediate 3-H:
the difference from the intermediate 3-E synthesis method is that the intermediate 2-H (34.92 g, 1 equivalent) is used for replacing the intermediate 2-E, 1, 8-dibromo-3, 6-diphenylnaphthalene (43.79 g, 1 equivalent) for replacing 1, 8-dibromonaphthalene, and the raw materials are adjusted in proportion to obtain the intermediate 3-H (28.31 g, 51% yield).
(4) Synthesis of intermediate 4-H:
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-E was replaced with intermediate 3-H (45.91 g, 1 eq.) and the proportions of the starting materials were adjusted to give intermediate 4-H (24.71 g, 52% yield).
(5) Synthesis of intermediate 5-H:
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-H (37.92 g, 1 eq.) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-H (35.46 g, 80% yield).
(6) Synthesis of compound 23:
the procedure was followed using compound I-2(22.40 g, 1 eq.) instead of compound I-1 and intermediate 5-H (44.32 g, 1 eq.) instead of intermediate 5-E to synthesize compound 1, with the proportions of the starting materials adjusted to give compound 23(42.28 g, 72% yield).
Elemental analysis: c42H25N3Theoretical value of O: c, 85.84; h, 4.29; n, 7.15; measured value: c, 85.85; h, 4.30; n, 7.13; HRMS (ESI) M/z (M)+): theoretical value: 587.1998, respectively; measured value: 587.1994.
example 24
This example provides a fused ring compound (compound 24) having the structure shown below:
the synthetic route for compound 24 is shown below:
wherein the synthetic route of the intermediate 5-H' is shown as follows:
the preparation method of the compound 24 specifically comprises the following steps:
(1) synthesis of intermediate 1-H':
the difference of the synthesis method is that 1, 8-dibromo naphthalene (g, 1 equivalent) is used for replacing o-bromoiodobenzene, the proportion of the raw materials is adjusted to obtain an intermediate 1-H' (18.64 g, the yield is 57%)
(2) Synthesis of intermediate 2-H':
the difference of the method is that the intermediate 1-E is replaced by the intermediate 1-H '(32.70 g, 1 equivalent), and the ratio of the raw materials is adjusted to obtain the intermediate 2-H'.
(3) Synthesis of intermediate 3-H':
the difference from the synthesis of intermediate 3-E is that intermediate 2-H '(29.31 g, 1 eq) was used instead of intermediate 2-E, 1, 2-dibromo-4, 5-diphenylbenzene (38.79 g, 1 eq) instead of 1, 8-dibromonaphthalene, and the proportions of the starting materials were adjusted to give intermediate 3-H' (28.87 g, 52% yield).
(4) Synthesis of intermediate 4-H':
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-E was replaced with intermediate 3-H '(55.51 g, 1 eq.) and the proportions of the starting materials were adjusted to give intermediate 4-H' (28.04 g, 59% yield).
(5) Synthesis of intermediate 5-H':
the same procedure as for the synthesis of intermediate 5-E was followed except that intermediate 4-H '(47.52 g, 1 eq) was used instead of intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 5-H' (37.23 g, 84% yield).
(6) Synthesis of compound 24:
the procedure was followed for the synthesis of compound 1 except that compound I-2(22.40 g, 1 eq) was used instead of compound I-1 and intermediate 5-H' (44.32 g, 1 eq) was used instead of intermediate 5-E, and the proportions of the starting materials were adjusted to give compound 24(41.10 g, 70% yield).
Elemental analysis: c42H25N3Theoretical value of O: c, 85.84; h, 4.29; n, 7.15; measured value: c, 85.85; h, 4.30; n, 7.13; HRMS (ESI) M/z (M)+): theoretical value: 587.1998, respectively; measured value: 587.1990.
example 25
This example provides a fused ring compound (compound 25) having the structure shown below:
the synthetic route for compound 25 is shown below:
wherein the synthetic route of the intermediate 4-I is shown as follows:
the preparation method of the compound 25 specifically comprises the following steps:
(1) synthesis of intermediates 1-I:
the difference from the synthesis method of the intermediate 1-E lies in that dibenzothiophene-3-boric acid (22.80 g, 1 equivalent) is used for replacing o-nitrobenzeneboronic acid, 1-bromo-2-iodo-3-nitrobenzene (32.68 g, 1 equivalent) is used for replacing o-bromoiodobenzene, and the proportions of the raw materials are adjusted to obtain the intermediate 1-I (16.47 g, 43% yield).
(2) Synthesis of intermediates 2-I:
the difference from the synthesis method of the intermediate 1-E lies in that 8-chloro-1-naphthalene borate (20.60 g, 1 equivalent) is used for replacing o-nitrobenzeneboronic acid, the intermediate 1-I (38.30 g, 1 equivalent) is used for replacing o-bromoiodobenzene, and the proportion of the raw materials is adjusted to obtain the intermediate 2-I (23.26 g, 50% yield).
(3) Synthesis of intermediate 3-I:
the difference from the synthesis of intermediate 5-E was that intermediate 2-I (46.51 g, 1 eq.) was substituted for intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 3-I (29.45 g, 68% yield).
(4) Synthesis of intermediate 4-I:
the difference from the synthesis of intermediate 4-E was that intermediate 3-E was replaced with intermediate 3-I (43.31 g, 1 eq.) and the proportions of the starting materials were adjusted to give intermediate 4-I (19.06 g, 48% yield).
(5) Synthesis of compound 25:
the same procedure as for the synthesis of compound 1, except that 2-bromo-3-phenylquinoxaline (28.40 g, 1 eq) was used instead of compound I-1 and intermediate 4-I (39.41 g, 1 eq) was used instead of intermediate 5-E, and the proportions of the respective starting materials were adjusted to give compound 25(42.08 g, 70% yield).
Elemental analysis: c42H23N3Theoretical value of S: c, 83.84; h, 3.85; n, 6.98; s, 5.33; measured value: c, 83.85; h, 3.85; n, 6.97; s, 5.33; HRMS (ESI) M/z (M)+): theoretical value: 601.1613, respectively; measured value: 601.1617.
example 26
This example provides a fused ring compound (compound 26) having the structure shown below:
the synthetic route for compound 26 is shown below:
wherein, the synthetic route of the intermediate 4-I' is shown as follows:
the preparation method of the compound 26 specifically comprises the following steps:
(1) synthesis of intermediate 1-I':
the difference from the synthesis method of the intermediate 1-E is that benzonaphtho (1, 2-D) thiophene-5-boric acid (27.81 g, 1 equivalent) is used for replacing o-nitrobenzeneboronic acid, 1-bromo-2-iodo-3-nitrobenzene (32.68 g, 1 equivalent) is used for replacing o-bromoiodobenzene, and the proportion of the raw materials is adjusted to obtain the intermediate 1-I' (20.35 g, 47% yield).
(2) Synthesis of intermediate 2-I':
the difference of the synthesis method of the intermediate 1-E is that o-chlorobenzoic acid (15.60 g, 1 equivalent) is used for replacing o-nitrobenzoic acid, intermediate 1-I '(38.30 g, 1 equivalent) is used for replacing o-bromoiodobenzene, and the proportion of the raw materials is adjusted to obtain intermediate 2-I' (23.72 g, 51% yield).
(3) Synthesis of intermediate 3-I':
the same synthesis as intermediate 5-E was followed except that intermediate 2-I '(46.51 g, 1 eq) was substituted for intermediate 4-E, and the proportions of the starting materials were adjusted to give intermediate 3-I' (28.58 g, 66% yield).
(4) Synthesis of intermediate 4-I':
the same procedure as for the synthesis of intermediate 4-E was followed except that intermediate 3-E was replaced with intermediate 3-I '(43.31 g, 1 eq.) and the proportions of the starting materials were adjusted to give intermediate 4-I' (19.46 g, 49% yield).
(5) Synthesis of compound 26:
the same procedure as for the synthesis of compound 1, except that 2-bromo-3-phenylquinoxaline (28.40 g, 1 eq) was used instead of compound I-1 and intermediate 4-I' (39.41 g, 1 eq) was used instead of intermediate 5-E, and the proportions of the respective starting materials were adjusted to give compound 26(40.28 g, 68% yield).
Elemental analysis: c42H23N3Theoretical value of S: c, 83.84; h, 3.85; n, 6.98; s, 5.33; measured value: c, 83.85; h, 3.85; n, 6.97; s, 5.33; HRMS (ESI) M/z (M)+): theoretical value: 601.1613, respectively; measured value: 601.1620.
example 27
The present embodiment provides an organic electroluminescent device comprising an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode 8, which are sequentially stacked and disposed on a substrate 1, as shown in fig. 2.
The anode 2 in the organic electroluminescent device is made of ITO material;
the material of the hole injection layer 3 is HAT (CN)6Has the following chemical structure:
the material of the hole transport layer 4 is selected from compounds with the following structures:
the material of the light-emitting layer 5 is formed by co-doping a host material and a guest material, wherein the host material is the compound 1 prepared in the embodiment 1, the guest material is the compound RD, the doping mass ratio of the host material to the guest material is 20:1,
the material of the electron transport layer 6 is BPhen, and has the following chemical structure:
the material of the electron injection layer 7 is LiF;
the cathode 8 is made of metal Al.
The preparation method of the organic electroluminescent device comprises the following steps:
(1) substrate cleaning: carrying out ultrasonic treatment on the ITO-coated transparent glass substrate in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are that ethylene glycol solvent is less than or equal to 10wt percent and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1: 1), baking is carried out in a clean environment until water is completely removed, and then ultraviolet light and ozone are used for cleaning.
(2) Evaporating an organic light-emitting functional layer:
placing the glass substrate with the anode layer in a vacuum chamber, and vacuumizing to 1 × 10-6To 2X 10-4Pa, vacuum vapor depositing HAT (CN) on the anode layer film6As a hole injection layer, the evaporation rate is 0.1nm/s, and the evaporation thickness is 100 nm;
a hole transport layer is evaporated on the hole injection layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 500 nm;
the luminescent layer is vapor-plated on the hole transport layer, and the specific preparation method comprises the following steps: carrying out vacuum evaporation on a luminescent host material and an object material in a co-evaporation mode, wherein the evaporation rate of the host material is 0.1nm/s, the evaporation rate of the object material is 0.005nm/s, and the total evaporation film thickness is 20 nm;
vacuum evaporating an electron transport layer on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 300 nm;
vacuum evaporating an electron injection layer on the electron transport layer, wherein the evaporation rate is 0.05nm/s, and the total film thickness is 10 nm;
al is evaporated on the electron injection layer, the evaporation rate is 0.1nm/s, and the total thickness of the evaporated film is 150 nm.
The organic electroluminescent device has simple preparation process and low production cost, and is suitable for industrial production and application.
Example 28
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 2 prepared in example 2 was used as the host material of the light-emitting layer 5.
Example 29
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 3 prepared in example 3 was used as the host material of the light-emitting layer 5.
Example 30
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 4 prepared in example 4 was used as the host material of the light-emitting layer 5.
Example 31
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 5 prepared in example 5 was used as the host material for the light-emitting layer 5.
Example 32
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 6 prepared in example 6 was used as the host material of the light-emitting layer 5.
Example 33
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 7 prepared in example 7 was used as the host material for the light-emitting layer 5.
Example 34
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 8 prepared in example 8 was used as the host material of the light-emitting layer 5.
Example 35
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 9 prepared in example 9 was used as a host material for the light-emitting layer 5.
Example 36
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 10 prepared in example 10 was selected as the host material of the light-emitting layer 5.
Example 37
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 11 prepared in example 11 was used as the host material for the light-emitting layer 5.
Example 38
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 12 prepared in example 12 was used as the host material of the light-emitting layer 5.
Example 39
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 13 prepared in example 13 was used as the host material for the light-emitting layer 5.
Example 40
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 14 prepared in example 14 was used as the host material of the light-emitting layer 5.
EXAMPLE 41
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 15 prepared in example 15 was used as a host material for the light-emitting layer 5.
Example 42
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 16 prepared in example 16 was used as the host material for the light-emitting layer 5.
Example 43
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 17 prepared in example 17 was used as a host material for the light-emitting layer 5.
Example 44
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 18 prepared in example 18 was used as a host material for the light-emitting layer 5.
Example 45
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 19 prepared in example 19 was used as a host material for the light-emitting layer 5.
Example 46
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 20 prepared in example 20 was used as the host material of the light-emitting layer 5.
Example 47
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 21 prepared in example 21 was used as the host material for the light-emitting layer 5.
Example 48
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 22 prepared in example 22 was used as the host material of the light-emitting layer 5.
Example 49
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 23 prepared in example 23 was used as a host material for the light-emitting layer 5.
Example 50
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 24 prepared in example 24 was used as the host material for the light-emitting layer 5.
Example 51
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 25 prepared in example 25 was used as the host material for the light-emitting layer 5.
Example 52
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the compound 26 prepared in example 26 was used as a host material for the light-emitting layer 5.
Comparative example 1
This example provides an organic electroluminescent device, which differs from that provided in example 27 only in that: the host material of the light-emitting layer 5 is a compound CBP, and has the following chemical structure:
test example 1
Measurement of thermal decomposition temperature:
the fused ring compound materials of examples 1 to 26 were subjected to thermal decomposition temperature measurement using a thermogravimetric analyzer (TATGA 55, USA) in a range of room temperature to 600 ℃ at a temperature rise rate of 10 ℃/min, and a temperature at which 5% of weight loss is defined as a thermal decomposition temperature (T.sub.m.) under a nitrogen atmosphered) The measurement results are shown in table 1:
TABLE 1
From the thermal decomposition temperatures of the compound materials obtained by the above tests, it can be seen that the fused ring compound materials prepared in examples 1 to 26 all have higher thermal decomposition temperatures, and can ensure that the materials maintain excellent thermal stability in the device, so that the materials are not easily decomposed and damaged in the device preparation process, and have long service life.
Test example 2
Testing HOMO and LOMO energy levels:
the LUMO energy levels of the fused cyclic compound materials prepared in examples 1 to 26 were measured using an electrochemical workstation using cyclic voltammetry (CV shanghai chen CHI-600E) with a platinum wire (Pt) as a counter electrode and silver/silver chloride (Ag/AgCl) as a reference electrode. Under the nitrogen atmosphere, the test is carried out in methylene chloride electrolyte containing 0.1M tetrabutylammonium hexafluorophosphate at the scanning rate of 100mV/s, the potential calibration is carried out by ferrocene, and the absolute energy level of the potential of the ferrocene in the vacuum state is set as-4.8 eV:
Eg(eV): energy level difference of HOMO-LUMO.
ET1(eV) triplet level.
Triplet state energy level test conditions: fluorescence spectrophotometer (Hitachi F-4600), solution state (toluene as solvent, concentration 2 x 10)-5mol/L) and 78 degrees centigrade.
ET11240/shortest absorption wavelength
The measurement results are shown in table 2:
TABLE 2
From the LUMO level and HOMO level of each compound material obtained in the above tests, it was found that the condensed ring compound materials obtained in examples 1 to 26 were completely separated in HOMO and LOMO levelsThe triplet state energy level is improved while the energy gap width is reduced, and the light-emitting efficiency is reduced due to the fact that energy from an object material to a host material flows backwards. Further, Ar of Compound 11 and Compound 121The radicals being electron-donating groups having a higher HOMO level than the other groups of compounds, and thus Ar1The group is preferably an electron withdrawing group.
Test example 3
The organic electroluminescent devices provided in examples 27 to 52 and comparative example 1 were tested,
the instrument comprises the following steps: the characteristics of the device such as current, voltage, brightness, service life and the like are synchronously tested by adopting a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;
and (3) testing conditions are as follows: the current density is 10mA/cm225 degrees celsius.
The results are shown in Table 3.
TABLE 3
As can be seen from the test data in Table 3, in examples 27 to 52, compared with comparative example 1, the compounds of examples 1 to 26 of the present application as the host material of the light-emitting layer of the organic electroluminescent device can effectively reduce the operating voltage of the device, and at the same time, can improve the light-emitting efficiency of the device. Further, Ar of Compound 11 and Compound 121The group is an electron-donating group, and when it is used as a host material for a light-emitting layer, devices (examples 37 and 38) produced have higher operating voltage and lower light-emitting efficiency than other groups of compounds, and therefore Ar is1The group is preferably an electron withdrawing group.
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 fused ring compound having a structure represented by formula (I) or formula (II):
R1-R14independently of one another, from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl of (a), substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkylamino group of (A), substituted or unsubstituted C2-C60Substituted or unsubstituted C2-C60Alkynylamino, substituted or unsubstituted C1-C60Alkoxy, substituted or unsubstituted C2-C60Alkenyloxy of (a), substituted or unsubstituted C2-C60Alkynyloxy of, substituted or unsubstituted C1-C60Thioalkoxy, substituted or unsubstituted C2-C60Thioalkenyloxy, substituted or unsubstituted C2-C60With a thioalkynyloxy group, substituted or unsubstituted C1-C60With an alkyl boron group, substituted or unsubstituted C2-C60With an alkene boron group, substituted or unsubstituted C2-C60With a boron alkynyl group, substituted or unsubstituted C1-C60Ester group of (1), substituted or unsubstituted C1-C60Amide group of (A), substituted or unsubstituted C4-C60Aryl, substituted or unsubstituted C3-C60Heteroaryl, substituted or unsubstituted C4-C60Aryloxy group of (1), substituted or unsubstituted C4-C60With an aromatic amine group, substituted or unsubstituted C4-C60Of a thioaromatic compoundOxy, substituted or unsubstituted C4-C60An arylboron group of, or
R1-R14Any two to four adjacent groups of which are linked to form one or more groups of rings A,
the ring A is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C60Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring;
Ar1selected from a group P substituted or unsubstituted with one or more substituents selected from:
C4-C60aryl of (C)3-C60Heteroaryl of (A), C4-C60Aryloxy group of (A), C4-C60Aromatic amine group of (2), C4-C60Thioaryloxy of (C)4-C60Aryl boron group of (A), C4-C60Aryl phosphine group of (A), C4-C60Heteroaryloxy of (A), C4-C60Heteroaromatic amino group of (1), C4-C60Thio-heteroaryloxy of (A), C4-C60Heteroaryl boron group of (A), C4-C60The heteroaromatic phosphine group of (1);
the substituents are independently of one another selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4Alkenyl of (a), halogen-substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)3-C12Heteroaryl of (A), C3-C12A heteroaryl amine of (a), halogen-substituted C3-C12Heteroaryl, deuterium substituted C of3-C12The heteroaryl group of (a).
2. The fused ring compound of claim 1,
Ar1is composed of
X1-X5Each independently selected from N or CR15The number of N is 0 to 3,
it is shown that the connecting key is,
R15independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30Arylboron group of (A), substituted or unsubstituted C4-C30An aryl phosphorus group of, or
Two adjacent R15Are connected to form a ring B,
the ring B is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring; or
Ar1Is selected from
It is shown that the connecting key is,
T1-T2independently of one another, selected from the group consisting of the connecting bonds O, S, SO2、CO、NR17、C(R17)2、POR17，
n1 is an integer of 0 to 3, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 4,
R16independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30Arylboron group of (A), substituted or unsubstituted C4-C30An aryl phosphorus group of, or
Two adjacent R16Are connected to form a ring C,
the ring C is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, the heterocycle is a saturated or unsaturated ring,
R17independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30An arylboron group of, or
Two adjacent R17Are connected to form a ring D,
the ring D is selected from a substituted or unsubstituted cyclic 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring; or
Ar1Is composed ofY is NR18Or CR18Or O or S, NR18The number of (a) is 0 to 3,it is shown that the connecting key is,
R18independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C4-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl, substituted or unsubstituted C4-C30Aryloxy group of (1), substituted or unsubstituted C4-C30With an aromatic amine group, substituted or unsubstituted C4-C30Thioaryloxy, substituted or unsubstituted C4-C30An arylboron group of, or
Two adjacent R18Are connected to form a ring E,
the ring E is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C30Aryl or substituted or unsubstituted C3-C30The carbocyclic ring isA saturated or unsaturated ring, and the heterocyclic ring is a saturated or unsaturated ring.
3. The fused ring compound of claim 1 or 2,
Ar1selected from the group consisting of19A substituted or unsubstituted group F selected from:
the substituent R19Independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4Alkenyl of (a), halogen-substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)2-C12Heteroaryl of (A), C2-C12A heteroaryl amine of (a), halogen-substituted C2-C12Heteroaryl, deuterium substituted C of2-C12The heteroaryl group of (a);
preferably, the substituent R19Are connected with each otherIndependently selected from hydrogen, deuterium, halogen, methyl, deuterated methyl, trifluoromethyl, ethyl, propyl, tert-butyl, cyano, vinyl, phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl or grate, benzofuranyl, benzothienyl, carbazolyl,
wherein,indicating a bond, ＊ indicating a binding site.
4. The fused ring compound of any one of claims 1-3, wherein Ar is Ar1Are electron withdrawing groups.
5. A fused ring compound according to any one of claims 1 to 4,
R1-R14independently of one another, from hydrogen, deuterium, halogen, nitro, cyano, C1-C4Alkyl, halogen substituted C1-C4Alkyl, deuterium substituted C1-C4Alkyl of (C)1-C4Alkoxy group of (C)1-C4Alkenyl of (a), halogen-substituted C1-C4Alkenyl, deuterium substituted C1-C4Alkenyl of, C6-C12Aryl of (C)6-C12Aryloxy group of (A), C6-C12Arylamino, halogen-substituted C6-C12Aryl, deuterium substituted C of6-C12Aryl of (C)2-C12Heteroaryl of (A), C2-C12A heteroaryl amine of (a), halogen-substituted C2-C12Heteroaryl, deuterium substituted C of2-C12The heteroaryl group of (a); or
R1-R14Any two to four adjacent groups of which are linked to form one or more groups of rings A,
the ring A is selected from a substituted or unsubstituted 3-7 membered carbocyclic ring, a substituted or unsubstituted 3-7 membered heterocyclic ring, a substituted or unsubstituted C4-C12Aryl of (2)Or substituted or unsubstituted C3-C12The carbocycle is a saturated or unsaturated ring, and the heterocycle is a saturated or unsaturated ring;
preferably, R1-R14Independently of one another, from the group consisting of hydrogen, deuterium, halogen, methyl, ethyl, propyl, n-butyl, tert-butyl, trifluoromethyl, cyano, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, adamantyl, bornyl, triphenylene, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthryl, benzophenanthrenyl, pyrenyl, chrysenyl, tetracenyl, picenyl, perylenyl, pentylphenyl, pentacenyl, rubinyl, coronenyl, ovaphenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, thienyl, furyl, quinolyl, carbazolyl, pyranyl, thiopyranyl, phthalazinyl, phenazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, indolyl, indolocarbazolyl, phenanthridinyl, acridinyl, terphenyl, phenanthridinyl, phenanthrenyl, perimidine group, pteridinyl group, quinazolinyl group, quinoxalinyl group, cinnolinyl group, phenanthroline group, carbolinyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiapyrrolyl group, benzonaphthothiapyrrolyl group, dinaphthothiazolyl group, benzimidazolyl group, imidazopyridinyl group.
6. A fused ring compound according to any one of claims 1 to 5, having a molecular structure represented by any one of:
7. a process for the preparation of a fused ring compound as claimed in any one of claims 1 to 6,
the synthesis steps of the compound shown in the formula (I) are as follows:
taking a compound shown in a formula (A) and a compound shown in a formula (B) as initial raw materials, and carrying out Suzuki coupling reaction to obtain an intermediate 1-A; carrying out coupling reaction on the intermediate 1-A and a compound shown as a formula (C) to obtain an intermediate 2-A; carrying out coupling reaction on the intermediate 2-A and a compound shown as a formula (D) to obtain an intermediate 3-A; carrying out coupling and ring-closing reaction on the intermediate 3-A to obtain an intermediate 4-A; carrying out nitro reduction and ring closure reaction on the intermediate 4-A to obtain an intermediate 5-A; carrying out coupling reaction on the intermediate 5-A and a compound shown as a formula (E) to obtain a compound shown as a formula (I);
the synthetic route of the compound shown in the formula (I) is shown as follows:
the synthesis steps of the compound shown in the formula (II) are as follows:
taking a compound shown in a formula (F) and a compound shown in a formula (G) as initial raw materials, and carrying out Suzuki coupling reaction to obtain an intermediate 1-B; carrying out coupling reaction on the intermediate 1-B and a compound shown as a formula (H) to obtain an intermediate 2-B; carrying out coupling reaction on the intermediate 2-B and a compound shown as a formula (J) to obtain an intermediate 3-B; the intermediate 3-B is subjected to coupling ring-closing reaction to obtain an intermediate 4-B; carrying out nitro reduction and ring closure reaction on the intermediate 4-B to obtain an intermediate 5-B; carrying out coupling reaction on the intermediate 5-B and a compound shown as a formula (K) to obtain a compound shown as a formula (II);
the synthetic route of the compound shown in the formula (II) is shown as follows:
8. an electronic device comprising a substrate, a first electrode formed on the substrate, a second electrode, an organic layer provided between the first electrode and the second electrode, the organic layer comprising the fused ring compound according to any one of claims 1 to 6;
the organic layer comprises at least one of a luminescent layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer;
the light-emitting layer includes a host material containing the condensed ring compound according to any one of claims 1 to 6 and a dopant material.
9. A display device characterized by comprising the electronic device according to claim 8.
10. A lighting device comprising the electronic device of claim 8.
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| CN114349741A (en) * | 2021-12-31 | 2022-04-15 | 武汉天马微电子有限公司 | Organic compound and application thereof |
| CN114349741B (en) * | 2021-12-31 | 2023-03-24 | 武汉天马微电子有限公司 | Organic compound and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111056988A (en) | 2020-04-24 |
| CN111039850B (en) | 2022-02-25 |
| CN111039850A (en) | 2020-04-21 |
| CN111056988B (en) | 2021-10-15 |
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