WO2004005406A2 - Charge transport compositions on the basis of triarylmethanes and their use in electronic devices - Google Patents
Charge transport compositions on the basis of triarylmethanes and their use in electronic devices Download PDFInfo
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- WO2004005406A2 WO2004005406A2 PCT/US2003/021612 US0321612W WO2004005406A2 WO 2004005406 A2 WO2004005406 A2 WO 2004005406A2 US 0321612 W US0321612 W US 0321612W WO 2004005406 A2 WO2004005406 A2 WO 2004005406A2
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- 239000000203 mixture Substances 0.000 title claims abstract description 81
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- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 235000010290 biphenyl Nutrition 0.000 claims description 26
- 239000004305 biphenyl Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical class 0.000 claims description 11
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- 229910052799 carbon Inorganic materials 0.000 claims description 9
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- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- -1 siloxanes Chemical class 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001931 aliphatic group Chemical group 0.000 claims description 3
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- 125000004474 heteroalkylene group Chemical group 0.000 claims description 3
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- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 2
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ARABZLFYTAEJHG-UHFFFAOYSA-N n,n-dibenzyl-3-methylaniline Chemical compound CC1=CC=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 ARABZLFYTAEJHG-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
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- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
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- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Definitions
- the invention further relates to photoactive electronic devices in which there is at least one active layer comprising such charge transport compositions.
- organic photoactive electronic devices such as light-emitting diodes (“OLED”), that make up OLED displays
- the organic active layer is sandwiched between two electrical contact layers in an OLED display.
- OLED light-emitting diodes
- the organic photoactive layer emits light through the light- transmitting electrical contact layer upon application of a voltage across the electrical contact layers.
- organic electroluminescent compounds As the active component in light-emitting diodes. Simple organic molecules, conjugated polymers, and organometallic complexes have been used.
- Devices which use photoactive materials frequently include one or more charge transport layers, which are positioned between the photoactive (e.g., light-emitting) layer and one of the contact layers.
- a hole transport layer may be positioned between the photoactive layer and the hole-injecting contact layer, also called the anode.
- An electron transport layer may be positioned between the photoactive layer and the electron-injecting contact layer, also called the cathode.
- the present invention is directed to a charge transport composition
- a charge transport composition comprising a triarylmethane having Formula I, shown in Figure 1 , wherein: Ar1 can be the same or different at each occurrence and is selected from aryl and heteroaryl; R1 can be the same or different at each occurrence and is selected from H, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a Fb, and CgHcFd,; or adjacent R " !
- X can be the same or different at each occurrence and is selected from R1 , alkenyl, alkynyl, N(R ) 2 , OR1 , OC n H a F b , OC 6 H c F d , halide, NO 2 , OH, CN, and COOR 1 ;
- the present invention is directed to a charge transport composition
- a charge transport composition comprising the above triarylmethane, with the proviso that there is at least one substituent on an aromatic group selected from F, C n H a Fb, OC n H a Fb, C ⁇ HcFci, and OCgHcF ⁇ ].
- the present invention is directed to a charge transport composition with at least one triarylmethane carbon, having Formula II shown in Figure 2, wherein:
- R2 is the same or different at each occurrence and is selected from arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene, with the proviso that when R 2 is arylenealkylene or heteroarylenealkylene, an arylene end is attached to the triarylmethane carbon;
- Q is selected from a single bond and a multivalent group; m is an integer equal to at least 2; p is 0 or 1 , with the proviso that when p is 0, Q is a multivalent group that is arylene or heteroarylene; and Ar 1 , R1 , a through d, and n are as defined above.
- the present invention is directed to an electronic device having at least one layer comprising a material selected from Formulae I and II, shown in Figures 1 and 2, wherein Ar ⁇ , R1 , R 2 , Q, X, a through d, m, n, and p are as defined above, with the proviso that in Formula I when XsAr ⁇ is p-methylphenylene, R1 is not ethyl.
- charge transport composition is intended to mean material that can receive a charge from an electrode and facilitate its movement through the thickness of the material with relatively high efficiency and small loss of charge.
- Hole transport compositions are capable of receiving a positive charge from an anode and transporting it.
- Electron transport compositions are capable of receiving a negative charge from a cathode and transporting it.
- anti-quenching composition is intended to mean a material which prevents, retards, or diminishes both the transfer of energy and the transfer of an electron to or from the excited state of the photoactive layer to an adjacent layer.
- photoactive refers to any material that exhibits electroluminescence, photoluminescence, and/or photosensitivity.
- HOMO refers to the highest occupied molecular orbital of a compound.
- LUMO refers to the lowest unoccupied molecular orbital of a compound.
- group is intended to mean a part of a compound, such as a substituent in an organic compound. The prefix “hetero” indicates that one or more carbon atoms has been replaced with a different atom.
- alkyl is intended to mean a group derived from an aliphatic hydrocarbon having one point of attachment, which group may be unsubstituted or substituted.
- heteroalkyl is intended to mean a group derived from an aliphatic hydrocarbon having at least one heteroatom and having one point of attachment, which group may be unsubstituted or substituted.
- alkylene is intended to mean a group derived from an aliphatic hydrocarbon and having two or more points of attachment.
- heteroalkylene is intended to mean a group derived from an aliphatic hydrocarbon having at least one heteroatom and having two or more points of attachment.
- alkylene is intended to mean a group derived from an aliphatic hydrocarbon and having two or more points of attachment.
- heteroalkylene is intended to mean a group derived from an aliphatic hydrocarbon having at least one heteroatom and having two or more points of attachment.
- alkenyl is intended to mean a group derived from a hydrocarbon having one or more carbon- carbon double bonds and having one point of attachment, which group may be unsubstituted or substituted.
- alkynyl is intended to mean a group derived from a hydrocarbon having one or more carbon- carbon triple bonds and having one point of attachment, which group may be unsubstituted or substituted.
- alkenylene is intended to mean a group derived from a hydrocarbon having one or more carbon- carbon double bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
- alkynylene is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon triple bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
- heteroalkenyl is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon double bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
- alkynylene is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon triple bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
- heteroalkenyl is intended to mean a group derived from an aromatic hydrocarbon having one point of attachment, which group may be unsubstituted or substituted.
- aryl is intended to mean a group derived from an aromatic group having at least one heteroatom and having one point of attachment, which group may be unsubstituted or substituted.
- arylalkylene is intended to mean a group derived from an alkyl group having an aryl substituent, which group may be further unsubstituted or substituted.
- heteroarylalkylene is intended to mean a group derived from an alkyl group having a heteroaryl substituent, which group may be further unsubstituted or substituted.
- arylene is intended to mean a group derived from an aromatic hydrocarbon having two points of attachment, which group may be unsubstituted or substituted.
- heteroarylene is intended to mean a group derived from an aromatic group having at least one heteroatom and having two points of attachment, which group may be unsubstituted or substituted.
- arylenealkylene is intended to mean a group having both aryl and alkyl groups and having one point of attachment on an aryl group and one point of attachment on an alkyl group.
- heteroarylenealkylene is intended to mean a group having both aryl and alkyl groups and having one point of attachment on an aryl group and one point of attachment on an alkyl group, and in which there is at least one heteroatom. Unless otherwise indicated, all groups can be unsubstituted or substituted.
- adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
- adjacent R groups is used to refer to R groups that are next to each other in a chemical formula (i.e., R groups that are on atoms joined by a bond).
- the term "compound” is intended to mean an electrically uncharged substance made up of molecules that further consist of atoms, wherein the atoms cannot be separated by physical means.
- ligand is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion.
- complex when used as a noun, is intended to mean a compound having at least one metallic ion and at least one ligand.
- polymeric is intended to encompass oligomeric species and include materials having 2 or more monomeric units.
- the IUPAC numbering system is used throughout, where the groups from the Periodic Table are numbered from left to right as 1 through 18 (CRC st
- Figure 2 shows Formula II for a charge transport composition of the invention.
- Figure 3 shows Formulae l(a) through l(s) for a charge transport composition of the invention.
- Figure 4 shows Formulae lll(a) through lll(h) for a multidentate linking group.
- Figure 5 shows Formulae ll(a) through ll(f) for a charge transport composition of.the invention.
- Figure 6 shows Formulae IV(a) through IV(e) for electroluminescent iridium complexes.
- FIG 7 is a schematic diagram of a light-emitting diode (LED).
- Figure 8 is shows formulae for known hole transport materials.
- Figure 9 is a schematic diagram of a testing device for an LED.
- the triarylmethane compounds represented by Formula I, shown in Figure 1 have particular utility as hole transport compositions.
- the compound bis(4-N,N-diethylamino-2-methylphenyl)-4- methylphenylmethane (MPMP) has been disclosed to be a suitable hole transport composition in Petrov et al., Published PCT application WO 02/02714.
- Other triarylmethane derivatives have not been used in OLED devices.
- n is an integer. In one embodiment, n is an integer from 1 through 20. In one embodiment, n is an integer from 1 through 12.
- Ar is selected from phenyl and biphenyl groups, which may have one or more carbon atoms replaced with a heteroatom. All of these groups may further be substituted. Examples of substituents include, but are not limited to, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a Fb, and C ⁇ HcFd, where a through d and n are as defined above.
- the Ar ⁇ in the XsAr ⁇ group is selected from phenyl, biphenyl, pyridyl, and bipyridyl, which may further be substituted.
- substituents include, but are not limited to, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a Fb, and C ⁇ HcFd, where a through d and n are as defined above.
- X is a fused heteroaromatic ring group.
- groups include, but are not limited to, N-carbazoles, benzodiazoles, and benzotriazoles.
- N(R ⁇ )2 is a fused heteroaromatic ring group.
- Examples of such groups include, but are not limited to, carbazoles, benzodiazoles, and benzotriazoles.
- R1 is selected from alkyl groups having 1 through 12 carbon atoms, phenyl and benzyl. In one embodiment, there is at least one substituent on an aryl ring selected from F, C n H a Fb, OC n H a Fb, C ⁇ HcFd, and OC ⁇ HcFd, where a through d and n are as defined above.
- suitable hole transport compounds of the invention include, but are not limited to, those given as Formulae l(a) through l(t), shown in Figure 3.
- the compositions represented by Formula I can be prepared using standard synthetic organic techniques, as illustrated in the examples.
- the compounds can be applied as thin films by evaporative techniques or conventional solution processing methods.
- solution processing refers to the formation of films from a liquid medium.
- the liquid medium can be in the form of a solution, a dispersion, an emulsion, or other forms.
- Typical solution processing techniques include, for example, solution casting, drop casting, curtain casting, spin-coating, screen printing, inkjet printing, gravure printing, and the like.
- Tg of the compounds In some cases it is desirable to increase the Tg of the compounds to improve stability, coatability, and other properties.
- This can be accomplished by linking together two or more of the compounds with a linking group to form compounds having Formula II, shown in Figure 2.
- the carbon atom shown as "C” is referred to as a "triarylmethane carbon".
- Q can be a single bond or a multivalent linking group, having two or more points of attachment.
- the multivalent linking group can be a hydrocarbon group with two or more points of attachment, and can be aliphatic or aromatic.
- the multivalent linking group can be a heteroalkyl or heteroaromatic group, where the heteroatoms can be, for example, N, O, S, or Si.
- multivalent groups include, but are not limited to, aikylene, alkenylene, and alkynylene groups, and analogous compounds with heteroatoms; single, multiple-ring, and fused-ring aromatics and heteroaromatics; arylamines, such as triarylamines; silanes and siloxanes. Additional examples of multivalent Q groups are given in Figure 4 as Formulae lll(a) through I ⁇ I(h).
- any of the carbons may be linked to a charge transport moiety.
- any of the Si atoms can be linked to a charge transport moiety.
- Heteroatoms such as Ge and Sn can also be used.
- the linking group can also be and n are as defined above.
- n is an integer. In one embodiment, n is an integer from
- n is an integer from 1 through 12.
- Ar1 is selected from phenyl and biphenyl groups, which may have one or more carbon atoms replaced with a heteroatom. All of these groups may further be substituted. Examples of substituents include, but are not limited to, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a Fb, and C ⁇ HcFd, where a through d and n are as defined above.
- N(R1 )2 is a fused heteroaromatic ring group.
- Examples of such groups include, but are not limited to, carbazoles, benzodiazoles, and benzotriazoles.
- R1 is selected from alkyl groups having 1 through 12 carbon atoms, phenyl and benzyl.
- R 2 is selected from phenyl, biphenyl, pyridyl, and bipyridyl, which may further be substituted.
- substituents include, but are not limited to, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a Fb, and C ⁇ HcF i, where a through d and n are as defined above.
- at least one Rl is selected from F, C n H a Fb,
- compositions represented by Formula II can be prepared using standard synthetic organic techniques, as illustrated in the examples.
- the compounds can be applied as thin films by evaporative techniques or conventional solution processing methods.
- solution processing refers to the formation of films from a liquid medium.
- the liquid medium can be in the form of a solution, a dispersion, an emulsion, or other forms.
- Typical solution processing techniques include, for example, solution casting, drop casting, curtain casting, spin-coating, screen printing, inkjet printing, gravure printing, and the like.
- the present invention also relates to an electronic device comprising at least one of the charge transport compositions of the invention.
- the charge transport compositions can be in a separate layer, positioned between a photoactive layer and one electrode. Alternatively, the charge transport compositions of the invention can be in the photoactive layer.
- a typical device structure is shown in Figure 7.
- the device 100 has an anode layer 110 and a cathode layer 160. Adjacent to the anode is a layer 120 comprising hole transport material. Adjacent to the cathode is a layer 140 comprising an electron transport and/or anti- quenching material.
- the photoactive layer 130 Between the hole transport layer and the electron transport and/or anti-quenching layer is the photoactive layer 130. As an option, devices frequently use another electron transport layer 150, next to the cathode. Layers 120, 130, 140, and 150 are individually and collectively referred to as the active layers.
- the photoactive layer 130 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell), a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
- an applied voltage such as in a light-emitting diode or light-emitting electrochemical cell
- a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage
- photodetectors include photoconductive cells, photoresistors, photoswitches, phototransistors, and phototubes, and photovoltaic cells, as these terms are describe in Markus, John, Electronics and Nucleonics Dictionary, 470 and 476 (McGraw-Hill, Inc. 1966).
- the triarylmethane derivative compounds of the invention are particularly useful as the hole transport layer 120, and as a charge conducting host in the photoactive layer, 130.
- the other layers in the device can be made of any materials which are known to be useful in such layers.
- the anode 110 is an electrode that is particularly efficient for injecting positive charge carriers. It can be made of, for example materials containing a metal, mixed metal, alloy, metal oxide or mixed-metal oxide, or it can be a conducting polymer, and mixtures thereof. Suitable metals include the Group 11 metals, the metals in Groups 4, 5, and 6, and the Group 8-10 transition metals.
- the anode 110 may also comprise an organic material such as polyaniline as described in "Flexible light-emitting diodes made from soluble conducting polymer," Nature vol. 357, pp 477-479 (11 June 1992). At least one of the anode and cathode should be at least partially transparent to allow the generated light to be observed.
- the photoactive layer 130 include all known electroluminescent materials. Organometallic electroluminescent compounds are preferred. The most preferred compounds include cyclometalated iridium and platinum electroluminescent compounds and mixtures thereof.
- Electroluminescent emissive layers comprising a charge carrying host material and a phosphorescent platinum complex have been described by Thompson et al., in U.S. Patent 6,303,238, Bradley et al., in Synth. Met. (2001), 116 (1- 3), 379-383, and Campbell et al., in Phys. Rev. B, Vol. 65 085210. Examples of a few suitable iridium complexes are given in Figure 6, as Formulae IV(a) through IV(e). Analogous tetradentate platinum complexes can also be used. These electroluminescent complexes can be used alone, or doped into charge-carrying hosts, as noted above.
- the molecules of the present invention in addition to being useful in the hole transport layer 120, may also act as a charge carrying host for the emissive dopant in the photoactive layer 130.
- electron transport materials which can be used in layer 140 and/or layer 150 include metal chelated oxinoid compounds, such as tris(8-hydroxyquinoiato)aIuminum (Alq3); and azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (PBD) and 3-(4- biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1 ,2,4-triazole (TAZ), and mixtures thereof.
- metal chelated oxinoid compounds such as tris(8-hydroxyquinoiato)aIuminum (Alq3)
- azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (PBD) and 3-(4- biphenylyl)-4-phenyl-5-(4-t-butylphen
- the cathode 160 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
- the cathode can be any metal or nonmetal having a lower work function than the anode.
- Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides. Materials such as aluminum, indium, calcium, barium, samarium and magnesium, as well as combinations, can be used.
- Li-containing organometallic compounds, LiF, and Li 2 O can also be deposited between the organic layer and the cathode layer to lower the operating voltage.
- anode 110 there can be a layer (not shown) between the anode 110 and hole transport layer 120 to facilitate positive charge transport and/or band- gap matching of the layers, or to function as a protective layer.
- Layers that are known in the art can be used.
- any of the above- described layers can be made of two or more layers.
- some or all of anode layer 110, the hole transport layer 120, the electron transport layers 140 and 150, and cathode layer 160 may be surface treated to increase charge carrier transport efficiency.
- the choice of materials for each of the component layers is preferably determined by balancing the goals of providing a device with high device efficiency with device operational lifetime.
- each functional layer may be made up of more than one layer.
- the device can be prepared by a variety of techniques, including sequentially vapor depositing the individual layers on a suitable substrate.
- Substrates such as glass and polymeric films can be used.
- Conventional vapor deposition techniques can be used, such as thermal evaporation, chemical vapor deposition, and the like.
- the organic layers can be applied from solutions or dispersions in suitable solvents, using any conventional coating or printing technique, including but not limited to spin-coating, dip-coating, roll-to-roll techniques, ink-jet printing, screen- printing, gravure printing and the like.
- the different layers will have the following range of thicknesses: anode 110, 500-5000A, preferably 1000-2000A; hole transport layer 120, 50-2000A, preferably 200-1000A; photoactive layer 130, 10-2000 A, preferably 100-1 OOOA; electron transport layer 140 and 150, 50-2000A, preferably 100-1000A; cathode 160, 200-1 OOOOA, preferably 300-5000A.
- the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer.
- the thickness of the electron-transport layer should be chosen so that the electron-hole recombination zone is in the light-emitting layer.
- the desired ratio of layer thicknesses will depend on the exact nature of the materials used.
- the triarylmethane derivative compounds of the invention may be useful in applications other than OLEDs.
- these compositions may be used in photovoltaic devices for solar energy conversion. They may also be used in field effect transistor for smart card and thin film transistor (TFT) display driver applications.
- TFT thin film transistor
- EXAMPLE 1 This example illustrates the preparation of triarylmethane hole transport compositions, shown in Figure 3.
- Compound l(f) 32.6g of N,N-diethyl-m-toluidine and 12.4g p- fluorobenzaldehyde were mixed in 30mL ethanol and 10mL cone. HCI. This mixture was gently refluxed under nitrogen for 16hrs at which point the mixture was cooled and poured into 250mL distilled water.
- nmr 7.50(s); 6.4(m);6.35(m);5.50(s);3.23(q);2.02(s);1.05(t); 19F nmr: -108.1 (s); - 108.5(s).
- EXAMPLE 2 This examples illustrates the preparation of a hole transport compound having multiple triarylmethane groups, Compound ll(c) in Figure 5. Step 1 :
- Thin film OLED devices including a hole transport layer (HT layer), electroluminescent layer (EL layer) and at least one electron transport and/or anti-quenching layer (ET/AQ layer) were fabricated by the thermal evaporation technique.
- An Edward Auto 306 evaporator with oil diffusion pump was used.
- the base vacuum for all of the thin film deposition was in the range of 10 ⁇ 6 torr.
- the deposition chamber was capable of depositing five different films without the need to break up the vacuum.
- ITO indium tin oxide
- Thin Film Devices, Inc was used. These ITO's are based on Corning 1737 glass coated with 1400A ITO coating, with sheet resistance of 30 ohms/square and 80% light transmission.
- the patterned ITO substrates were then cleaned ultrasonically in aqueous detergent solution. The substrates were then rinsed with distilled water, followed by isopropanol, and then degreased in toluene vapor for ⁇ 3 hours.
- the cleaned, patterned ITO substrate was then loaded into the vacuum chamber and the chamber was pumped down to 10"6 torr.
- the substrate was then further cleaned using an oxygen plasma for about 5-10 minutes.
- multiple layers of thin films were then deposited sequentially onto the substrate by thermal evaporation.
- patterned metal electrodes of Al or LiF and Al were deposited through a mask.
- the thickness of the film was measured during deposition using a quartz crystal monitor (Sycon STC-200). All film thickness reported in the Examples are nominal, calculated assuming the density of the material deposited to be one.
- the completed OLED device was then taken out of the vacuum chamber and characterized immediately without encapsulation.
- Table 1 summarizes the devices made with the hole transport compositions of the invention, and with the comparative hole transport compounds shown in Figure 8.
- emitting layer was the iridium complex from Example 3, having the thickness indicated.
- the electron transport layer 140 was 4,7-diphenyl-1 ,10-phenanthroline, DPA.
- electron transport layer 150 was tris(8-hydroxyquinolato)aluminum(lll), Alq, each having the thicknesses given.
- the cathode was a layer of Al or a dual layer of LiF/AI, with the thicknesses given.
- the OLED samples were characterized by measuring their (1) current-voltage (l-V) curves, (2) electroluminescence radiance versus voltage, and (3) electroluminescence spectra versus voltage.
- the apparatus used, 200 is shown in Figure 9.
- the l-V curves of an OLED sample, 220 were measured with a Keithley Source-Measurement Unit Model 237, 280.
- the electroluminescence radiance (in the unit of cd/rr)2) vs. voltage was measured with a Minolta LS-110 luminescence meter, 210, while the voltage was scanned using the Keithley SMU.
- the electroluminescence spectrum was obtained by collecting light using a pair of lenses, 230, through an electronic shutter, 240, dispersed through a spectrograph, 250, and then measured with a diode array detector, 260. All three measurements were performed at the same time and controlled by a computer, 270.
- the efficiency of the device at certain voltage is determined by dividing the electroluminescence radiance of the LED by the current density needed to run the device. The unit is in cd/A.
- EXAMPLE 6 This example illustrates the preparation of Compound ll(d) in Figure 5.
- Og m-diethylamino-toluene were mixed in 55mL ethanol and 18mL concentrated HCI. The mixture was then gently refluxed under nitrogen for 60hrs. The resulting material was poured into 100mL water and the pH was adjusted to 8 with sodium hydroxide solution (1 N). The ethanol solvent was rotovaporated and the aqueous supernatant was decanted from the greenish organic layer. The organic layer was washed with 100mL distilled water and then triturated with dry ethanol until it became a greenish solid.
- the trialdehyde material 2.6g was combined with 8.1g m- diethylamino-toluene and mixed in 7.5mL ethanol and 2.5mL concentrated HCI. The mixture was then gently refluxed under nitrogen for 48hrs. The resulting material was poured into 25mL water and the pH was adjusted to 8 with sodium hydroxide solution (1 N). The ethanol solvent was rotovaporated and the aqueous supernatant was decanted from the olive green organic layer. The organic layer was washed with 100mL distilled water and then triturated with dry ethanol until it became a tan colored solid.
- the trialdehyde material 3.8g was combined with 9.8g m- diethylamino-toluene and mixed in 9mL ethanol and 3mL concentrated HCI. The mixture was then gently refluxed under nitrogen for 48hrs. The resulting material was poured into 25mL water and the pH was adjusted to 8 with sodium hydroxide solution (1 N). The ethanol solvent was rotovaporated and the aqueous supernatant was decanted from the olive green organic layer. The organic layer was washed with 100mL distilled water and then triturated with dry ethanol until it became a tan colored solid.
- the aldehyde precursor A was isolated by extraction with CH2CI2 as a yellow solid, which can be purified by washing with hexane to give the pure product in 90% yield (2.97 g).
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Indole Compounds (AREA)
- Photovoltaic Devices (AREA)
- Photoreceptors In Electrophotography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CA002492686A CA2492686A1 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions on the basis of triarylmethanes and their use in electronic devices |
JP2004520121A JP2005533341A (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions based on triarylmethane and their use in electronic devices |
AU2003251850A AU2003251850A1 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions on the basis of triarylmethanes and their use in electronic devices |
EP03763459A EP1532209A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions and electronic devices made with such compositions |
Applications Claiming Priority (4)
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US39476702P | 2002-07-10 | 2002-07-10 | |
US60/394,767 | 2002-07-10 | ||
US45827703P | 2003-03-28 | 2003-03-28 | |
US60/458,277 | 2003-03-28 |
Publications (2)
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WO2004005406A2 true WO2004005406A2 (en) | 2004-01-15 |
WO2004005406A3 WO2004005406A3 (en) | 2004-05-21 |
Family
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Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2003/021617 WO2004006352A2 (en) | 2002-07-10 | 2003-07-09 | Electronic devices made with electron transport and/or anti-quenching layers |
PCT/US2003/021612 WO2004005406A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions on the basis of triarylmethanes and their use in electronic devices |
PCT/US2003/021618 WO2004006355A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions which are quinazoline derivatives and electronic devices made with such compositions |
PCT/US2003/021613 WO2004006354A2 (en) | 2002-07-10 | 2003-07-09 | Polymeric charge transport compositions and electronic devices made with such compositions |
PCT/US2003/021610 WO2004005288A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions comprising fluorinated phenanthroline derivatives |
Family Applications Before (1)
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PCT/US2003/021617 WO2004006352A2 (en) | 2002-07-10 | 2003-07-09 | Electronic devices made with electron transport and/or anti-quenching layers |
Family Applications After (3)
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PCT/US2003/021618 WO2004006355A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions which are quinazoline derivatives and electronic devices made with such compositions |
PCT/US2003/021613 WO2004006354A2 (en) | 2002-07-10 | 2003-07-09 | Polymeric charge transport compositions and electronic devices made with such compositions |
PCT/US2003/021610 WO2004005288A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions comprising fluorinated phenanthroline derivatives |
Country Status (10)
Country | Link |
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US (15) | US20040097725A1 (en) |
EP (5) | EP1520308A2 (en) |
JP (5) | JP2006505115A (en) |
KR (3) | KR101011883B1 (en) |
CN (5) | CN1666577A (en) |
AU (5) | AU2003251850A1 (en) |
CA (5) | CA2492692A1 (en) |
HK (2) | HK1079900A1 (en) |
TW (5) | TWI330645B (en) |
WO (5) | WO2004006352A2 (en) |
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