Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12522565-B2
Application number	US-202217672934-A
Country	US
Kind code	B2
Filing date	Feb 16, 2022
Priority date	Oct 25, 2019
Publication date	Jan 13, 2026
Grant date	Jan 13, 2026

Abstract

High performance OLED that includes deuterated compounds in the emissive layer are disclosed. The OLED includes an anode; a cathode; and an emissive layer, disposed between the anode and the cathode. In the OLED, the emissive layer includes a first phosphorescent emitter and a first host; the first phosphorescent emitter is a metal complex; the first host is partially or fully deuterated; and at least one additional condition is true.

First claim

What is claimed is:

1 . An organic electroluminescent device (OLED) comprising:
an anode; a cathode; and an emissive layer, disposed between the anode and the cathode; wherein the emissive layer comprises a first phosphorescent emitter and a first host; wherein the first phosphorescent emitter is a metal complex; wherein the first host is partially or fully deuterated; wherein at least one of the following is true: (a) the metal complex emits light upon photoexcitation at room temperature; wherein the emitted light has an emission spectrum characterized by a peak emission wavelength λ max when measured at a mass concentration of 1% in a PMMA film; wherein the metal complex has a λ max in the range of 400-500 nm and a VDR value of equal or less than 0.15, or the metal complex has a λ max in the range of 500-590 nm and a VDR value of equal or less than 0.15, or the metal complex has a λ max in the range of 590-700 nm and a VDR value of equal or less than 0.10, or (b) the OLED comprises a second host that is not deuterated, partially deuterated, or fully deuterated; and wherein at least one of the following conditions is true: (1) the metal complex is a Pt complex comprising a metal-carbene bond; (2) the metal complex comprises at least one feature selected from the group consisting of: an imidazole moiety; a fused or unfused heteroaryl moiety comprising at least two heteroatoms; a fused-ring structure comprising at least three rings, including at least one 6-membered heteroaryl ring; a fused-ring structure having at least four rings; a pendant group comprising at least three 6-membered aromatic rings, each of which is not directly fused to another of the at least three 6-membered aromatic rings; a partially or fully deuterated 5- or 6-member carbocyclic or heterocyclic ring directly bonded to the metal; a carbazole moiety which is directly bonded to the metal; a total of at least six 6-membered aromatic rings; at least one boron atom; at least one fluorine atom; a fused ring structure comprising a benzene ring directly bonded to the metal; or a substituted or unsubstituted acetylacetonate ligand; a silicon atom; a ring structure comprising 7 or more atoms; (3) the metal complex is a tetradentate Pt complex, wherein the tetradentate ligand forms at least three adjacent 5-membered or 6-membered chelate rings with at least two neighboring chelate rings being the same size; (4) the metal complex is a tetradentate Pt complex, wherein the tetradentate ligand comprises at least one coordinating oxygen atom or sulfur atom trans to a coordinating carbon atom; (5) the metal complex is partially or fully deuterated; (6) the metal complex comprises a metal selected from the group consisting of Os, Ag, Au, Cu, and Pd; (7) the metal complex is an Ir(III) complex comprising three different bidentate ligands; (8) the metal complex emits light upon photoexcitation at room temperature; wherein the emitted light has an emission spectrum characterized by a peak emission wavelength λ max when measured at a mass concentration of 1% in a PMMA film; wherein the metal complex has a λmax in the range of 400-500 nm and a vertical dipole ratio (VDR) value of equal or less than 0.15, or the metal complex has a λmax in the range of 500-590 nm and a VDR value of equal or less than 0.15, or the metal complex has a λ max in the range of 590-700 nm and a VDR value of equal or less than 0.10; (9) the metal complex has a lowest triplet energy T1 em and a lowest singlet energy S1 em , wherein the difference between S1 em −T1 em is equal or less than 0.3 eV; (10) the first host comprises a partially or fully deuterated moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene); (11) the first host comprises a boryl moiety; (12) the first host has a lowest triplet energy T1 host and a lowest singlet energy S1 host , wherein the difference between S1 host −T1 host is equal or greater than 0.25 eV, and equal or less than 1.50 eV; (13) the metal complex is a Pt complex and the first host has a lowest triplet energy T1 host and a lowest singlet energy S1 host , wherein the difference between S1 host −T1 host is equal or less than 0.30 eV; (14) the first host is the only host material in the emissive layer, and the first host comprises a heteroaryl group comprising at least two nitrogen atoms; (15) the metal complex emits light upon photoexcitation at room temperature; wherein the emitted light has an emission spectrum characterized by a peak emission wavelength λ max when measured at a mass concentration of 1% in a PMMA film; and wherein the full width at half maximum of the emission at λ max is equal to or less than 40 nm; (16) the metal complex emits light upon photoexcitation at room temperature; wherein the emitted light has an emission spectrum characterized by a peak emission wavelength λ max when measured at a mass concentration of 1% in a PMMA film; wherein the λ max is in the range of 700-1000 nm with a PLQY value of at least 30%; (17) the emissive layer contains two or more materials, which form an exciplex; (18) the OLED further comprises at least one additional layer comprising at least one partially or fully deuterated material; (19) the OLED has a first device lifetime LT95 which is measured at 10 mA/cm 2 , wherein the first device lifetime is at least 1.5 times greater than a second device lifetime which was obtained under the exact condition as the first device lifetime except the first host is non-deuterated; (20) at least one of the anode, the cathode, or an additional layer disposed over the emissive layer functions as an enhancement layer; wherein the enhancement layer comprises a plasmonic material exhibiting surface plasmon resonance that non-radiatively couples to the first phosphorescent emitter and transfers excited state energy from the emitter material to non-radiative mode of surface plasmon polariton; wherein the enhancement layer is provided no more than a threshold distance away from the emissive layer; and wherein the first phosphorescent emitter has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer and the threshold distance is a distance where the total non-radiative decay rate constant is equal to the total radiative decay rate constant; (21) the concentration level of the metal complex in the emissive layer along a direction extending perpendicular to the anode toward the cathode, follows a predefined non-constant gradient profile; and (22) any combination of two or more conditions listed above.

2 . The OLED of claim 1 , wherein the metal complex is a Pt complex comprising a metal-carbene bond; or the metal complex comprises at least one polydentate ligand that forms a 5-membered chelate ring with the Pt.

3 . The OLED of claim 2 , wherein the at least one polydentate ligand is a tetradentate ligand, wherein the 5-membered chelate ring can include a carbene bond.

4 . The OLED of claim 3 , wherein the carbene is substituted by a substituent R, wherein the substituent R is partially or fully deuterated.

5 . The OLED of claim 4 , wherein the substituent R comprises at least two 6-membered aromatic rings, each of which is not directly fused to the other 6-membered aromatic ring.

6 . The OLED of claim 1 , wherein the metal complex comprises at least one feature selected from the group c

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Thompson Nicholas J
• Brooks Jason
• Milas Ivan
• Feldman Jerald
• Talluri Siva Kumar
• Paudyal Mahesh
• Williams Douglas
• Margulies Eric A
• Lin Chun
• Ma Bin

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title