ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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IPC분류정보
국가/구분
United States(US) Patent
공개
국제특허분류(IPC7판)
H01L-051/00
C09K-011/02
C09K-011/06
C07D-209/86
C07F-007/08
C07F-005/02
C07F-015/00
출원번호
17672934
(2022-02-16)
공개번호
20220181561
(2022-06-09)
발명자
/ 주소
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
출원인 / 주소
Universal Display Corporation
인용정보
피인용 횟수 :
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초록▼
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
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.
대표청구항▼
1. An organic electroluminescent device (OLED) comprising: an anode;a cathode; andan 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
1. An organic electroluminescent device (OLED) comprising: an anode;a cathode; andan 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; andwherein 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 λmax 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 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 T1em and a lowest singlet energy S1em, wherein the difference between S1em−T1em 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 T1host and a lowest singlet energy S1host, wherein the difference between S1host−T1host 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 T1host and a lowest singlet energy S1host, wherein the difference between S1host−T1host 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 λmax when measured at a mass concentration of 1% in a PMMA film; and wherein the full width at half maximum of the emission at λmax 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 λmax when measured at a mass concentration of 1% in a PMMA film; wherein the 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/cm2, 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. (canceled) 4. 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. 5.-6. (canceled) 7. The OLED of claim 4, wherein the carbene is substituted by a substituent R, wherein the substituent R is partially or fully deuterated. 8.-230. (canceled) 231. The OLED of claim 7, 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. 232. The OLED of claim 1, wherein 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. 233. The OLED of claim 1, wherein 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, wherein the Pt and the tetradentate ligand form at least one 5-membered chelate ring and at least one 6-membered chelate ring. 234. The OLED of claim 233, wherein the Pt and the tetradentate ligand form a 5-membered chelate ring and two 6-membered chelate rings, or form two 5-membered chelate rings and one 6-membered chelate ring. 235. The OLED of claim 1, wherein 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, or the tetradentate ligand comprises at least one coordinating oxygen atom trans to a coordinating carbon atom. 236. The OLED of claim 1, wherein the metal complex emits light upon photoexcitation at room temperature; wherein the emitted light has an emission spectrum characterized by a peak emission wavelength λmax 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 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 λmax in the range of 590-700 nm and a VDR value of equal or less than 0.10. 237. The OLED of claim 1, wherein the first host comprises a boryl moiety that is a three-valence boron atom. 238. The OLED of claim 237, wherein the boron atom is in one of the rings' backbone, in two of the rings' backbones, or in three of the rings' backbones. 239. The OLED of claim 1, wherein the first host is at least 10% deuterated. 240. The OLED of claim 1, wherein the OLED comprises a second host that is not deuterated, partially deuterated, or fully deuterated. 241. The OLED in claim 1, wherein the metal complex is a platinum complex and the first host comprises a moiety selected from the group consisting of triazine, pyridine, pyrimidine, pyrazine, pyridazine, dibenzofuran, dibenzothiophene, aza-dibenzofuran, aza-dibenzothiophene, triphenylene, aza-triphenylene, carbazole, indolocarbazole, aza-carbazole, aza-indolocarbazole, silyl, and boryl. 242. The OLED of claim 1, wherein the metal complex comprises at least one moiety selected from the group consisting of a partially deuterated alkyl group, partially deuterated cycloalkyl group, a partially deuterated aryl or heteroaryl group, a fully deuterated alkyl group, and fully deuterated aryl or heteroaryl group. 243. The OLED of claim 1, wherein the first host is selected from the group consisting of wherein: each of X1 to X11 is independently C or N;L′ is a direct bond or is an organic linker;each YA is independently absent or, when present, is selected from the group consisting of O, S, Se, CRR′, SiRR′, NR, BR, BRR′;each of RA′, RB′, RC′, RD′, RE′, RF′, and RG′ independently represents mono-, up to the maximum substitutions, or no substitutions;each of R, R′, RA′, RB′, RC′, RD′, RE′, RF′, and RG′ is independently a hydrogen or a substituent selected from the group consisting of the General Substituents defined herein; andat least one R, R′, RA′, RB′, RC′, RD′, RE′, RF′, or RG′ comprises deuterium. 244. The OLED of claim 1, wherein the metal complex has a structure M(LA)p(LB)q(LC)r, wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M; and each of ligand LB and ligand LC is independently selected from the group consisting of: wherein: T is selected from the group consisting of B, Al, Ga, and In;each of Y1 to Y13 is independently selected from the group consisting of carbon and nitrogen;Y′ is selected from the group consisting of BRe, BReRf, NRe, PRe, P(O)Re, O, S, Se, C═O, C═S, C═Se, C═NRe, C═CReRf, S═O, SO2, CReRf, SiReRf, and GeReRf;Re and Rf can be fused or joined to form a ring;each Ra, Rb, Re, and Rd independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;each of Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, Rd, Re and Rf is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; andany two adjacent Ra, Rb, Re, Rd, Re and Rf can be fused or joined to form a ring or form a multidentate ligand. 245. The OLED of claim 1, wherein the second host is selected from the group consisting of wherein: each of X1 to X11 is independently C or N;each YA is independently absent or, when present, is selected from the group consisting of O, S, Se, CRR′, SiRR′, NR, BR, BRR′;each of RA′, RB′, RC′, RD′, RE′, RF′, and RG′ independently represents mono-, up to the maximum substitutions, or no substitutions;each of R, R′, RA′, RB′, RC′, RD′, RE′, RF′, and RG′ is independently a hydrogen or a substituent selected from the group consisting of the General Substituents defined herein; andat least one R, R′, RA′, RB′, RC′, RD′, RE′, RF′, or RG′ comprises deuterium. 246. An organic electroluminescent device (OLED) comprising, an anode;a cathode; andan emissive layer, disposed between the anode and the cathode;wherein the emissive layer comprises a first compound and a second compound;wherein the first compound and the second compound form an exciplex;wherein the first compound is not an organometallic compound; andwherein the first compound is fully or partially deuterated, with the proviso that neither the first nor second compound is:
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