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US-12624055-B2 - Organic electroluminescent materials and devices

US12624055B2US 12624055 B2US12624055 B2US 12624055B2US-12624055-B2

Abstract

Provided are compounds having Formula I: wherein rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings; L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P(O)R, and GeRR′; a, b, c, d, e and f are each O for not present or 1 for present; each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent; and any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring. Also provided are formulations comprising these compounds. Further provided are OLEDs and related consumer products that utilize these compounds.

Inventors

  • Peter Wolohan
  • Tyler FLEETHAM
  • Hsiao-Fan Chen

Assignees

  • UNIVERSAL DISPLAY CORPORATION

Dates

Publication Date
20260512
Application Date
20220221

Claims (20)

  1. 1 . A compound having a structure of Formula I: wherein rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings; L 1 , L 2 , L 3 , L 4 , L′, and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P (O)R, and GeRR′; a, b, c, d, e and f are each 0 for not present or 1 for present; a+b+c and d+e+f are each greater than or equal to 2; with the proviso that the following two conditions are true: 1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and 2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring; each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.
  2. 2 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all aryl.
  3. 3 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is heteroaryl.
  4. 4 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all 6-membered rings.
  5. 5 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are each benzene rings.
  6. 6 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is a 5-membered ring.
  7. 7 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all single rings.
  8. 8 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is a fused ring.
  9. 9 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are each independently selected from the group consisting of benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.
  10. 10 . The compound of claim 1 , wherein L1, L2, L3, L4, L5, and L6 are each independently optionally present or being selected from the group consisting of O, S, NR, CRR′, and SiRR′, wherein R and R′ are each independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  11. 11 . The compound of claim 1 , wherein each of R1, R2, R3, R4, R5, and R6 are joined to its respective ring by a single bond and comprises hydrogen, deuterium, alkyl, heteroalkyl, pyrimidine, triazine, quinazoline, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, anthracene, triphenylene, pyridine, pyrazine, fluorene, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, triarylboryl, boraanthracene or quinoxaline, which may be further substituted.
  12. 12 . The compound of claim 1 , wherein each of R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of
  13. 13 . The compound of claim 1 , wherein one, two, or three of R1, R2, and R3 are not hydrogen, and the remainder of R1, R2, and R3 are hydrogen.
  14. 14 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
  15. 15 . The compound of claim 1 , wherein the compound is selected from the group consisting of: where R1, R2, R3, R4, R5 and R6 are independently comprising a structure selected from the group consisting of
  16. 16 . The compound of claim 1 , wherein the compound is selected from the group consisting of
  17. 17 . An organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula I: wherein rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings; L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P (O)R, and GeRR′; a, b, c, d, e and f are each 0 for not present or 1 for present; a+b+c and d+e+fare each greater than or equal to 2; with the proviso that the following two conditions are true: 1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and 2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR; R 1 , R 2 , R 3 , R 4 , R 5 , and Re are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring; each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.
  18. 18 . The OLED of claim 17 , wherein the compound is a host, and the organic layer is an emissive layer that comprises a phosphorescent emitter.
  19. 19 . The OLED of claim 17 , wherein the phosphorescent emitter is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of: wherein: T is selected from the group consisting of B, Al, Ga, and In; each of Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen; Y′ is selected from the group consisting of BR e , NR e , PRE, O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , P(O)R e , and GeR e R f ; R e and R f can be fused or joined to form a ring; each R a , R b , R c , and R d independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring; each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e R f , R a ′, R c ′, R B , and R N is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two adjacent substituents of R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
  20. 20 . A consumer product comprising an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula I: wherein rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings; L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SIRR′, P (O)R, and GeRR′; a, b, c, d, e and f are each 0 for not present or 1 for present; a+b+c and d+e+fare each greater than or equal to 2; with the proviso that the following two conditions are true: 1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and 2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring; each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.

Description

CROSS REFERENCE TO RELATED APPLICATION This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 63/154,858, filed on Mar. 1, 2021, the entire contents of which are incorporated herein by reference. FIELD The present disclosure generally relates to organometallic compounds and formulations and their various uses including as hosts or emitters in devices such as organic light emitting diodes and related electronic devices. BACKGROUND Opto-electronic devices that make use of organic materials are becoming increasingly desirable for various reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication opn a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively, the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single emissive layer (EML) device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art. SUMMARY In one aspect, the present disclosure provides a compound having the structure of Formula I: wherein rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;L1, L2, L3, L4, L5, and L6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P(O)R, and GeRR′;a, b, c, d, e and f are each 0 for not present or 1 for present;a+b+c and d+e+f are each greater than or equal to 2;with the proviso that the following two conditions are true: 1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and 2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR; R1, R2, R3, R4, R5, and R6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;each of R, R′, R1, R2, R3, R4, R5, and R6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two of adjacent R, R1, R2, R3, R4, R5, and R6 can be joined or fused to form a ring. In another aspect, the present disclosure provides an OLED having an organic layer comprising the compound as described herein. In yet another aspect, the present disclosure provides a consumer product comprising an OLED with an organic layer comprising the compound as described herein. In yet another aspect, the present disclosure provides a formulation comprising the compound as described herein. In yet another aspect, the present disclosure provides a chemical structure comprising the compound as described herein or a monovalent or polyvalent variant thereof. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows an organic light emitting device. FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer. DETAILED DESCRIPTION A. Terminology Unless otherwise specified, the below terms used herein are defined as follows: As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group a