# US 11,910,699 B2 · Organic electroluminescent materials and devices

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- Number: US 11,910,699 B2
- Document ID: US11910699B2
- Status: Granted
- Kind: B2
- Application number: 16/021,514
- Filed: 2018-06-28
- Published: 2019-02-14
- Granted: 2024-02-20
- Earliest claimed: 2017-08-10
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Peter Wolohan
- Web page: https://patentgrep.com/patent/US11910699B2

## CPC

- C07F 5/05: Cyclic compounds having at least one ring containing boron but no carbon in the ring
- C09K 11/06: containing organic luminescent materials
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/623: {containing five rings, e.g. pentacene}
- H10K 85/625: {containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 85/658: {Organoboranes}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/131: {with spacer layers between the electroluminescent layers}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 2101/10: Triplet emission
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present invention includes novel compounds containing hexaphenyl borazine or azahexaphenyl borazine substituted with heterocycles or azaheterocycles were disclosed in this application. These compounds are useful as host materials for phosphorescent electroluminescent devices.

## Claims

### Claim 1

A compound of Formula I:
wherein
groups A, B, C, D, E, and F are independently selected from hydrogen, deuterium or a structure of Formula II, wherein four to six of the groups A to F are independently a structure of Formula II;
T1, T2, T3, T4 and T5 are independently selected from N or CR, wherein no more than three of T1 to T5 can be N;
wherein R is selected from the group consisting of hydrogen, deuterium, halogen, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one of T1, T2, T3, T4 and T5 represents N and at least one of R includes a polycyclic group; or
each of T1, T2, T3, T4 and T5 represents CR and at least one R includes two polycyclic groups;
wherein each polycyclic group is selected from the group consisting of (a) a group selected from the group consisting of
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Y is selected from the group consisting of C and Si;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2;
(b)
wherein
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8;
Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; provided that when Z1 is O or S, then at least one of X1 to X8 is N; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
(c)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through Z1;
Z1 is N;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
at least one RX is heteroaryl;
(d)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 is NR or N,
wherein when Z1 is NR, Z2 is selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
wherein when Z1 is N, Z2 is selected from the group consisting of NR, BR, N, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof;
(e)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of BR, O, S, Se, CRfR2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
(f)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; provided that when one of Z1 and Z2 is N, then the other of Z1 and Z2 is not O.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R is selected from the group consisting of hydrogen, deuterium, cycloalkyl, heteroalkyl, amino, silyl, aryl, heteroaryl, nitrile, and combinations thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the at least one of R includes a polycyclic group selected from the group consisting of

### Claim 4 (depends on 1)

The compound of claim 1, wherein one T1 to T5 of the Formula II are independently N.

### Claim 5 (depends on 3)

The compound of claim 3, wherein Z1 and Z2 fare selected from the group consisting of O, S, and NR.

### Claim 6 (depends on 1)

The compound of claim 1, wherein each of the groups A, B, C, D, E, and F are independently a structure of the Formula II.

### Claim 7 (depends on 3)

The compound of claim 3, wherein the compound is of Formula III, Formula IV, or Formula V
wherein each RA to RF and each RA′ to RF′ are independently a representative group R.

### Claim 8 (depends on 7)

The compound of claim 7, wherein each RA to RF and each RA′ to RF′, are independently selected from the group consisting of hydrogen, deuterium, cycloalkyl, heteroalkyl, aryl, heteroaryl, amino, silyl, nitrile, and combinations thereof.

### Claim 9 (depends on 7)

The compound of claim 7, wherein each RA to RF and each RA′ to RF′, are independently selected from the group consisting of:
hydrogen;
aryl selected from the group consisting of phenyl, naphthyl, and partially or fully deuterated analogs of each thereof; each of which aryl is optionally substituted at a position ortho- to the bond to the hexaphenylborazine;
heteroaryl selected from the group consisting of pyridyl, pyrazinyl, pyrimidyl, triazinyl, carbazoyl, dibenzofuran, dibenzothiophene, benzimidazole[2,1-b]benzothiazole, 5H-benzimidazo[1,2-a]benzimidazole, benzimidazo[2,1-Mbenzoxazole, aza-carbazoyl, aza-dibenzofuran, aza-dibenzothiophene, aza-benzimidazole[2,1-b]benzothiazole, aza-5H-benzimidazo[1,2-a]benzimidazole and aza-benzimidazo[2,1-Mbenzoxazole, and partially or fully deuterated analogs of each thereof; each of which heteroaryl is optionally substituted at a position ortho- to the bond to the hexaphenylborazine;
wherein the substitution at the position ortho- to the bond to the hexaphenylborazine is a substituent selected from methyl, ethyl, propyl, i-propyl, or t-butyl, and partially or fully deuterated analogs of each thereof.

### Claim 10 (depends on 9)

The compound of claim 9, wherein one or more RA to RF or one or more RA′ to RF′ represent an aryl or a heteroaryl which is substituted at a position ortho- to the bond to the hexaphenylborazine.

### Claim 11 (depends on 2)

The compound of claim 2, wherein the compound is selected from the group consisting of

### Claim 12 (depends on 1)

The compound of claim 1, wherein the at least one of R includes a polycyclic group selected from the group consisting of:
(a) a group selected from the group consisting of
wherein
X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Y is selected from the group consisting of C and Si;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2, wherein the at least one polycyclic group is bonded to one of T2, T3, or T4 through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
(b)
wherein
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
the polycyclic group is bonded to one of T2, T3, or T4 through one of X1 to X8;
Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; provided that when Z1 is O or S, then at least one of X1 to X8 is N; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
(c)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the at least one of R includes two polycyclic groups.

### Claim 14 (depends on 1)

The compound of claim 1, wherein the at least one of R includes the polycyclic group
wherein
Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; provided that when Z1 is O or S, then at least two of X1 to X8 is N.

### Claim 15

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 is an emissive layer and the compound of Formula I is a host compound of Formula I:
wherein
groups A, B, C, D, E, and F are independently selected from hydrogen, deuterium or a structure of Formula II, wherein four to six of the groups A to F are independently a structure of Formula II;
T1, T2, T3, T4 and T5 are independently selected from N or CR, wherein no more than three of T1 to T5 can be N;
wherein R is selected from the group consisting of hydrogen, deuterium, halogen, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein one at least one of T1, T2, T3, T4 and T5 represents N and at least one of R includes a polycyclic group; or
each of T1, T2, T3, T4 and T5 represents CR and at least one R includes two polycyclic groups;
wherein each polycyclic group is selected from the group consisting of (a) a group selected from the group consisting of
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Y is selected from the group consisting of C and Si;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2;
(b)
wherein
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8;
Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; provided that when Z1 is O or S, then at least one of X1 to X8 is N; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
(c)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through Z1;
Z1 is N;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
at least one RX is heteroaryl;
(d)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 is NR or N,
wherein when Z1 is NR, Z2 is selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
wherein when Z1 is N, Z2 is selected from the group consisting of NR, BR, N, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof;
(e)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of BR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
(f)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; provided that when one of Z1 and Z2 is N, then the other of Z1 and Z2 is not O.

### Claim 16 (depends on 15)

The OLED of claim 15, wherein the organic layer further comprises a phosphorescent emissive dopant, wherein the emissive dopant 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 each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y1 is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
wherein Re and Rf are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each Ra, Rb, Rc, Rd, Re, and Rf is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.

### Claim 17 (depends on 15)

The OLED of claim 15, wherein the emissive layer further comprises an electron transport material (ETM) to enhance electron transport through the emissive layer; or
wherein the emissive layer further comprises a hole transport material (HTM) to enhance hole transport through the emissive layer.

### Claim 18

A consumer product comprising an organic light-emitting device comprising: an anode;
a cathode; and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of Formula I:
wherein
groups A, B, C, D, E, and F are independently selected from hydrogen, deuterium or a structure of Formula II, wherein four to six of the groups A to F are independently a structure of Formula II;
T1, T2, T3, T4 and T5 are independently selected from N or CR, wherein no more than three of T1 to T5 can be N;
wherein R is selected from the group consisting of hydrogen, deuterium, halogen, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one of T1, T2, T3, T4 and T5 represents N and at least one of R includes a polycyclic group; or
each of T1, T2, T3, T4 and T5 represents CR and at least one R includes two polycyclic groups;
wherein each the at least one polycyclic group is selected from the group consisting of (a) a group selected from the group consisting of
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Y is selected from the group consisting of C and Si;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2;
(b)
wherein
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8;
Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and
GeR1R2; provided that when Z1 is O or S, then at least one of X1 to X8 is N; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
(c)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through Z1;
Z1 is N;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
at least one RX is heteroaryl;
(d)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 is NR or N,
wherein when Z1 is NR, Z2 is selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
wherein when Z1 is N, Z2 is selected from the group consisting of NR, BR, N, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof;
(e)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of BR, O, S, Se, CR1R2, SiR1R2, and GeR1R2; and
R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
(f)
wherein
the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N; wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2; wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; provided that when one of Z1 and Z2 is N, then the other of Z1 and Z2 is not O.

### Claim 19 (depends on 18)

The consumer product of claim 18, wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display (display that is less than 2 inches diagonal), a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.

### Claim 20 (depends on 1)

A formulation comprising a compound according to claim 1.