# US 2019/0378982 A1 · Organic mixture, composition, organic electronic device and application

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- Number: US 2019/0378982 A1
- Document ID: US20190378982A1
- Status: Published application
- Kind: A1
- Application number: 16/463,341
- Filed: 2017-11-23
- Published: 2019-12-12
- Earliest claimed: 2016-11-23
- Assignees: Guangzhou Chinaray Optoelectronic Materials Ltd.
- Applicants: Guangzhou Chinaray Optoelectronic Materials Ltd.
- Inventors: Ruifeng HE; Peng SHU; Yini LI; Junyou PAN
- Web page: https://patentgrep.com/patent/US20190378982A1

## CPC

- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 487/04: Ortho-condensed systems
- C07F 5/027: {Organoboranes and organoborohydrides}
- C09K 11/00: Luminescent materials, e.g. electroluminescent or chemiluminescent
- C09K 11/06: containing organic luminescent materials
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/624: {containing six or more rings}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/658: {Organoboranes}
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 2101/10: Triplet emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An organic mixture, comprising a first organic compound and a second organic compound that forms an exciplex with the first organic compound. The first organic compound is an aromatic compound containing a triphenylboron heterocycle, and the second organic compound is a compound containing an aromatic fused heterocycle. LUMOH1, HOMOH1 and ET(H1) are respectively defined as the lowest unoccupied orbital, highest occupied orbital and triplet energy levels of the first organic compound, and LUMOH2, HOMOH2 and ET(H2) are respectively defined as the lowest unoccupied orbital, highest occupied orbital and triplet energy levels of the second organic compound, min((LUMOH1−HOMOH2, LUMOH2−HOMOH1)≤min(ET(H1), ET(H2))+0.1 eV.

## Claims

### Claim 1

An organic mixture comprising a first organic compound and a second organic compound that forms an exciplex with the first organic compound, the first organic compound is an aromatic compound containing a triphenylboron heterocycle, the second organic compound is a compound containing an aromatic fused heterocycle, and LUMOH1 is defined as the lowest unoccupied molecular orbital energy level of the first organic compound, HOMOH1 is defined as the highest occupied molecular orbital energy level of the first organic compound, ET(H1) is defined as the triplet excited state energy level of the first organic compound, and LUMOH2 is defined as the lowest unoccupied molecular orbital energy level of the second organic compound, HOMOH2 is defined as the highest occupied molecular orbital energy level of the second organic compound, ET(H2) is defined as the triplet excited state energy level of the second organic compound, wherein, min((LUMOH1−HOMOH2, LUMOH2−HOMOH1)≤min(ET(H1), ET(H2))+0.1 eV.

### Claim 2 (depends on 1)

The organic mixture of claim 1, wherein, the first organic compound has the following structural formulas:
wherein, -L- is one selected from a single bond, a double bond and a triple bond, or L is one selected from the group consisting of an aromatic group with a ring atom number of 5 to 30 and a heteroaromatic group with a ring atom number of 5 to 30;
Ar1 is one selected from the group consisting of an aromatic group with a ring atom number of 5 to 60 and a heteroaromatic group with a ring atom number of 5 to 60;
—Z1—, —Z2— and —Z3— are each independently selected from the group consisting of none, —N(R)—, —C(R)2—, —Si(R)2—, —O—, —C═N(R)—, —C═C(R)2—, —P(R)—, —P(═O)R—, —S—, —S═O— and —SO2—, and at most two of —Z1—, —Z2— and —Z3— are none; R is one selected from the group consisting of H, D, F, CN, alkenyl, alkynyl, nitrile group, amino, nitro, acyl, alkoxy, carbonyl, sulfonyl, C1˜30 alkyl, C3˜30 cycloalkyl, an aromatic hydrocarbyl with a ring atom number of 5 to 60, and an aromatic heterocyclic group with a ring atom number of 5 to 60.

### Claim 3 (depends on 2)

The organic mixture of claim 2, wherein, the structural formula of Ar1 is one selected from the group consisting of
wherein, A1, A2, A3, A4, A5, A6, A7 and A8 are each independently selected from CR3 and N;
Y1 and Y2 are each independently selected from the group consisting of CR4R5, SiR4R5, NR3, C(═O), S and O;
R3, R4 and R5 are each independently selected from the group consisting of H, D, a linear alkyl with a carbon atom number of 1 to 20, a branched alkyl with a carbon atom number of 1 to 20, a cyclic alkyl with a carbon atom number of 1 to 20, an alkoxy with a carbon atom number of 1 to 20, a thioalkoxy with a carbon atom number of 1 to 20 and a silyl with a carbon atom number of 1 to 20, a ketone group with a carbon atom number of 1 to 20, an alkoxycarbonyl group with a carbon atom number of 1 to 20, an aryloxycarbonyl with a carbon atom number of 7 to 20, cyano, carbamoyl, haloformyl, formyl, isocyano, an isocyanate group, a thiocyanate group, an isothiocyanate group, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, an aryl containing 5 to 40 ring atoms, a heteroaryl containing 5 to 40 ring atoms, an aryloxy containing 5 to 40 ring atoms and a heteroaryloxy containing 5 to 40 ring atoms.

### Claim 4 (depends on 3)

The organic mixture of claim 3, wherein, Ar1 is one selected from the group consisting of
wherein, H on the ring may be arbitrarily substituted.

### Claim 5 (depends on 2)

The organic mixture of claim 2, wherein, the L is one selected from the group consisting of
wherein, C—X1—C, C—X2—C and C—X3—C are each independently selected from the group consisting of C—N(R)—C, C—C(R)2—C, C—Si(R)2—C, C—O—C, C—C═N(R)—C, C—C═C(R)2—C, C—P(R)—C, C—P(═O)R—C, C—S—C, C—S═O—C, C—SO2—C and C—C, and at most one of C—X2—C and C—X3—C is C—C.

### Claim 6 (depends on 2)

The organic mixture of claim 2, wherein, the first organic compound is one selected from the group consisting of

### Claim 7 (depends on 2)

The organic mixture of claim 2, wherein, the Ar1 is one selected from the group consisting of an aromatic group with a ring atom number of 5 to 60 containing an electron-accepting group, and a heteroaromatic group with a ring atom number of 5 to 60 containing an electron-accepting group.

### Claim 8 (depends on 7)

The organic mixture of claim 7, wherein, the electron-accepting group is one selected from the group consisting of F, CN,
wherein, g1, g2, g3, g4, g5, g6, g7 and g8 are each independently one selected from C and N, and at least one of g1, g2, g3, g4, g5, g6, g7 and g8 is N.

### Claim 9 (depends on 1)

The organic mixture of claim 1, wherein, the structural formula of the second organic compound is one selected from
wherein, L1 is one selected from the group consisting of an aromatic group with a ring atom number of 5 to 60, and a heteroaromatic group with a ring atom number of 5 to 60;
-L2- is a single bond, or L2 is one selected from the group consisting of an aromatic group with a ring atom number of 5 to 30, and a heteroaromatic group with a ring atom number of 5 to 30;
are each independently selected from the group consisting of an aromatic group with a ring atom number of 5 to 30, and a heteroaromatic group with a ring atom number of 5 to 30;
—X1— is a single bond, or one selected from the group consisting of N(R), C(R)2, Si(R)2, O, C═N(R), C═C(R)2, P(R), P(═O)R, S, S═O or SO2;
—X2—, —X3—, —X4—, —X5—, —X6—, —X7—, —X8— and —X9— are each independently selected from the group consisting of a single bond, —N(R)—, —C(R)2—, —Si(R)2—, —O—, —(C═N(R6))—, —(C═C(R6)2)—, —P(R6)—, —(P(═O)R6)—, —S—, —(S═O)— and —(SO2)—, and at most one of —X2— and —X3— is a single bond, at most one of —X4— and —X5— is a single bond, at most one of —X6— and —X7— is a single bond, and at most one of —X8— and —X9— is a single bond;
R1, R2 and R6 are each independently selected from the group consisting of H, D, F, CN, alkenyl, alkynyl, nitrile group, amino, nitro, acyl, alkoxy, carbonyl, sulfonyl, C1˜30 alkyl, C3˜30 cycloalkyl, an aromatic hydrocarbyl with a ring atom number of 5 to 60, and an aromatic heterocyclic group with a ring atom number of 5 to 60;
m is any integer from 1 to 4.

### Claim 10 (depends on 9)

The organic mixture of claim 9, wherein,
are each independently selected from the group consisting of
wherein, H on the ring may be arbitrarily substituted.

### Claim 11 (depends on 9)

The organic mixture of claim 9, wherein, the L1 and L2 are each independently selected from the group consisting of
wherein, C—X1—C, C—X2—C and C—X3—C are each independently selected from the group consisting of C—N(R)—C, C—C(R)2—C, C—Si(R)2—C, C—O—C, C—C═N(R)—C, C—C═C(R)2—C, C—P(R)—C, C—P(═O)R—C, C—S—C, C—S═O—C, C—SO2—C and C—C, and at most one of C—X2—C and C—X3—C is C—C.

### Claim 12 (depends on 9)

The organic mixture of claim 9, wherein, the second organic compound is one selected from the group consisting of

### Claim 13 (depends on 1)

The organic mixture of claim 1, wherein, at least one of the first organic compound and the second organic compound satisfies ((HOMO−(HOMO−1))≥0.2 eV, (HOMO−1) is defined as the second highest occupied molecular orbital energy level.

### Claim 14 (depends on 1)

The organic mixture of claim 1, wherein, the difference between the sublimation temperature of the first organic compound and that of the second organic compound does not exceed 30 K.

### Claim 15 (depends on 1)

The organic mixture of claim 1, wherein, the organic mixture further comprises an organic functional material selected from the group consisting of a hole injection material, a hole transport material, a hole blocking material, an electron injection material, an electron transport material, an electron blocking material, an organic host material and a light-emitting material.

### Claim 16 (depends on 1)

A formulation comprising the organic mixture of claim 1 and an organic solvent.

### Claim 17 (depends on 1)

An organic electronic device comprising a functional layer, wherein the material of the functional layer comprises the organic mixture of claim 1.

### Claim 18 (depends on 17)

The organic electronic device of claim 17, wherein, the organic electronic device is one selected from the group consisting of an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting electrochemical cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, and an organic spintronic device, an organic sensor and an organic plasmon emitting diode.

### Claim 19 (depends on 17)

The organic electronic device of claim 17, wherein, the organic electronic device is an organic light-emitting diode, and the functional layer is a light-emitting layer.

### Claim 20

(canceled)

### Claim 21 (depends on 2)

The organic mixture of claim 2, wherein the first organic compound is one selected from the group consisting of