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Equity | 12 Months Ended
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Dec. 31, 2023
Equity [Abstract] |
Equity | Dividends Holders of the Company’s common stock are entitled to receive dividends when and if they are declared by the Company’s board of directors. The Company’s board of directors declared quarterly cash dividends of $0.10 per share during 2023, payments for which totaled $60.3 million. The Company’s board of directors declared quarterly cash dividends of $0.10 per share during 2022, payments for which totaled $57.3 million. During 2021, the Company’s board of directors declared quarterly cash dividends of $0.08 per share, payments for which totaled $43.6 million. On January 17, 2024, the Company’s board of directors declared a quarterly cash dividend of $0.10 per share to be paid on February 21, 2024 to shareholders of record as of January 31, 2024. Future dividend declarations, if any, as well as the record and payment dates for such dividends, are subject to the final determination of the Company’s board of directors. Share Repurchase Program On December 14, 2020, the Company’s board of directors authorized a repurchase program, effective February 16, 2021, covering the repurchase of up to an aggregate of $125.0 million of the Company’s common stock, during a period of twelve months, in open market transactions and in accordance with one or more pre-arranged stock trading plans to be established in accordance with Rule 10b5-1 under the Securities Exchange Act of 1934, as amended. This repurchase program expired pursuant to its terms on February 15, 2022. In anticipation of its acquisition of CMC Materials, the Company suspended its previously announced share repurchase program in the fourth quarter of 2021. The Company did not repurchase any of its common stock in 2023 under a Board-authorized common stock repurchase plan. The Company did not repurchase any shares for the years ended December 31, 2023 and 2022, respectively, and repurchased $67.1 million of shares for the year ended December 31, 2021. The credit agreement governing the New Credit Facilities contains restrictions that may limit the Company’s ability to continue to repurchase shares in the future. 2020 Stock Plan In 2020, the Company’s board of directors and stockholders approved the Entegris, Inc. 2020 Stock Plan (the “2020 Stock Plan”). The 2020 Stock Plan replaced the Entegris, Inc. 2010 Stock Plan for future stock awards and stock option grants. The 2020 Stock Plan has a term of ten years and provides for the issuance of stock options and other share-based awards to selected employees, directors, and other individuals or entities that provide services to the Company or its affiliates. Under the 2020 Stock Plan, the board of directors or a committee selected by the board of directors will determine for each award, the term, price, number of shares, rate at which each award is exercisable and whether restrictions are imposed on the shares subject to the awards. The exercise price for option awards generally may not be less than the fair market value per share of the underlying common stock on the date granted. The 2020 Stock Plan provides that after December 31, 2019, any shares subject to stock awards that were awarded from the Company’s expired plans and that are forfeited, expired or otherwise terminated without issuance of shares will again be available for issuance under the 2020 Stock Plan. Stock Plan assumed from CMC Materials Subsequent to the acquisition of CMC Materials, the Company's Board of Directors approved the absorption of the CMC Materials 2021 Omnibus Incentive Plan (the “OIP”) into the Company's 2020 Stock Plan for the remainder of the term of the OIP Plan. The 2021 OIP provides for grants of equity awards in the form of stock options, restricted stock, restricted stock units, stock appreciation rights, performance-based awards, other stock-based awards such as substitute awards in connection with an acquisition, and cash incentive awards. 3.9 million additional shares became available for grant by the Company upon absorption of the OIP Plan. Each outstanding option to purchase shares of CMC Materials common stock under CMC Materials’ stock plan became an option to acquire, on the same terms and condition as were applicable under the CMC Materials stock plan, the Company’s common stock, with the number of shares and exercise prices thereof adjusted for the exchange ratio of 1.82. Accordingly, options to purchase 0.6 million shares of CMC Materials common stock were exchanged for options to purchase 1.2 million shares of the Company’s common stock. Each outstanding performance-based restricted stock unit of CMC Materials under CMC Materials’ stock plan became a time-based restricted stock unit with the same terms and conditions as were applicable under the CMC Materials stock plan, the Company’s common stock, with the number of shares and exercise price thereof adjusted for the exchange ratio of 1.82. Accordingly, 0.1 million shares of performance-based restricted stock units of CMC Materials common stock were exchanged for restricted stock units of 0.2 million shares of the Company’s common stock. For all plans, exclusive of the employee stock purchase plan, the Company had shares available for future grants of 10.2 million, 10.9 million, and 8.7 million shares at December 31, 2023, 2022 and 2021, respectively. Stock Options Stock option activity for the years ended December 31, 2023, 2022 and 2021 is summarized as follows:
| 2023 |  | 2022 |  | 2021
(Shares in thousands) | Number of shares |  | Weighted average exercise price |  | Number of shares |  | Weighted average exercise price |  | Number of shares |  | Weighted average exercise price
Options outstanding, beginning of year | 1,839 |  |  | $ | 62.59 |  |  | 657 |  |  | $ | 55.32 |  |  | 1,082 |  |  | $ | 33.38 |
Granted | 232 |  |  | 81.79 |  |  | 146 |  |  | 128.44 |  |  | 167 |  |  | 98.11 |
Assumed in CMC acquisition | — |  |  | — |  |  | 1,178 |  |  | 55.8 |  |  | — |  |  | — |
Exercised | (715) |  |  | 51.04 |  |  | (141) |  |  | 40.00 |  |  | (592) |  |  | 27.32 |
Cancelled or forfeited | (42) |  |  | 76.02 |  |  | (1) |  |  | 61.42 |  |  | — |  |  | — |
Options outstanding, end of year | 1,314 |  |  | $ | 71.83 |  |  | 1,839 |  |  | $ | 62.59 |  |  | 657 |  |  | $ | 55.32 |
Options exercisable, end of year | 900 |  |  | $ | 63.08 |  |  | 1,386 |  |  | $ | 54.53 |  |  | 111 |  |  | $ | 34.54 |
Options outstanding under the Company’s stock plans at December 31, 2023 are summarized as follows:
(Shares in thousands) | Options outstanding |  | Options exercisable
Range of exercise prices | Number outstanding |  | Weighted average remaining life in years |  | Weighted- average exercise price |  | Number exercisable |  | Weighted average exercise price
$0.00 to $31.10 | 99 |  |  | 1.5 years |  | $ | 27.45 |  |  | 99 |  |  | $ | 27.45 |
$31.11 to $43.47 | 164 |  |  | 2.4 years |  | 33.54 |  |  | 164 |  |  | 33.54 |
$43.48 to $55.72 | 200 |  |  | 3.3 years |  | 54.33 |  |  | 153 |  |  | 53.91 |
$55.73 to $80.00 | 303 |  |  | 5.4 years |  | 69.47 |  |  | 303 |  |  | 69.47 |
$80.01 to $128.44 | 548 |  |  | 5.1 years |  | 98.90 |  |  | 181 |  |  | 106.16 |
| 1,314 |  |  | 4.3 years |  | $ | 71.83 |  |  | 900 |  |  | $ | 63.08 |
The weighted average remaining contractual term for options outstanding and options exercisable for all plans at December 31, 2023 was 4.3 years and 3.9 years, respectively. Under the stock plans, the total pre-tax intrinsic value of stock options exercised during the years ended December 31, 2023 and 2022 was $29.2 million and $11.4 million, respectively. The aggregate intrinsic value, which represents the total pre-tax intrinsic value based on the Company’s closing stock price of $119.82 at December 31, 2023, which theoretically could have been received by the option holders had all option holders exercised their options as of that date, was $64.3 million and $51.6 million for options outstanding and options exercisable, respectively. Share-based payment awards in the form of stock option awards for 0.2 million, 0.1 million and 0.2 million shares were granted to employees during the years ended December 31, 2023, 2022 and 2021, respectively. Compensation expense is based on the grant date fair value. The awards vest annually over a period of four years and have a contractual term of 7 years. The Company estimates the fair value of stock options using the Black-Scholes valuation model. Key inputs and assumptions used to estimate the fair value of stock options include the grant price of the award, the expected option term, volatility of the Company’s stock, the risk-free rate and the Company’s dividend yield. Estimates of fair value are not intended to predict actual future events or the value ultimately realized by employees who receive equity awards, and subsequent events are not indicative of reasonableness of the original estimates of fair value made by the Company. The fair value of each stock option grant was estimated at the date of grant using a Black-Scholes option pricing model. The following table presents the weighted-average assumptions used in the valuation and the resulting weighted-average fair value per option granted for the years ended December 31, 2023, 2022 and 2021:
Employee stock options: | 2023 |  | 2022 |  | 2021
Volatility | 46.5 | % |  | 40.9 | % |  | 38.0 | %
Risk-free interest rate | 3.7 | % |  | 1.5 | % |  | 0.4 | %
Dividend yield | 0.5 | % |  | 0.3 | % |  | 0.3 | %
Expected life (years) | 4.7 |  | 4.2 |  | 4.6
Weighted average fair value per option | $ | 34.40 |  |  | $ | 43.47 |  |  | $ | 30.69 |
A historical daily measurement of volatility is determined based on the expected life of the option granted. The risk-free interest rate is determined by reference to the yield on an outstanding U.S. Treasury note with a term equal to the expected life of the option granted. Expected life is determined by reference to the Company’s historical experience. The Company determines the dividend yield by dividing the expected annual dividend on the Company’s stock by the option exercise price. Employee Stock Purchase Plan The Company maintains the Entegris, Inc. Amended and Restated Employee Stock Purchase Plan (“ESPP”). The ESPP allows employees to elect, at six-month intervals, to contribute up to 10% of their compensation, subject to certain limitations, to purchase shares of the Company’s common stock at a discount of 15% from the fair market value on the first day or last day of each six-month period. The Company treats the ESPP as a compensatory plan. At December 31, 2023, 1.1 million shares remained available for issuance under the ESPP. Employees purchased 0.2 million, 0.2 million and 0.1 million shares, at a weighted-average price of $68.87, $65.25, and $90.89 during the years ended December 31, 2023, 2022 and 2021, respectively. Restricted Stock Units Restricted stock units are awards of common stock made under the Stock Plans that are subject to a risk of forfeiture if the awardee terminates employment with the Company prior to the lapse of the restrictions. The value of such restricted stock units is determined using the market price on the grant date. Compensation expense for restricted stock units is generally recognized using the straight-line single-option method. A summary of the Company’s restricted stock unit activity for the years ended December 31, 2023, 2022 and 2021 is presented in the following table:
| 2023 |  | 2022 |  | 2021
(Shares in thousands) | Number of shares |  | Weighted average grant date fair value |  | Number of shares |  | Weighted average grant date fair value |  | Number of shares |  | Weighted average grant date fair value
Unvested, beginning of year | 844 |  |  | $ | 90.37 |  |  | 897 |  |  | $ | 62.69 |  |  | 1,083 |  |  | $ | 41.31 |
Granted | 640 |  |  | 80.45 |  |  | 366 |  |  | 117.82 |  |  | 293 |  |  | 101.04 |
Assumed in CMC acquisition | — |  |  | — |  |  | 155 |  |  | 92.96 |  |  | — |  |  | — |
Vested | (389) |  |  | 78.17 |  |  | (523) |  |  | 64.77 |  |  | (439) |  |  | 35.58 |
Forfeited | (90) |  |  | 89.23 |  |  | (51) |  |  | 85.16 |  |  | (40) |  |  | 57.39 |
Unvested, end of year | 1,005 |  |  | 89.08 |  |  | 844 |  |  | 90.37 |  |  | 897 |  |  | 62.69 |
During the years ended December 31, 2023, 2022 and 2021, the Company awarded performance-based restricted stock units for up to 0.2 million, 0.1 million and 0.1 million shares of common stock, respectively, to be issued upon the achievement of performance conditions under the Company’s stock plans to certain officers. Compensation expense is based on the grant date fair value. The awards vest on the third anniversary of the award date if the performance conditions have been satisfied. The Company estimates the fair value of the performance shares using a Monte Carlo simulation process. As of December 31, 2023, the total compensation cost related to unvested stock options, performance-based restricted stock units and restricted stock unit awards not yet recognized was $3.7 million, $3.1 million and $46.9 million, respectively, and is expected to be recognized over the next 2.5 years on a weighted-average basis. Modifications During the year ended December 31, 2022, the Company modified all employee awards of restricted share units, options, and performance-based restricted share units that were granted in the 2022 fiscal year to provide that the awards will generally vest in connection with the grantee’s qualifying retirement. The Company accounted for this as a modification of awards and recognized incremental compensation cost of $15.3 million. The incremental compensation cost was measured as the accelerated expense over the requisite service period. The fair-value-based measure of the modified awards was the same as the fair-value based measure of the original award immediately before modification because the modification only affects the service period of the award. During the years ended December 31, 2023 and 2022, the Company modified restricted share units, options, and performance-based restricted share units granted prior to the 2022 fiscal year for certain employees to accelerate the unvested awards upon their respective retirements from the Company. The Company accounted for this as a modification of awards and recognized incremental compensation cost of $0.7 million and $6.2 million for the years ended December 31, 2023 and 2022, respectively. The incremental compensation cost is measured as the excess of the fair value of the modified award over the fair value of the original award immediately before its terms modified and recognized as compensation cost on the date of the modification for the vested awards. Valuation and Expense Information The Company recognizes compensation expense for all share-based payment awards made to employees and directors based on their estimated fair values on the date of grant. Compensation expense is recognized using the straight-line attribution method to recognize share-based compensation over the service period of the award, with adjustments recorded for forfeitures as they occur. Awards issued to employees who are retirement eligible or nearing retirement eligibility are expensed on an accelerated basis. The following table summarizes the allocation of share-based compensation expense related to employee stock options, restricted stock awards, performance-based restricted stock awards and grants under the employee stock purchase plan for the years ended December 31, 2023, 2022 and 2021:
(In thousands) | 2023 |  | 2022 |  | 2021
Cost of sales | $ | 8,896 |  |  | $ | 5,780 |  |  | $ | 3,844 |
Engineering, research and development expenses | 7,999 |  |  | 4,596 |  |  | 3,504 |
Selling, general and administrative expenses | 44,476 |  |  | 56,201 |  |  | 22,536 |
Share-based compensation expense | $ | 61,371 |  |  | $ | 66,577 |  |  | $ | 29,884 |
Tax benefit | 12,472 |  |  | 13,977 |  |  | 5,488 |
Share-based compensation expense, net of tax | $ | 48,899 |  |  | $ | 52,600 |  |  | $ | 24,396 |

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